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- 🇺🇸US · Places & Travel#1925K to 30K
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1.5K to 9K🎙 Daily cadence·147 episodes·Last published 6d ago - Monthly Reach
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5K to 30K🇺🇸100% - Active Followers
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2K to 12K
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Recent episodes
How to Use Points, Cards and Travel to Save $19K on Flights, Hotels, and Honeymoon Travel Without Complicating Your Setup
May 20, 2026
Unknown duration
How to Unlock Unlimited 2-for-1 Flights with Southwest Companion Pass Using Points, Credit Cards, and Simple Planning
May 13, 2026
Unknown duration
9 Credit Card Mistakes Beginners Make That Kill Points Value and How to Turn Them Into Free Travel
May 6, 2026
Unknown duration
How to Turn Business Spending into Free Travel: Credit Card Points, Miles, and Smart Strategies for Military Members and Entrepreneurs
Apr 29, 2026
Unknown duration
How Danny Safran Turned Credit Card Points Into Family Trips, Luxury Hotels, and Europe Getaways Without Working in Travel
Apr 22, 2026
Unknown duration
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 5/20/26 | How to Use Points, Cards and Travel to Save $19K on Flights, Hotels, and Honeymoon Travel Without Complicating Your Setup | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 150 of Points, Cards and Travel, Ross Alcorn joins DeAndre Coke to break down how he turned everyday spending into nearly $20,000 in luxury travel using a simple, strategic approach to points and miles. If you’ve ever wondered how to maximize points and miles without overcomplicating your setup, this episode gives you a clear roadmap built on real results.Discover how Ross leveraged business expenses, group travel planning, and credit card strategy to fund business class flights, high-end hotels, and an unforgettable honeymoon experience. They dive into practical ways to earn points faster, avoid common mistakes, and use tools like loyalty programs, transferable points, and welcome bonuses to unlock outsized value. You’ll also learn how to approach real estate spending, vendor payments, and large life events like weddings as opportunities to accelerate rewards.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsDeAndre’s Social Media:InstagramLinkedInItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 5/13/26 | How to Unlock Unlimited 2-for-1 Flights with Southwest Companion Pass Using Points, Credit Cards, and Simple Planning | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 149 of Points, Cards and Travel, Ross sits down with Max Craig, also known as Points The Max, to break down the Southwest Companion Pass and how to use it to unlock massive travel value. If you’ve ever wondered how to turn one flight into two using points and miles, this episode gives you a clear and simple strategy to make it happen.Join us as we dive into how the Southwest Companion Pass works, who it makes sense for, and how to earn it using credit card points and smart timing. You’ll learn how to maximize points and miles through sign up bonuses, avoid common mistakes like poor timing, and build a long-term travel strategy that actually fits your lifestyle. We also cover repositioning flights, domestic travel planning, and how to combine Southwest with transferable points for bigger international trips.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsMax’s Social Media:InstagramFacebookWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 5/6/26 | 9 Credit Card Mistakes Beginners Make That Kill Points Value and How to Turn Them Into Free Travel | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 148 of Points, Cards and Travel, we break down the most common beginner credit card mistakes that quietly cost you thousands in travel rewards. If you’ve ever redeemed points for gift cards or picked the wrong card, this episode will help you fix those errors and start maximizing points and miles the right way.Join us as we walk through 9 key mistakes that beginners make when getting started with credit card points, from missing welcome bonuses to using the wrong card for everyday spending. You’ll learn how to align your card strategy with your actual spending habits, avoid interest charges that erase your rewards, and why transfer partners are the key to unlocking premium travel. We also cover when to use travel portals, when to book direct, and how to turn simple spending into high-value rewards. If you want to maximize points and miles without overcomplicating your setup, this episode gives you a clear path forward. Subscribe for more strategies to travel better and get more value from every dollar.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 4/29/26 | How to Turn Business Spending into Free Travel: Credit Card Points, Miles, and Smart Strategies for Military Members and Entrepreneurs | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 147 of Points, Cards and Travel, Ross sat down with Spencer Reese of Military Money Manual to break down how to turn everyday spending into powerful travel rewards using credit card points and smart business strategies. If you are a small business owner or in the military, this episode shows how to maximize points and miles without overcomplicating your setup while avoiding common mistakes that cost people thousands in missed travel value.Discover how credit card points can unlock business class flights, luxury hotels, and unforgettable trips worth thousands of dollars. We cover how to build a simple card strategy, why transferring points beats cash back, and how to leverage business expenses, welcome bonuses, and even large payments like taxes or rent to accelerate your rewards. From earning your first points to planning a $19,000 honeymoon almost entirely on points, this episode gives you a clear framework to travel better for less. Subscribe for more strategies to travel smarter and get more value from every dollar.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsSpencer's Social Media:InstagramYouTubeItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 4/22/26 | How Danny Safran Turned Credit Card Points Into Family Trips, Luxury Hotels, and Europe Getaways Without Working in Travel | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 146 of Points, Cards and Travel, Ross sits down with Danny Safran to break down how points and miles can create better family travel without needing a job in the travel industry. If you have ever wondered how to actually use points and miles in real life, this episode shows what it looks like to start small, stay consistent, and turn everyday spending into trips that feel bigger, easier, and far more affordable.Danny shares how one Hilton card sparked a full points and miles strategy that led to long weekend getaways, luxury stays, Europe travel, family vacations, and unforgettable sports trips. You will hear why beginners should not rush, how to avoid missing a sign up bonus, how hotel status can unlock more value, and why planning family travel well in advance changes everything. This conversation also covers Hyatt Globalist benefits, free night certificates, Rakuten, travel planning, and using rewards for the trips that matter most. Subscribe for more practical points and miles strategies that help you travel better for less.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 4/15/26 | The Power of Welcome Offers: How To Earn More Points, Avoid Bad Redemptions, and Turn Everyday Spend Into Luxury Travel | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 145 of Points, Cards and Travel, Ross breaks down how welcome offers can become one of the fastest ways to unlock better trips without increasing your travel budget. If you have ever wondered how people turn everyday spending into business class flights, luxury Hyatt stays, or free hotel nights, this episode explains the strategy in a simple, practical way. Ross walks through what welcome offers are, how minimum spend works, and why redemption value matters if you want to get real results from your points.Ross also shares real examples of using welcome offers for a honeymoon to Bali and Thailand, Hyatt redemptions, IHG free nights, and a British Airways booking made even better with transfer bonuses. Along the way, he explains how business owners can think strategically about higher-spend bonuses, why transferable points matter, and what mistakes to avoid if you want more value from your points and miles. If you want a smarter credit card strategy that leads to better travel, this episode gives you a strong starting point.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 4/8/26 | The Hardest Part of Points Travel: Finding Award Availability with Kyle Potter from Thrifty Traveler | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 144 of World Travel Made Easy, Ross Alcorn sits down with Kyle Potter from Thrifty Traveler to break down the biggest challenge in award travel today—finding award flights and business class availability before they disappear.As points and miles become more popular, airlines are releasing fewer premium seats to partners and using more dynamic pricing. Kyle explains how tools, alerts, and smarter strategies can help travelers still unlock incredible deals like business class flights to Asia, Europe, and the Caribbean using points. If you've ever struggled to find award flights despite having plenty of points, this episode will completely change how you approach travel planning.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsKyle’s Social Media:LinkedInItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 4/1/26 | Zero Percent Business Funding: How Entrepreneurs Use Credit Strategy, Higher Limits, and Smart Banking to Grow Without High Interest Debt | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 143 of Points, Cards and Travel, Ross Alcorn sits down with Michael Boly to break down how business owners can use a smarter business credit strategy to unlock 0% interest funding, access higher credit limits, and avoid expensive debt. If you have ever wondered how entrepreneurs use credit cards to create flexibility, improve cash flow, and still position themselves for premium rewards, this episode gives you the foundation first. Michael explains the biggest mistakes business owners make before applying, including high utilization, weak personal credit foundations, and low-limit personal cards that quietly cap future approvals. The conversation also covers how 0% interest funding really works, why banks approve these offers, and how business owners can use them responsibly for marketing, growth, renovations, and major expenses without relying on traditional loans. They also discuss balance transfers, personal guarantees, long-term banking relationships, and why better credit structure creates better opportunities.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsMichael’s Social Media:LinkedInItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 3/25/26 | The Hidden Strategy Behind Business Credit Cards: Use Spending, Billing Cycles, and Points to Unlock Travel and Business Flexibility | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 142 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with business expert David Barnett to break down how business credit card strategy can unlock travel rewards, improve cash flow, and create hidden financial advantages many entrepreneurs overlook.David spent years inside the American Express corporate card division and now helps people buy and sell businesses. In this conversation, he explains why most entrepreneurs think too small when it comes to business spending and credit cards. Instead of simply collecting points randomly, David shares how intentional planning can turn everyday expenses into meaningful travel rewards while also improving operating capital.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsDavid’s Social Media:YouTubeWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 3/18/26 | How Business Owners Use 0% Interest Credit Cards to Invest in Growth, Reduce Financial Stress, and Earn Travel Points Along the Way | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 141 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with stand-up comedian and business owner Scott Bedgood to discuss how entrepreneurs can use credit cards strategically to grow their business without taking on traditional loans.Scott shares how discovering 0% interest credit cards changed the way he invests in his speaking and coaching business. Instead of feeling pressured to generate immediate revenue after every expense, he now has the flexibility to make smart investments that support long-term growth. Ross also explains how points and miles strategy allows business owners to earn valuable travel rewards from expenses they already have. Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsScott’s Social Media:InstagramLinkedInItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
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| 3/11/26 | From One Card to Luxury Travel: How Smart Points Strategy Saved $4,000 on a Honeymoon | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 140 of World Travel Made Easy With Itinerary Boss, Ross Alcorn welcomes back Lauren Perussault to break down how a simple Points, Cards and Travel strategy turned everyday spending into a luxury honeymoon experience. After years of researching credit cards and feeling overwhelmed by options, Lauren finally implemented a clear strategy that helped her unlock thousands in travel value.By strategically opening the right credit cards before major wedding expenses, Lauren and her husband earned welcome bonuses that covered flights and significantly reduced the cost of their St. Lucia honeymoon. Using a combination of Chase points, Capital One points, and travel portal boosts, they saved over $4,000 on flights and a five star resort stay. The episode dives into how beginners can start building a Points, Cards and Travel system without spreadsheets or analysis paralysis. Ross and Lauren also discuss stacking benefits like airport lounge access, travel credits, and strategic card usage to maximize value from everyday spending.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsLauren’s Social Media:InstagramLinkedInItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 3/4/26 | Your First Female Solo Trip Blueprint: Safety Tips, Travel Trends, Travel Insurance, and Points Strategy with Henah Velez | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 140 of Points, Cards, and Travel, Ross Alcorn welcomes back Henah Velez to share solo female travel tips that help you feel safer, calmer, and more present on every trip. Join us as we break down travel trends 2026 listeners are already noticing, like digital detox travel, analog getaways, and choosing slower destinations over crowded viral hotspots.Henah shares solo female travel tips you can use immediately, including picking a safer location first, sharing your live location with someone you trust, reading reviews through a solo traveler lens, and arriving during daylight when possible. She also explains how to ease into your first solo trip with solo dates, short weekend test runs, and low pressure ways to meet people like walking tours and silent book clubs. Plus, we talk points and miles strategies that support safety and comfort, including flexible points, hotel credits, and why the Chase Sapphire Preferred is a strong beginner card. We close with a must do reminder on travel insurance and why Squaremouth can be worth it.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsHenah’s Social Media:InstagramNewsletterItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 2/25/26 | How she saved $4,000 on a United Kingdom and Ireland Trip Using Points: Transfer Partners, Sweet Spots, and Smarter Booking Tips with Lauren Ross | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 138 of Points, Cards, and Travel, Ross sits down with Lauren Ross to show how a simple credit card strategy can turn everyday spending into real travel. Discover how Lauren went from booking only through portals to confidently using points for flights, hotels, and high value perks, without making it a second job.Lauren breaks down her exact credit card strategy using Chase Ultimate Rewards, Amex Platinum benefits, and Hyatt points to cover a luxury stay in Dublin and book United premium economy home through Air Canada Aeroplan. You’ll hear how to evaluate “good deals,” why airline alliances matter, and when it is smarter to book directly instead of relying on a travel portal. She also shares how Amex Fine Hotels and Resorts credits can stack free breakfast and on property perks to cut cash costs fast. If you want a credit card strategy that feels attainable and repeatable, this episode is your roadmap. Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsLauren’s Social Media:InstagramItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 2/18/26 | BILT 2.0 Rewards Explained: How to use Rent and Mortgage Payments to fund free travel with Henah Velez | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 137 of Points, Cards, and Travel, join us as Ross Alcorn sits down with Henah Velez to make the BILT Card feel simple again. If you have rent or a mortgage and you want travel rewards without adding more complexity, this episode breaks down what matters, what changed, and how to think through it without getting stuck in the math.Henah shares how she originally got the Built Card as a renter paying around $4,000 in rent, why earning something beats earning nothing, and how she uses BILT points to book trips like Atlanta to Europe on Flying Blue promos, plus a 4.5K Alaska redemption that replaced a $400 cash ticket. They also unpack housing only vs BILT cash, how transaction fees really work, and why using a calculator can save you from guessing. If you want a cleaner credit card strategy that matches your real spending, this is your roadmap.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsHenah’s Social Media:InstagramNewsletterItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 2/11/26 | How Home Renovations With 0% APR Cards Funded a $6,000 Hawaii Trip on Points with Chris Reichenbach | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 136 of Points, Cards, and Travel, join us as Ross sits down with real estate investor Chris Reichenbach to show how points and miles can fund real travel while helping you move faster in business. If you are paying renovation costs by check or ACH, you might be missing a safer, more flexible way to pay, earn rewards, and keep projects moving.Chris shares how he went from fearing credit cards to using 0% APR business credit cards to cover materials, float expenses between hard money draws, and rack up points and miles without chasing random offers. You will hear how he handled a nightmare renovation that jumped to $140,000, why contractor payment methods matter, and how credit cards can protect you when work is not delivered. He also breaks down how he used points and miles to book a Hawaii trip that saved over $6,000 and created a life moment he will never forget.Credit Card Resources:5 Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsChris’s Social Media:InstagramYouTubeSpotifyItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 2/4/26 | How to Earn Maximum Credit Card Points, Hotel Room Block Rewards, and Plan a Stress-Free Destination Wedding with Kerry Krull (The Wedding App) | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 135 of World Travel Made Easy With Itinerary Boss, Ross sits down with Kerry Krull, founder of The Wedding App, to break down what actually makes destination weddings stressful and how couples can avoid it. Most destination weddings don’t fall apart because of travel costs or venues. They fail because guests don’t know what’s going on.Join us as Kerry shares insights from her background in corporate events and wedding planning, explaining why destination weddings should be treated like multi-day experiences, not just a single ceremony. From missed welcome parties to flight cancellations and last-minute schedule changes, Kerry explains how lack of communication creates chaos and how real-time updates can completely change the guest experience.Website: itineraryboss.comCredit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMelio: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Kerry’s Social Media:InstagramItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 1/28/26 | Why 40–50% of Flights Drop After Booking and How SkyKey Automatically Gets You the Difference Back with Jacob Goldberg, Co-Founder SkyKey | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 134 of World Travel Made Easy With Itinerary Boss, Ross sits down with Jacob Goldberg, co-founder of SkyKey, to break down one of the biggest hidden problems in airfare pricing and the simplest solution most travelers are missing.Airlines constantly change prices, and most travelers never check their ticket again after booking. Jacob explains why 40–50% of flights drop in price after purchase and how SkyKey monitors flights 24/7 to automatically secure refunds or flight credits when prices fall. With average savings of $130 per flight, SkyKey removes the stress of timing airfare purchases, deal alerts, and mental gymnastics especially for families, business travelers, and anyone booking peak travel dates.Website: itineraryboss.comCredit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMelio: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Jacob’s Social Media:InstagramItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 1/21/26 | Positioning Flights Explained: How to Unlock Business Class Awards From Any Airport with Hunter Threadgill from Professor of Points & Frequent Traveler University | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 133 of World Travel Made Easy With Itinerary Boss, Discover how positioning flights can turn “I don’t live near a hub” into real business-class options. Hunter Threadgill aka the Professor of Points breaks down what positioning flights are, why they work, and how to use them without blowing up your trip when delays happen.You’ll learn how to spot the best airports to position through (think Chicago, Boston, Seattle, Vancouver, and more), how to protect the long-haul seat you actually care about, and how to plan stress-free buffers especially when you’re on separate tickets or switching airports. Hunter also shares how he uses hotel points (like Hyatt and free-night certificates) to turn an overnight into a bonus vacation day, plus a simple way to think about fuel surcharges and smarter Europe gateways like Paris and Amsterdam. We also touch award availability patterns and why competition at “someone else’s hub” can create opportunities.Website: itineraryboss.comCredit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMelio: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Hunter’s Social Media:InstagramItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 1/14/26 | Simplify Tracking Your Points with AwardWallet: Reprice Flights & Avoiding Costly Mistakes With JT Genter of AwardWallet | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 132 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with JT Genter, Editor-in-Chief at AwardWallet, to break down how travelers can finally get organized with points and miles without spreadsheets, stress, or lost rewards. If you’ve ever forgotten expiration dates, redeemed points poorly, or felt overwhelmed managing multiple loyalty programs, this episode delivers clarity.Join us as JT shares how AwardWallet helps track credit card points, airline miles, hotel rewards, expiration alerts, and even flight repricing opportunities, all in one dashboard. You’ll hear how beginners can avoid analysis paralysis, how advanced travelers spot better redemptions, and why flexibility across programs leads to stronger value. JT also reveals common mistakes he sees, including why redeeming points for gift cards quietly destroys value.Website: itineraryboss.comCredit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMelio: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!JT’s Social Media:InstagramItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 1/7/26 | Credit Card Roadmapping Made Simple: Starter Cards, Premium Card Annual Fees, and Smarter Point Redemptions with Spencer Johnson | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 131 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with Spencer Johnson to break down how to build a simple, sustainable credit card strategy that actually leads to travel. Instead of chasing every shiny offer, Spencer explains how to start with the right foundation, choose cards that fit your real spending, and use transferable points to unlock better flights and hotels.This conversation covers annual fee math, welcome bonus timing, and why most people overcomplicate points and miles far too early. Spencer also explains how “cash back” cards can quietly become powerful travel tools, when diversification across banks actually helps, and how to avoid getting stuck with points you can’t use. If you want a clear roadmap whether you’re brand new or trying to clean up a messy setup, this episode delivers practical advice you can apply immediately. Subscribe to make sure you don’t miss future expert breakdowns.Website: itineraryboss.comCredit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMelio: Pay vendors who don't take card with credit card to earn more pointsFavorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Spencer’s Social Media:InstagramTiktokWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 12/31/25 | Southwest Companion Pass Explained: 135K Points Strategy, Companion Swap Rules, and Post-Change Reality with Max Craig (Points to the Max) | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 130 of World Travel Made Easy With Itinerary Boss, Ross sits down with Max Craig (“Points to the Max”) for a practical Southwest Companion Pass playbook that works in 2025 and 2026 without the timing mistakes that kill your value. Discover how the Southwest Companion Pass really works (true buy-one-get-one for just taxes and fees), why earning it early in the year can unlock up to 21+ months of upside, and how to approach the two-card method using P1/P2 strategy and the 24-month rules. Max also breaks down the recent Southwest changes, basic fare limits, fare multipliers, assigned seating, and bag fees and the simple math that can make a card’s annual fee pay for itself fast. You’ll also hear a smart repositioning flight framework (like Nashville → Chicago) to reach better international award deals, plus the most common Companion Pass pitfalls, spend tracker surprises, returns, and companion-change headaches (and why calling is often better).Website: itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus Notifications Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Max’s Social Media:InstagramFacebook PageWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 12/23/25 | Active Duty Credit Cards Rewards: No Annual Fee's, Smart Card Sequencing & Credits to Build Wealth and Book Luxury Vacations with Spencer Reese | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 129 of World Travel Made Easy With Itinerary Boss, we dive into the world of military credit cards with Spencer Rees from Military Money Manual. If you’re active duty, Guard/Reserve, or a military spouse, this episode shows how fee-waived premium cards can unlock premium travel, elite hotel status, and thousands in yearly savings. Learn exactly how to confirm MLA eligibility, why Amex Platinum and Chase Sapphire Reserve are the heavy hitters, and how to avoid the most common mistakes service members make with points and miles.Join us as Spencer breaks down the Military Lending Act, reveals the difference between active duty and veteran benefits, and shares real stories of flying business class on PCS moves, stacking hotel status overseas, and converting unused credits into real-life wealth (including Roth IRA contributions). You’ll also learn simple systems for batching credits, tracking cards, protecting your credit score, and maximizing rewards without overwhelm.Website: itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Spencer’s Social Media:InstagramYouTubeItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 12/17/25 | Simplify Finances First Before Credit Card Rewards: Banking Automation & High Yield Savings Foundation that Fuels Travel with Steve Domino | Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 128 of World Travel Made Easy With Itinerary Boss, Ross sits down with Steve Domino, co-founder of Crew, to show how a smart banking setup makes travel goals actually happen. Credit Card Points are only valuable when your money system is simple, automatic, and built to prevent overspending. Steve walks through Crew’s pockets, paycheck rules, joint accounts, and kid allowances so your bills, savings, and travel budget move themselves.Join us as we connect Credit Card Points strategy to real-life family finances: auto bill pay from a bills pocket, overspend protection tied to your budget, and a month-in-review that spotlights where to earn more. Crew offers a high-yield checking account (with Itinerary Boss code, a limited APY boost) and is building a smart charge card that pays down daily or weekly so you get rewards without carrying a balance. If you’ve tried tools like Greenlight, Monarch, or YNAB, Crew combines the pieces in one place for Points & Miles beginners and busy parents. Subscribe for more practical systems that help you travel more without debt.Website: itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Steve’s Social Media:LinkedInWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 12/10/25 | Family Slow Travel and World Schooling: How Business Owners Can Use of Credit Card Points for Extended Europe Travel with Suzy May | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 127 of World Travel Made Easy With Itinerary Boss, Ross sits down with money coach and podcaster Suzy May to break down how world schooling really works for regular families. You’ll hear how her family splits time between Colorado and Spain, why world schooling isn’t just for digital nomad influencers, and how the cost of preschool at home can equal a full school year abroad. If you’ve ever wondered whether world schooling and slow family travel are only for the ultra-rich, this conversation will fix that fast.They dig into choosing locations, navigating visas like Schengen and Mexico’s 180-day rule, and comparing real numbers on daycare, private schools, and programs like international schools or world schooling hubs. Then they tie it all back to points and miles, how slow travel uses fewer flights, why positioning flights and trains matter, and how business owners can turn everyday spending into long-haul family trips. If you want your kids learning from the world instead of just worksheets, this episode will give you a clear, practical roadmap.Website: itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Suzy’s Social Media:FacebookInstagramWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
| 12/3/25 | Hotel Upgrades, Elite Status Secrets & Free Night Certificates: How to Turn Every Stay Into a VIP Experience With Ben’s Big Deals | (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 126 of World Travel Made Easy With Itinerary Boss, we sit down with Ben from Ben’s Big Deals to break open the world of hotel upgrades and real-life elite status strategy. If you’ve ever wondered why some people always seem to snag better rooms, free nights, and special treatment, this hotel upgrade deep dive is your playbook.Ben shares how he went from La Quinta business trips to luxury stays using hotel upgrades, elite status, and smart use of free night certificates instead of just chasing flashy flights. You’ll learn why emailing the property before arrival matters, how ownership and brand relationships affect your stay, and when to pay cash vs. points. We get into IHG, Hyatt, Marriott, Hilton, best rate guarantees, elite status shortcuts, and how to think like a VIP guest without overcomplicating the game. If you want your next trip to feel like an intentional experience instead of a random hotel night, this is one you’ll want to replay and take notes on.Website: itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email listClickUp: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Ben’s Social Media:LinkedInWebsiteItinerary Boss Socials:LinkedInInstagramPinterestFacebook YouTube Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions. | — | ||||||
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