Ready to create lasting memories with your family on your next vacation? Whether it's a villa in Italy, learning to surf in Costa Rica, or a safari in Kenya, this article offers inspiration for multi-generational trips tailored to every age. From preschoolers to teens, discover exciting adventures paired with luxury accommodations, where we handle all the details, so you can focus on making memories. Explore ideas for your next escape that go beyond the typical family vacation.

Unforgettable Adventures for Every Generation

It's never too early to start planning your family's next adventure. We love brainstorming memory-making vacations that go beyond the typical kids' club.

Whether stargazing at a dark sky preserve or hiking national parks and hut-to-hut treks in the Appalachians or Alps, there's something for everyone—with five-star stays to top it off. We can handle all the details for multi-gen getaways, from tips on renting cribs to walking devices. Here's a bit of inspiration to get you started:

Preschoolers—Extended family getaways work for everyone. Grandparents get quality time with their kids and grandkids, and there are enough adults around that couples can take off and explore on their own.

Consider booking a villa in a new destination, such as the five-star Hotel Castello di Reschio in Umbria. A private pool and expansive grounds make it easy to entertain the kids—make sure to book a chef-run family cooking class together, too. Off-duty parents can escape into the rolling countryside to explore the wineries and villages. 

Middle Schoolers – Adventures are more accessible at this age; try a chalet for a week of skiing, where day-after-day instruction gives everyone a real chance to work on technique and improve.

Skill upgrades work in warmer climates, too – Costa Rica is an excellent spot for learning to surf, particularly from December to April. Long point breaks of warm tropical water – what's not to love?

Middle-school ages are also a great time for that first safari – book now for next summer's migration season in Kenya's Maasai Mara to see wildebeest and Zebra crossing the Mara River (and all the big cats that follow).

High schoolers and older – Older kids mean bigger adventures – safaris are great at this age, too, especially rugged gorilla trekking in Rwanda. The country offers incredible cultural experiences as well as unforgettable primate viewing.

Horse lovers and even city-slicker families looking for something completely different can make memories of getting their cowboy on at a guest ranch. Horseback riding, ATV rides through the woods, fly fishing—these all-inclusive stays include daily activities that give everyone a little breathing room and many opportunities to regale each other with adventures over bonfires and fine-dining dinners at the end of the day.

We can plan your clan’s getaway with ideas and locations that work for all ages and stages.

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