Multi-generational trips can sound fun in theory, but when it comes to the planning stage, it can feel almost impossible to settle on a destination that meets everyone’s needs.
Fortunately, there are several strategies you can use to find spectacular places for a multi-gen vacation that will please everyone in your brood, from toddlers to teenagers and grandparents.
Here’s a look at unforgettable destinations for multigenerational trips, so you can cut straight to making memories as an extended family.
How to Choose a Destination for a Multi-Gen Trip
The first step to choosing a destination for a multi-gen group is to identify each family member’s needs, especially when it comes to each person’s activity level, according to luxury travel agency Red Savannah.
“Younger children will need lots of space to run and play, perhaps with a playground area close to the main house,” Red Savannah says. “A tennis court will also keep youngsters, and older family members happy for a few hours, as well as a pool–most will prefer a heated pool outside of the peak summer months.”
Just as important as planning activities is to plan areas where family members can retreat for a sense of privacy and calm. Look for accommodations that offer private terraces or balconies off of bedrooms, along with a library or sunroom that can act as designated quiet zones.
Choosing a location on the outskirts of a town is a good idea too: larger families will have plenty of space, while also maintaining access to shops and restaurants. “Most multi-gen parties are likely to want to be near enough to a village for one or two of the party to head to make their own entertainment from time to time, or simply to pop out to a boulangerie,” Red Savannah says.
With that advice in mind, here’s a look at a few ideas for where to book a multi-generational vacation:
Multi-Gen Cruise to Alaska
Alaska has become one of the top-requested destinations for multi-generational trips, according to Robyn Jacobs of Orca Travel Agency. It’s not hard to see why. For an outdoorsy adventure with the whole extended family, an Alaska cruise is an ideal option. Families can immerse themselves in awe-inspiring landscapes and see rare wildlife, while having access to a wide array of activities back on board.
When MSC’s newly refurbished ship MSC Poesia debuts in Alaska in May, for example, the vessel will offer a reimagined slate of family programming geared toward multi-generational groups. Families can embark on thrilling excursions like whale watching tours or exploring the ice caves of Mendenhall Glacier while in port. When they return to the ship, they can partake in new entertainment offerings, including game show experiences like Quiz O’Clock and Chart Toppers, a refreshed Lego Family Game Show, and an expanded Naturalists program with enrichment talks, presentations on wildlife, and a dedicated children’s session.
The refurbished Poesia will also offer newly outfitted with MSC’s “ship-within-a-ship” concept, the MSC Yacht Club, which offers 69 spacious suites with access to private amenities and 24-hour butler service, giving older family members a more serene space to relax.
Private Villas in Umbria or Tuscany
Italy is a hard destination to beat for a multi-gen trip, with amazing history, breathtaking landscapes, and of course, its legendary culinary scene. “Italy is incredibly accommodating for families, with children welcomed in many restaurants,” according to Red Savannah.
Italian regions known for spacious villas are a perfect fit for multi-generational groups. “Many villas in Tuscany and Umbria, for example, are converted farmhouses with lots of character, often with separate barns that have been converted into annexes that sit adjacent to a main farmhouse,” Red Savannah says.
Properties with multiple buildings or separate guesthouses are perfect for grandparents who might want more peace and quiet or teenagers who want to be rowdier, according to Red Savannah. They usually have their own entrance but are still connected to the property’s communal amenities like a pool or garden.
An example of an ideal villa for multi-gen groups would be Casale di Fiesole. Located in the Tuscan countryside 30 minutes from Florence, the property offers plenty of space and a peaceful escape with easy access to a wealth of museums, galleries, restaurants, and boutiques.
Residential-Style Resort in the Maldives
The Four Seasons Maldives at Kuda Huraa offers unfettered access to the crystal clear waters and powder-soft shores of the Indian Ocean—a stunning backdrop for a relaxing multi-gen vacation. The top-tier, off-the-grid resort is the perfect place for generations of family members to bond.
In addition to its pristine shore line, the property offers special programming to suit all ages and encourages time together, like private yacht and snorkeling tours, tennis and surfing lessons for all ability levels, and even PADI dive training centers geared toward children, teens, and adults.
Accommodations-wise, the resort offers a three-bedroom estate well-suited to large family groups of up to six adults and three children. The beachfront villa comes with a private pool, full kitchen, dining room, and living room, all framed by sweeping ocean views. It all adds up to the perfect location for an extended family to combine relaxation and once-in-a-lifetime activities.
‘Legacy’ Safaris in Africa
African safaris are an emerging sector of the multi-generational category, and the trend is set to pick up steam in 2026. “We're witnessing the emergence of 'legacy safaris’ [which are] multigenerational groups seeking transformative wildlife encounters that blend meaningful conservation work with solid safari experiences,” according to a report from luxury travel operator Abercrombie & Kent.
“Kenya remains the gold standard, with families now extending stays to include hands-on conservation alongside traditional game drives, creating deeper emotional connections to wildlife preservation.”
The company’s forthcoming safari lodge, Kitirua Plains, an A&K Sanctuary in Kenya’s Amboseli National Park, was designed with family legacy safaris in mind. The lodge opens in June and offers 13 standalone suites (some of which have two bedrooms) set in a 128-acre private concession adjacent to the park with captivating views of Mount Kilimanjaro. The park is an Unesco Biosphere and is known for its large herds of roaming elephants, which families can observe during game drives. Visitors can also visit local Maasai communities and help out in A&K’s work to support healthcare services, education, and more.
Multi-gen groups can also expand their trip to A&K’s two additional Sanctuary properties in Kenya: Olonana in the Maasai Mara, known for its proximity to the Great Migration, and Tambarare Camp in Ol Pejeta Conservancy, home to the last two remaining northern white rhinos on earth.
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