March 10, 2025
You want to bring your extended family together on an unforgettable trip, so you can foster deeper bonds and create cherished memories. The question is: where to go? Planning a multigenerational travel experience can get a little tricky, since you need to juggle complex logistics—and the different needs and interests—of a group of all ages traveling together.
But making the trip is so worth it. Here are three hot spots I highly recommend for a multigenerational family journey that will keep your entire family entertained:
1. Jumby Bay Island Resort, Antigua
This is one of the hands-down most luxurious properties in the world—and it happens to be extremely welcoming to families! If the main goal of your multigenerational escape is simply to relax together, head to Jumby Bay. The all-inclusive resort sits on its own private island and boasts wide swaths of sugar-white-sand beach and clear turquoise waters, perfect for young and old alike to wade out in.
With two-bedroom family suites and a plethora of gorgeous private villas, it’s easy to find the perfect set of accommodations for your group. Villas come with private pools and a dedicated butler, and you can even hire a private chef for a customized dining experience for you and your family (and you won’t be on dish duty!). Use bicycles to trek around the island, play a round at the tennis courts, try your hand at one of the watersports on offer, or drop the young ones off at the kids club to enjoy a grown-up afternoon to yourselves.
2. Four Seasons Resort and Residences Jackson Hole, Jackson Hole, Wyoming
For year round outdoor fun with the family, head to Jackson Hole. With the snow-capped Grand Tetons as the backdrop, Jackson Hole offers some of the best family-friendly skiing in the U.S.—and this sumptuous Four Seasons gets you close to the most exciting ski runs.
The property’s prime location means you’re also close to two national park gems: Grand Tetons and Yellowstone. Align your visit during the kids’ summer break schedule for some intrepid park exploring; the Four Seasons offers incredible outdoor experiences like a wildlife safari, rafting down Snake River, and even a private flight excursion to spot Yellowstone’s elusive grey wolves from above.
3. A Luxury Villa in Guanacaste, Costa Rica
A luxury villa rental is a fantastic choice for a big extended family escape. You have access to more privacy than you would at a resort or hotel, and the larger size of your villa gives you all plenty of room to spread out while still sharing common spaces—like a pool area and living room—that promote quality time together.
If your family is more of the adventurous sort, a villa stay in Costa Rica can’t be beat. I recommend the Guanacaste area; Costa Rica’s “Gold Coast” is known for its beautiful beaches and biodiverse national parkland. Endless adventure activities including surf lessons at the famous Playa Hermosa, hiking through rainforest to spot monkeys and sloths, ziplining through the jungle treetops, or even ATVing through the lush interior. If not everybody in your group is up for such high-octane activity, they can hang back at your luxurious villa and enjoy time at the pool!
Ready to plan your family’s escape?
VIP your experience by booking with me! Thanks to my industry connections and luxury affiliations, I’m able to get special perks and upgrades for my clients at incredible properties like these. Work one-on-one with me to design your personalized spa escape, or book yourself in a gorgeous property via my Virtuoso Booking Portal.
