Getting the whole family together is the easy part. Finding a trip everyone wants to take? A little harder.
Different ages. Different interests. Very different ideas of what “vacation” means.
After planning several families luxury multigenerational family vacations (and our own) I’ve learned that where you stay matters just as much as where you go.
Together. Just not all day.
Take a look at some ways we’ve (successfully) planned successful multigenerational family vacations.. and some mistakes we’ve made along the way. For example, when James should have been left on the boat with grandma + grandpa!
1. The Easy: Luxury Resorts – Hawaii, Costa Rica, Caribbean + Disney
Sometimes you just want easy. A great resort provides choices, kids meals and best of all – kids clubs for a luxury multigenerational family vacation.
Visit Four Seasons Hualalai and let the kids loose at King’s Pond or the kids club. Here, the concierge team is outstanding. Must do activities – a manta ray night snorkel, outrigger canoe excursion, a snorkeling and reef-fishing charter, and a convertible rental for driving around the island.
In the Caribbean, Jumby Bay is one of our favorites resorts for multigenerational families. It is a luxury all – inclusive, so no big bill to worry about at the end.
Costa Rica has been a hit – especially the resorts on Peninsula Papagayo. There are three luxury resorts – Four Seasons, Andaz and Ritz Nekajui (we recommend the Ritz for couples as the beach is quite small). The Andaz is increasing their villa and multi-bedroom product and excited to see the results. There is a shared golf course, tennis facility and new waterpark. In addition, The Explorers curates outdoor pursuits and learning opportunities on land and sea.
And don’t forget the obvious one: Four Seasons Resort Orlando at Walt Disney World
Disney can be a fantastic multigenerational trip. The trick is not making every generation do Disney the same way. Stay at Four Seasons Orlando, let the kids enjoy the parks – and you can join when you want.The resort has its own five-acre water park, lazy river, pools, kids club, golf and spa to enjoy after seeing Mickey and Minnie.
We have a Disney lover on our team (guess who)? So don’t forget to reach out to Menzies Luxe Retreats for your Disney trips. Stay tuned, she’s doing her due diligence on the new Disney cruise ships – more on that to come!
WHY IT WORKS: Nobody has to be on the same vacation.
2. The Estate: England, Ireland + Scotland
An estate makes it easy to spread out without really going anywhere.
At Adare Manor in Ireland, home of the 2027 Ryder Cup, parents can golf while the kids try falconry, fishing or archery.
Visit Heckfield Place in England, a great combination trip. Start in London for some sightseeing and enjoy the grounds at Heckfield Place – walk or bike, swim in the lake, explore the farm and gardens or disappear to the spa.
Or, head to Scotland and visit Gleneagles, you have golf, riding, shooting, falconry, tennis and some of the best programming I’ve seen for older kids. For a larger family, look at the Glenmor Lodges at Gleneagles. Having everyone under one roof (+kitchen and laundry) can make a family vacation much more fun and economical.
WHY IT WORKS: Everyone can have a completely different day without really leaving.
3. The Ranch: Montana
Summer at The Ranch at Rock Creek means horseback riding, fly-fishing, hiking, mountain biking and long days outside. Winter might be even more fun. Ski at nearby Discovery Ski Area, snowshoe, skate or sled, then come back to the ranch and warm up by the fire.
Best of all, no one has to figure out where (or what) the family is having for dinner.
WHY IT WORKS: Lots to do. Very little to organize.
4. The Yacht: BVI, Greek Islands, Croatia
This is a very different way to do a luxury multigenerational family vacation. You only unpack once!
Charter a yacht through the British Virgin Islands, Greek Islands, or Croatia. Swim off the back. Head ashore for lunch. Explore a town. Go tubing with the kids. Better yet, catch up on the book you keep opening and never have time to read.
Everyone can do as much, or little as they want. Plus, meals, and activities are all taken care of. Want more action and adventure – try chartering a boat in the Galapagos!
WHY IT WORKS: Your hotel moves with you.
5. The Safari Camp: Kenya + South Africa
Safari is one of those rare trips that works at 7 + 75 and it gives a big family something genuinely memorable to experience together.
In Kenya, head to the Maasai Mara for game drives, learn tracking and traditional skills with a Maasai guide, visit a local community or take a hot-air balloon over the Mara at sunrise. Kids can try beading, guided bush walks and stargazing and learn about all the tiny creatures everyone misses while looking for lions.
End the day with sundowners in the bush and dinner under the stars.
WHY IT WORKS: Wildlife, culture + plenty to keep every generation curious. Take a look at my post on Royal Malewane.
6. The Villa or Residence: Everyone Under One Roof
For some families, this is still the BEST setup, and the one requested most often.
A villa or resort residence gives you space. In Europe, a staffed villa can work beautifully. Provence is one of my favorites because different generations can shop, bike, visit markets, enjoy a cooking class at the villa, or enjoy time spent together at the pool Other villa hotspots – Mallorca, Tuscany and Lake Como.
Many of our favorite resorts also include residences. More space if you want to all be together – with the conveniences and amenities of a hotel.
WHY IT WORKS: Everyone gets their own space, but you still feel like you’re traveling together.
A Few Things I’ve Learned About Multigenerational Travel
Ask the boring questions. How many stairs? Is the pool gated? Where are the bedrooms? Is there AC? Is there a first-floor bedroom? These things suddenly matter a lot when you have a 3-year-old + a 75-year-old under the same roof.
Pick a few things everyone does together. Not ten. One great boat day or dinner is better than a week of forced family fun.
Make meals easy. Get the chef.
Give everyone some independence. The goal isn’t to spend every waking minute together. It’s to still like each other at the end.
My Quick Picks for a Luxury Multigenerational Family Vacation
| If you want… | I’d choose… |
|---|---|
| Easiest overall | Luxury resort |
| Everyone under one roof | Villa |
| Lots for different ages | Country estate |
| Active + very little planning | Luxury ranch |
| Adventure | Safari camp, Costa Rica |
| Beach + total ease | Jumby Bay |
| Disney without doing Disney 24/7 | Four Seasons Orlando |
| Everyone unpacking once | Private yacht |
| Big shared experience | Safari |
FAQs
What is the best multigenerational family vacation?
It depends on the family. For ease, I like Hawaii, the Caribbean or Costa Rica. With a more active family, try a ranch or country estate. Celebrating a milestone – safari or a private yacht is hard to beat.
What type of accommodation is best for a large family?
I often prefer a villa or residence attached to a luxury resort. Space and option to cook breakfast/lunch at home and then head out for dinner is a great plus. Also, you have the amenities of the resort.
How far ahead should you plan a multigenerational vacation?
I’d start 9–12 months ahead, especially if you need several rooms or a villa. We recommend booking a Yacht or safari camp 12+ months ahead, especially during peak seasons like Festive or Summer.
The destination may not sell out, but the right configuration for your luxury multigenerational family vacation often does.
How long should a multigenerational trip be?
Usually 7-10 works well for a luxury multigenerational family vacation.
Why Book Your Multigenerational Trip With Us?
You can book a hotel yourself. But when you’re coordinating multiple rooms and multiple generations, knowing what to book becomes just as important as where. As a Virtuoso Partner agency, our clients booking eligible hotel rates typically receive benefits at no additional booking fee, such as:
- Complimentary breakfast
- Hotel or resort credits
- Priority for upgrades, when available
- Exclusive offers and amenities
- VIP recognition with the hotel team
- Priority for the best available rooms and suites
- Competitive hotel rates, plus the added benefits
But for these luxury multigenerational family vacations, I think the bigger value comes before anyone checks in. Which rooms connect? Should you book four hotel rooms or a residence? Is Grandma going to have to climb three flights of stairs? Is there enough for the teenagers to do? Those little details can make a very big difference when you’re traveling with a big family.
