Image courtesy of The Dunlin, Auberge Resorts Collection
Pulling off a multi-generational trip isn’t for the faint of heart. It takes thoughtful planning and destination knowledge, plus a little bit of compromise. Destinations that work give everyone space to enjoy vacation at their own pace, then create space to share memorable moments.
But logistics can be tricky. Coordinating activities that work for toddlers through retirees, managing mobility needs, and finding properties with enough space that togetherness doesn't turn into claustrophobia—it's a lot. Your Fora Advisor handles all of it, so you can focus on the good stuff: making memories without the stress. Here are our top picks for trips where every generation can have their moment.
Maui, Hawaii
Image courtesy of Four Seasons Resort Maui at Wailea
Maui delivers that rare combination of accessibility and adventure that makes multi-generational travel memorable. The island's compact geography means shorter drives between activities, while the variety—from calm beach days to volcano hikes—ensures everyone finds their pace. Wailea's resort corridor offers the infrastructure families need: multiple dining options, reliable weather, and properties designed for groups with different energy levels.
Four Seasons Resort Maui at Wailea
The Wailea location is great for families juggling multiple generations. The resort is close to the airport so less time in the car, and it’s walkable to Wailea's shops and restaurants, so teens can shop or get ice cream without adults. The beach here is notably calmer than some of Maui's more dramatic coastlines, perfect for young swimmers and grandparents who prefer gentle waves.
The property's layout is easily navigable—no endless hikes between your room and breakfast. The complimentary Kids For All Seasons program (ages 5-12) offers genuine full-day engagement, giving parents and grandparents time to catch up. Multiple pool zones mean everyone can claim their territory: families congregate at the main pool, adults escape to the serenity pool, and romantics find the infinity edge overlooking the Pacific.
Why this works: Families with young children and grandparents who value convenience; groups seeking complimentary kids' programming; travelers who want beachfront calm without sacrificing amenities; golfers (Wailea's championship courses are minutes away).
Fairmont Kea Lani Maui
Every accommodation at Fairmont Kea Lani is a suite—a game-changing detail for families who need actual living space. The separate living areas give everyone breathing room, while the multi-bedroom villas with private plunge pools keep extended families under one roof without claustrophobia.
The pool complex features a 140-foot waterslide that younger kids adore. While the property sprawls more than the Four Seasons, that space translates to fewer crowds and more options for splitting up based on mood. The suite configuration also means kitchenettes for early morning coffee and late-night snacks, reducing the pressure of coordinating every meal as a group of twelve.
Why this works: Larger families needing multi-bedroom accommodations; groups with children under 10 who love water features; travelers who value in-room space over compact luxury; families who prefer the flexibility of kitchenettes.
South Carolina
Image courtesy of Montage Palmetto Bluff in Bluffton
The Lowcountry's gentle pace and coastal landscape create an ideal backdrop for multi-generational gatherings. South Carolina offers cultural richness without overwhelming itineraries—historic Charleston is a short drive from both properties. The region's temperate climate extends the travel season, and the Southern hospitality means service that genuinely accommodates families.
Montage Palmetto Bluff
Set within a 20,000-acre planned community, Montage Palmetto Bluff feels like a self-contained village. Grandparents gravitate toward the spa and peaceful riverside setting. Parents appreciate the Jack Nicklaus signature golf course and miles of biking trails. The Paintbox children's program (ages 5-12) keeps kids engaged with nature-based activities that feel distinctly Lowcountry.
The lagoon-style pool complex appeals universally—rare for resort pools that typically skew toward either families or sophisticates. Accommodation variety matters here: inn rooms suit couples, while multi-bedroom cottages with full kitchens keep extended families close but comfortable.
Why this works: Golfers and spa enthusiasts; families who want a resort that doesn't require leaving the property; groups seeking varied accommodation sizes; travelers drawn to Lowcountry charm and nature.
The Dunlin, Auberge Resorts Collection
The Dunlin's greatest asset for families is its proximity to Charleston—close enough for easy day trips, yet far enough to feel like a coastal retreat. The property invites families into nature without requiring extreme adventuring: tidal creek kayaking, crabbing from the dock, and beach exploration all happen at a leisurely Lowcountry pace.
What sets The Dunlin apart is the breadth of complimentary activities. House bikes, paddleboards, kayaks, fishing poles, beach gear, pickleball equipment—families can fill days without watching the bill climb. Daily programming includes mat Pilates, sunrise yoga, the "Takin' in the Crabs" ecology session, and goat farm tours.
Why this works: Extensive complimentary family activities; easy Charleston access for its restaurant and shopping scene; groups with different activity levels; families who value nature-based experiences over resort entertainment.
Colorado
Image courtesy of The Broadmoor
Colorado's alpine landscape delivers year-round appeal, transitioning seamlessly from summer hiking to winter skiing. The state's resort infrastructure is exceptionally family-oriented, with properties that have spent decades perfecting multi-generational hospitality.
The Broadmoor, Colorado Springs
The Broadmoor is a destination unto itself—an Italian Renaissance-style resort that's been perfecting family hospitality since 1918. The property spans activities across generations with seemingly effortless variety: fly fishing and championship golf for serious sportspeople, a complimentary movie theater and activity center called Play (with bowling, games and dining) for families who need indoor entertainment, and supervised kids' programs that range from art classes to outdoor exploration.
Multiple pools, a private lake with paddleboats and fishing, and proximity to Cheyenne Mountain Zoo mean families rarely need to leave the grounds. The dining spectrum runs from formal to poolside casual, accommodating both celebratory dinners and "we just need pizza" moments.
Why this works: Families seeking a comprehensive resort experience; groups with wide-ranging interests (from golf to zoo visits); travelers who prefer not to drive daily; multi-gen groups who want formal and casual dining under one roof; those who appreciate movie screenings and activity programming.
Sonnenalp Vail
Sonnenalp Vail brings Bavarian warmth to Colorado skiing, creating an atmosphere that feels more European family hotel than American ski resort. The location in Vail Village's heart means walkability—teens can grab hot chocolate independently, parents can find cocktails, and grandparents can stroll without coordinating shuttles.
The spa ranks among Vail's finest, giving adults genuine retreat space. Room configurations range from standard to multi-bedroom suites. Three on-site restaurants at varying formality levels mean you're never trapped by weather or exhaustion. The ski concierge handles equipment, lessons, and mountain logistics.
Why this works: Ski families with varying abilities; groups who appreciate European-style hospitality; travelers who prioritize spa quality; families wanting Vail Village walkability.
United Kingdom
Image courtesy of Gleneagles Townhouse
The UK's appeal for multi-generational travel lies in its layered history and gentle landscapes. British hospitality excels at accommodating families without infantilizing properties—you get refined service that welcomes children rather than merely tolerating them.
Gleneagles, Scotland
Gleneagles is Scotland's definitive multi-generational estate. Three championship golf courses satisfy serious players, while falconry, off-road driving, horseback riding, fishing, and clay shooting provide adventure for the less golf-inclined. The Den kids' club (ages 6-15, unsupervised) and Little Glen (ages 2-8, supervised) offer engaging programming, freeing parents and grandparents for spa time.
The estate's scale means you can stay on property for days without boredom. Multiple restaurants at different formality levels accommodate varying moods and occasions. The property manages to feel both grand and welcoming.
Why this works: Golf enthusiasts; families seeking a full-service estate experience; groups who want extensive on-site activities; travelers drawn to Scottish Highlands.
Heckfield Place, Hampshire
Heckfield Place offers an understated country house experience, like visiting a relative's gorgeous home. The Georgian estate centers around a working farm, giving children live interaction with animals. The 438 acres are great for walking and exploring, without requiring fitness extremes. Both indoor and outdoor pools mean you can swim in any weather, and the Marle Spa is a relaxing adult sanctuary.
Located close enough to London for easy access yet feeling upscale and rural, Heckfield Place works for families wanting wide open country spaces without isolation.
Why this works: Families interested in sustainable travel; groups with nature-curious children; travelers wanting proximity to London with countryside feel; grandparents who appreciate refined understatement.
Spain
Spain's combination of beaches, culture, and sophisticated infrastructure makes it exceptional for multi-generational European travel. The climate reliably delivers sunshine, and Spanish culture genuinely welcomes families.
Finca Cortesin Golf & Spa
Finca Cortesin sits on Spain's Costa del Sol and is tailored to families, with villas and a ton of resort amenities. The championship golf course ranks among Europe's finest. The Beach Club (accessible via a resort shuttle) features an infinity pool and gorgeous Mediterranean views, allowing families to split time between the resort and the beach.
Spacious villas, many with private pools and gardens, give extended families plenty of space. Supervised kids' programming, a tennis academy, multiple pools, and extensive grounds for biking keep children engaged, while adults unwind in one of Spain's premier spas.
Why this works: Golf-focused families; groups wanting villa privacy with resort amenities; travelers seeking beach and resort variety; families who value exceptional spa facilities.
St. Regis Mardavall Mallorca Resort
Just outside Palma with direct beach access, St. Regis Mardavall combines Mediterranean island appeal with the necessary family infrastructure. Proximity to Palma matters significantly—easy airport access and the capital's culture provide optional day trips without requiring long drives.
Multiple pools, extensive kids' programming, and an excellent spa mean families can stay put or explore based on daily energy levels. Championship golf nearby satisfies serious players.
Why this works: Families wanting beach access with luxury amenities; travelers who value proximity to Palma; golfers seeking championship courses; groups who appreciate St. Regis service standards.
Alaska: Princess Cruises
Princess strikes an ideal balance for multi-generational Alaska exploration. The Discovery at Sea Youth & Teen Centers are divided by age group. Complimentary and supervised, these programs give parents and grandparents freedom to explore without the littles in tow.
What distinguishes Princess for Alaska is their North to Alaska program, which features naturalists and park rangers who run wildlife and ecology talks. The Alaska itineraries typically include longer port stays, which helps passengers have a wider menu of excursions for all kinds of mobility levels and interests.
Why this works: Multi-gen groups who want to experience Alaska's grandeur without road trip logistics; families with varying ages (toddlers to retirees); travelers who appreciate nature-focused programming; groups looking for a refined vibe with family amenities.
Mediterranean: Celebrity Cruises
Celebrity represents the sweet spot for Mediterranean multi-generational travel—more sophisticated than mass-market lines yet offering excellent kids' clubs. Camp at Sea divides younger travelers by age groups with age-appropriate programming.
The Mediterranean itineraries typically feature longer port stays compared to other cruise lines, which helps when coordinating different interests and mobility levels. The ships themselves are architecturally striking with impressive dining programs and spa facilities that provide adult-only retreat space.
Why this works: Families who want to unpack once but experience different cultures; travelers with varying mobility levels (longer port stays); groups who prioritize excellent dining.