Getting the whole family in one place is harder than it sounds. There are school calendars to navigate, work diaries to compare and, before long, a WhatsApp group with far too many opinions on where everyone should go. Which is exactly why, when a multigenerational holiday does come together, it matters.
Travelling with grandparents, parents, children and sometimes a few cousins too gives you something everyday life rarely does: real time together. Breakfasts that turn into long lunches. Grandparents taking the little ones for an afternoon. Teenagers disappearing to do their own thing, then resurfacing for dinner. Everyone sharing the same trip, without needing to spend every waking hour together.
The trick is choosing somewhere that works for different ages, interests and energy levels. Our luxury family holidays are designed with exactly that balance in mind, with enough shared experiences to bring everyone together and enough space to occasionally go your separate ways. Here are five destinations that do multigenerational travel particularly well.
Singapore
Singapore is one of those places where nobody has to compromise too much. For younger travellers, there is Universal Studios Singapore, Singapore Oceanarium and the wildlife parks. For adults, there are rooftop bars, excellent restaurants and some very good shopping. And for everyone in between, Gardens by the Bay, river cruises and the city’s hawker centres make it easy to experience Singapore together.
Food is another great equaliser here. Singapore can take you from chicken rice and chilli crab at a hawker centre to Michelin recognised dining in the space of a day, so even a family with wildly different tastes is unlikely to struggle.
Stay at Shangri La Hotel Singapore
Shangri La Singapore is a natural fit for families who want the energy of the city without feeling as though they are staying in the middle of it.
Children have plenty of space to play, including a dedicated indoor play area and Splash, the hotel’s 1,300 square metre outdoor water playground. There are also themed family suites for younger guests, while adults can retreat to calmer corners of the hotel when required.
It is that ability to give everyone their own version of the holiday that makes it work particularly well for larger family groups.
Oman
For families who want winter sunshine but would like a little more than a week beside the pool, Oman makes a compelling case. There is culture in Muscat, mountains inland and wadis cutting through the landscape. You can snorkel around the Daymaniyat Islands, explore traditional souqs, head into the desert or simply slow things down beside the sea.
Oman is also a destination that lends itself to travelling at a slower speed if you need to. That can make a real difference when grandparents and young children are part of the same trip. The cooler winter months are particularly appealing for family travel, while southern Oman takes on a very different character during the Khareef season - a monsoon period that changes the landscape to a lush, mist-shrouded green - between June and September.
Stay at Al Bustan Palace, a Ritz Carlton Hotel
Set between the Al Hajar Mountains and the Sea of Oman, Al Bustan Palace gives families plenty of reasons not to rush anywhere. There is a kilometre long private beach, several outdoor pools and Ritz Kids activities covering everything from crafts to cooking. Younger guests have plenty to occupy them, while adults can make the most of the spa, beach and slower pace. Its location also means Muscat is close enough for days out, without the hotel itself feeling overly urban.
For another family focused option in Oman, Shangri La Barr Al Jissah Resort Al Waha has a lazy river, splash areas and dedicated children’s activities, making it particularly good when younger children are leading the holiday agenda.
Costa Rica
Some family holidays are about switching off. Costa Rica is more about switching everyone on. Sloths hanging above forest trails, toucans in the trees, turtles along the coast and monkeys providing an unexpectedly effective early morning alarm call. Nature has a habit of doing the entertaining here. That makes Costa Rica especially good for families with older children and teenagers, although itineraries can easily be adapted for younger travellers and grandparents too. Guided wildlife walks can be gentle, river journeys can be calm and volcanic hot springs offer a welcome change of pace after more active days.
It also gives families something increasingly valuable: shared firsts. Seeing a sloth in the wild for the first time tends to level the playing field, whether you are eight or 78.
Stay at Nayara Tented Camp
Close to Arenal Volcano National Park, Nayara Tented Camp puts you right among Costa Rica’s rainforest without asking you to rough it. Beautiful, tented accommodation that float among the trees, private plunge pools and larger configurations give families room to spread out, while wildlife, hot springs and nature experiences are all close at hand.
For multigenerational groups, that combination works particularly well. There is enough adventure to keep younger travellers engaged, but the setting means slower days can be every bit as rewarding. Families planning a bigger trip may also want to explore our guide to the best family holidays to take in your lifetime, particularly if you are looking for something that feels like a genuine once in a lifetime experience.
The Algarve
Sometimes the easiest family holiday is the best one. The Algarve has long understood how to make travelling with several generations feel straightforward. There are sandy beaches and calm coves for younger children, golf courses for anyone who wants an early tee time, coastal restaurants and walking and cycling around the Monchique Mountains when somebody decides they have had enough of the sun lounger.
It is also easy to build different rhythms into the same day. Grandparents might linger over breakfast while the children head for the pool. Some of the family can play golf while others go to the beach. Everyone meets again later over grilled fish and a bottle of something cold.
Accommodation matters here, particularly for bigger groups. Villas and residences can give families shared living space without sacrificing privacy, while still keeping hotel facilities close by. Our article on family hotels with villa facilities explores some of the best options for getting that balance right.
Stay at Pine Cliffs Resort
Pine Cliffs has been welcoming families to the Algarve for years, and it shows. There is plenty going on for younger guests, including pools, playgrounds, family activities and mini golf, while adults have golf, wellness and the coastline on their doorstep.
More importantly for multigenerational groups, there is a broad choice of accommodation. Families can choose the set up that suits them rather than trying to squeeze several generations into a conventional hotel room arrangement.
The UK
A multigenerational holiday does not necessarily need passports. For milestone birthdays, anniversaries, family reunions or simply a long overdue weekend together, staying in the UK can remove a surprising amount of friction. There are no airports to negotiate, travel times can be shorter and it is easier for different branches of the family to arrive independently.
It also opens up some excellent options. A Scottish country hotel can give golfers, spa lovers and younger children completely different days before everyone meets for dinner. A country house can become your own base for a few nights. London works particularly well when adult children are joining the trip, with restaurants, theatre, shopping and sightseeing allowing everyone to dip in and out of the family itinerary.
Our luxury UK holidays include everything from city stays to countryside retreats, while our guide to UK family staycations gives you the ultimate inspiration to guarantee the kids get outdoors.
Stay at Fairmont St Andrews
Scotland works particularly well when different generations want different things from their time away. At Fairmont St. Andrews, golfers can head for the course, adults can disappear to the spa and younger family members have activities of their own. Larger accommodation options also make it easier to keep everyone together without feeling crowded.
Then there is the setting itself. Coastal walks, fresh air and plenty of room to slow down make a welcome change from trying to coordinate a family gathering around somebody’s dining table at home.
How to make a multigenerational holiday work
The best multigenerational trips are rarely the ones with the fullest itinerary. Start with space: Interconnecting rooms, multi bedroom suites, residences and villas can make an enormous difference, particularly when young children have early bedtimes or grandparents appreciate a little more privacy.
Then think about pace. One shared experience a day is often enough. A boat trip, wildlife drive, cooking class or long lunch gives everyone a focal point without turning the holiday into a timetable.
Accessibility matters too. Shorter transfers, easy access to restaurants, lifts, walkable resorts and the option of private transport may not sound like the glamorous part of holiday planning, but they can be the details that make the entire trip feel effortless.
And finally, do not assume everyone wants the same holiday simply because they are travelling together. The best resorts give teenagers some independence, children somewhere to play and adults enough space to switch off.
If your children are now very much adults themselves, our guide to when family travel grows up looks at how family holidays change once kids clubs and early bedtimes are firmly behind you.
Multigenerational holiday FAQs
What is a multigenerational holiday?
A multigenerational holiday usually brings together three or more generations of the same family, often grandparents, parents and children. Some trips are larger, with siblings, cousins and extended family joining too.
Where is best for a multigenerational holiday?
The right destination depends on who is travelling. Singapore is excellent for variety and straightforward city logistics, Oman combines winter sunshine with culture, Costa Rica suits adventurous families, the Algarve makes relaxed European family travel easy, and the UK is particularly convenient for shorter celebrations and family gatherings.
What type of accommodation is best for a large family holiday?
Villas, residences, interconnecting rooms and multi bedroom suites tend to work best because they combine shared space with privacy. For larger groups, we often look for accommodation that gives families somewhere to spend time together without requiring everyone to follow the same routine.
How far in advance should we book a multigenerational holiday?
Earlier is usually better, particularly if you need several rooms, interconnecting accommodation or a large villa during school holidays. The most flexible family accommodation is often limited, so planning ahead gives you far more choice.
How do you keep different generations happy on the same holiday?
Avoid planning every hour together. Choose one or two experiences everyone is excited about, then leave room for different generations to follow their own interests. Resorts with several restaurants, children’s programmes, spas, sports and easy excursions make this much simpler.
Are multigenerational holidays suitable for grandparents with limited mobility?
Absolutely, but the destination and hotel need to be chosen carefully. We can consider walking distances, room locations, accessibility, transfer times and the physical demands of excursions before recommending a hotel or itinerary.
Can Winged Boots organise activities for different members of the family?
Yes. Your Personal Travel Manager and our concierge team can help coordinate experiences around different interests and ages, from restaurant reservations and private guides to children’s activities, golf, spa appointments and family excursions.
A week together can create the kind of memories that rarely happen at home because everyone is normally heading in different directions. Children get proper time with grandparents. Adult siblings reconnect outside the usual Christmas or birthday routine. And parents occasionally discover the unexpected luxury of somebody else volunteering to supervise the swimming pool. Speak to a Winged Boots Personal Travel Manager today to start planning. You bring the family, we'll handle the moving parts.
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