DTR 83: The Perfect 14-Day Walt Disney World Family Vacation | Dining Plan, Dessert Parties, PhotoPass, Jungle Cruise With Derek and Maddie & More

DTR 83: The Perfect 14-Day Walt Disney World Family Vacation | Dining Plan, Dessert Parties, PhotoPass, Jungle Cruise With Derek and Maddie & More

June 13, 2026 · 44 min

About this episode

Michaela shares her experience planning a perfect 14-day family vacation at Walt Disney World, including tips on dining, photo opportunities, and attractions.

Today we're joined by our friend Michaela, who recently took an incredible 14-day Walt Disney World vacation with her husband and four kids. From start to finish, she planned what might be the perfect family Disney trip, and she's sharing all the details with us. We talk about how she maximized the Disney Dining Plan, enjoyed some amazing character meals, strategically used Lightning Lanes, and invested in PhotoPass so Mom could actually be in the family photos instead of always taking them. She even hired a professional photographer for a beautiful family photo session at their resort. As a special bonus, we also got the chance to ride Jungle Cruise with Michaela and her family during their trip! This episode is packed with planning tips, Disney magic, and plenty of fun family memories. If you're dreaming about your next Walt Disney World vacation, you won't want to miss this one. Follow her @fromcastlestococktails and us @DisneyTripReportPod Please leave a review and support the show www.patreon.com/DisneyTripReportPod

People in this episode

Hosts: Derek Sasman, Madison Sasman

Guest: Michaela

Topics covered

Keywords

Mentioned in this episode

Organizations: Disney

Products: Disney Dining Plan, PhotoPass

Places: Walt Disney World

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