Tips for Planning a Multi-Generational Trip

Traveling with kids, parents, and grandparents can be one of the most rewarding experiences—but it also comes with its own set of challenges. In this episode of Vacation Mavens, Tamara and Kim are joined by travel expert Kirsten Maxwell, founder of Kids Are a Trip and Groups Are a Trip. With over 40 countries under her belt, Kirsten shares her best advice for planning stress-free multi-generational vacations, from cruises and resorts to vacation rentals and group tours.

Kirsten Maxwell is a travel expert and founder of Kids Are A Trip and Groups Are A Trip, who has turned her adventures across 40+ countries into inspiring travel resources. The best adventures happen when you travel with the people you love the most! You can follow Kirsten on Instagram and Facebook.

Whether you’re dreaming of a big family trip or just starting to plan, this episode is packed with tips on how to balance budgets, expectations, and activities so everyone—from toddlers to grandparents—has a memorable experience.

Episode Highlights:

• What “multi-generational travel” really means and the different ways families are making it work: "skip gen" (aka grandparents and grandchildren), grandparents, parents and kids, extended family with cousins, aunts and uncles
• Popular multi-gen trip types: cruises, vacation rentals, dude ranches, all-inclusive resorts, and group tours
• Family meetings (and honest conversations about budget and expectations) are key before you book
• Tips for managing food, chores, and shared expenses without stress
• How to balance mobility needs, activity levels, and different interests across age groups
• Favorite destinations for all-ages trips, including Lake Tahoe, Orlando, New York City, and all-inclusive resorts in Mexico and the Caribbean
• Why cruises and resorts with strong kids’ clubs make trips easier for parents and grandparents
• The benefits of guided family tours like Adventures by Disney, Tauck, and Backroads
• Money-saving tip: ask about group rates when booking cruises, resorts, or tours
• Practical advice for delegating trip planning (or hiring a travel advisor to take the pressure off)
• Travel gear pick: crossbody phone case with strap for safety and convenience