Planning a trip with multiple generations of your family? Before you book, listen to this essential episode! Travel advisors Ryan and Julie share hard-won wisdom about the most common mistakes families make when planning multi-gen vacations—and how to avoid them.

From the planning phase through your actual trip, they cover everything: why you need to nail down dates BEFORE contacting your travel advisor, the importance of having a "team leader" for your group, and why trying to do everything together is a recipe for stress (spoiler: those Disney families of 20 walking in a line aren't having as much fun as you think).

Discover why cruises and all-inclusives work so well for multi-gen groups, how to handle different budgets within the same family, and the critical conversation about who's paying for what. Julie shares real stories from her own family trips and client experiences, while Ryan offers practical tips about room configurations, meeting points, and making sure everyone's expectations are aligned.

The hosts emphasize that while planning some group activities is important, the magic often happens in the unplanned moments—cousins running to each other in the Magic Kingdom, spontaneous trivia sessions on the cruise ship, or simply sharing a meal together. They also tackle the delicate balance of ensuring the person treating the family doesn't have their preferences overlooked.

Whether you're planning a cruise, Disney vacation, or all-inclusive getaway with grandparents, siblings, and kids in tow, this episode will help you create a memorable trip that brings your family closer together—without the drama.

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