Occasions
The best US destinations for a big group or reunion
How to plan a luxury trip for a big group, and the US destinations, private villas, and homes that make it effortless rather than chaotic.
The short answer
For a big group or reunion, the key is a private home with room to gather. The Big Island and Maui offer estate villas with space and beaches, Aspen suits a mountain gathering, and the Florida Keys are built for a waterfront house and days on the boat.
A big group trip lives or dies on the base. Get everyone under one beautiful roof with room to gather and space to escape, and the rest falls into place. Here is where that works best.
Hawaii, for estate villas
The Big Island and Maui have some of the country's best estate rentals, private pools, chefs, and beaches, with enough bedrooms and enough acreage that a large group never feels on top of itself.
Aspen, for a mountain gathering
For a winter reunion or a summer one, a private Aspen home puts everyone together with skiing, hiking, and a town full of tables just outside the door. It is the group trip with a view.
The Florida Keys, for the water
A waterfront home in the Keys turns a group trip into days on the boat, sunset dinners on the dock, and an easy, barefoot pace. It is the reunion that feels like a permanent vacation.
The secret to a great group trip is a house big enough that everyone can be together, and private enough that no one has to be.
Tell our planner your group and its needs, and it will build a dated plan around the right home, the chef, and the days out, sequenced and linked so one person is not left organizing everyone.
Your move
Turn this into a dated, bookable plan
Answer a few questions and get a day-by-day itinerary with a real pick and a booking link for every stay, table, and guide. Founding price, $29.
Common questions
What is the best destination for a large family reunion?
Hawaii's Big Island and Maui lead for estate villas with space and beaches, while Aspen and the Florida Keys suit mountain and waterfront gatherings respectively.
Is it better to rent a villa or book multiple hotel rooms for a group?
For most groups a private villa or estate wins: shared spaces to gather, a private pool, the option of a chef, and often a lower per-person cost than a block of suites.
How far ahead should you plan a big group trip?
Six to twelve months for peak seasons, since the best large homes are limited and book early. A concierge-built plan keeps the logistics from falling on one person.
