Photo: Stephen Andrews/Unsplash
Getting multiple generations to agree on a destination is the easy part. The real challenge is everything that follows: finding accommodations that work for a toddler, a teenager, and a grandparent with a bad knee; building an itinerary that doesn’t lose half the group by day two; managing the dietary restrictions, the room configurations, and the diplomatic minefield of who sits next to whom at dinner.
The key to success, according to Julie Noda, General Manager of Groups at Fora, is intentionality—in the physical space, the programming, and the hotel’s understanding of what it means to design for multiple generations at once. That means connecting rooms at hotels, spacious villas with full kitchens, a dinner menu that works equally well for a nine-year-old and a food-loving grandparent, and pools with a quiet adult corner and a splash zone within eyeline. “The best properties layer in programming that creates shared memories, whether that’s a guided nature walk, a beach bonfire, or a kids’ club,” says Noda. “Design, accommodation, and programming working in tandem is what turns a multigenerational group trip into a story the whole family tells for years.”
Not every property lends itself to a particular travel style, so we’re sharing a few advisor-loved options based on your group’s m.o.
For families with young kids
Image courtesy of Malliouhana
Malliouhana
Anguilla
The calm shallows of Meads Bay make Anguilla a natural fit for a multigenerational group trip that needs to work across every age, and Malliouhana leans into every advantage its setting affords. There’s the Mini-Explorers Kid’s Club for ages 5 to 12—kayaking, beach treasure hunts, steel pan drum lessons—plus overnight or hourly childcare and a family pool with splash pad. The culinary team is adept at navigating the dietary requirements a large group brings.
The Ritz-Carlton, Amelia Island
Amelia Island, Florida
The barrier island’s dune-lined beachfront is an easy sell across generations, and the Ritz-Carlton adds the programming to back it up: Ritz Kids for ages 5 to 12 (cooking classes, nature exploration, afternoon teas with a local bent), a separate teen activity track, and arranged beachside bonfires with blankets and s’mores that give a multigenerational group a natural gathering point to close out the day. The culinary team is well-practiced at managing the dietary range a large family tends to arrive with.
For families that love an action-packed itinerary
Image courtesy of Paws Up Montana
Paws Up Montana
Greenough, Montana
Spread across 37,000 acres along the Blackfoot River, Paws Up gives a multigenerational group the room to scatter without losing each other: fly fishing, horseback riding, and rafting for those who want full days in the field; guided nature walks and campfire programming in the evenings that pull everyone back together. The Michelin-recognized food ensures the group has something to look forward to at the end of every day.
Clayoquot Wilderness Lodge
British Columbia, Canada
The approach alone—by floatplane over miles of unbroken old-growth, or by boat through a sound so still it mirrors the treeline back at you—is enough to make every generation in the group go quiet at the same time. From there, the program fills itself in: old-growth forest trails, sea kayaking through coastal inlets, bears on the riverbanks, whales offshore, and three Michelin Keys’ worth of food and hospitality waiting at camp. For a multigenerational group with adventurous grandparents and older kids who need a trip to genuinely move them, the pairing of genuine wilderness immersion with hospitality at this level is rare enough to justify the journey.
For families that want an all-inclusive
Image courtesy of Hyatt Ziva Cap Cana
Hyatt Ziva Cap Cana
Cap Cana, Dominican Republic
The all-inclusive format resolves one of the more persistent tensions in group travel: who's covering what and when. Hyatt Ziva Cap Cana brings it to Juanillo Beach, with a pool complex that spans waterpark slides and calmer adult corners, and a restaurant lineup broad enough to satisfy every preference in the group. With everything on a single rate, the group can spend the day going in a dozen different directions and meet again for dinner without a word about who’s covering the tab
Carlisle Bay
Antigua
Tucked into Antigua’s quieter south coast, Carlisle Bay keeps a multigenerational group well clear of the major tourist areas while giving everyone something to do: the all-inclusive program covers meals at four restaurants, drinks, water sports, tennis, and a kids club that runs turtle-spotting boat trips and pizza-making sessions. For larger family groups that need the space, three-bedroom Carlisle Suites come with a full kitchen and living-dining area.
For families with accessibility needs
Image courtesy of Chatham Bars Inn
Chatham Bars Inn
Chatham, Massachusetts
This Cape Cod classic has occupied a 25-acre stretch of shoreline since 1914, and its character reflects that history: charming shingled buildings, ocean-facing porches wide enough to while away the afternoon, and grounds envelop guests in the coastal landscape. For multigenerational groups with accessibility needs, it's one of the more genuinely considered properties in New England—accessible rooms throughout, a zero-entry pool, an allergy-conscious kitchen, and an autism-friendly designation that goes beyond room categories. Summer Kids Crew sessions put younger guests directly into the Cape Cod setting—beach explorations, nature walks—while adults find their own version of the same.
Montage Palmetto Bluff
Bluffton, South Carolina
Set amid marshes, live oaks, and waterways you can explore by paddleboat, this Low Country resort’s cottage-style layout and flat, walkable terrain make it a natural fit for multigenerational groups where mobility varies across generations. The property is designed to be moved through together rather than around, with a spa, pools, golf, a culinary program, and outdoor programming that give every generation somewhere to settle in.
For families with large groups
Image courtesy of Susurros del Corazón, Auberge Resorts Collection
Evermore Orlando
Orlando, Florida
Few properties are specifically built with large groups in mind, but this sprawling complex was. Evermore Orlando is built from the start to accommodate them. Houses run five to eleven bedrooms—with private outdoor pools, game rooms, and home theaters—including ADA-accessible configurations that are difficult to find at this scale. Three miles from Walt Disney World, with a 20-acre private beach and 13 dining venues on-site, the resort gives a large group a complete itinerary without requiring anyone to leave the property.
Susurros del Corazón, Auberge Resorts Collection
Punta de Mita, Mexico
Barrier-free two- and three-bedroom villas—built for multigenerational groups where mobility needs span generations—are genuinely rare, and this compact property is one of the few properties on Mexico’s Pacific coast to offer them. Between the three outdoor pools, a kids club (Morritos) with surf immersion and cooking lessons, and villas that scale up to five bedrooms, large groups have plenty of room to spread out without losing each other.
Villas of Distinction
Global
An accessibility filter makes it easy to search the well-curated options for high-end rental properties suited to groups where mobility needs span generations. You might be tempted by a 16th-century Puglian palazzo with wheelchair access or a five-bedroom stunner on Crete with an open floor plan and three ground-level rooms that connect to a charming private garden that overlooks the sea.
Le Collectionist
Global
For groups that want full kitchens, shared living areas, and private outdoor space—rather than adjacent hotel rooms—Le Collectionist curates architecturally significant private villas, with accessible options available to filter for multigenerational groups where that matters. A Fora Advisor can narrow the search by size, location, and accessibility requirements and manage the rental process from first look to check-in.
How a travel advisor makes group travel easier
Booking accommodations for a multigenerational group involves more moving pieces than a standard reservation: multiple room types and accessibility requirements, varying budget expectations across the family, and more guests than any one person should have to coordinate. Room blocks—pre-negotiated sets of rooms held at a contracted rate—solve the availability problem, but the contracting and coordination that follow can become a full-time job of their own.
A Fora Advisor can manage the entire process: identifying properties with the right room mix and accessibility features for your specific group, submitting requests for proposal, negotiating rates, contract terms, and perks through Fora’s preferred partnerships, and making sure the fine print actually works in the group’s favor. Once the block is set, they handle individual bookings, confirmations, and cutoff-date reminders for every family member—one point of contact, no group chat required.
