How to Vacation With 23 Family Members and Still Like Each Other

The answer? Three yachts.

For one recent charter, 23 members of the same extended family wanted to vacation together. The group consisted of a number of siblings, their partners and their children, so while this was very much a big family affair, there were just two generations traveling together.

One yacht simply couldn’t accommodate them all, so instead, they took three. Gullwing, Seahome 2 and Justified Horizons became home for the week, allowing the family to enjoy one vacation together while still having their own space.

And actually, that might be one of the best ways to do a big family vacation. Because you love your brother, but do you really want to hear him snoring in the cabin next door for seven nights? Thought so. Get him his own yacht.

Together, Without Being on Top of Each Other

The beauty of a multi-yacht charter isn’t simply that it allows you to accommodate a much larger group. It allows you to do it comfortably.

In this case, the family was divided across three yachts, with siblings, partners and children spread between them. Each smaller family group had their own home base, their own crew and somewhere to retreat to at the end of the day, while the rest of the family was never far away.

That separation turned out to be one of the things the guests really appreciated. Anna, Chef from Gullwing, explained that everyone enjoyed having somewhere to retreat when they wanted a little downtime from the larger group. They could spend the day together, then head back to their own yacht when they were ready for some space.

It’s something worth thinking about when planning any group charter. Who you vacation with matters, but having enough space from them can matter just as much. We talk more about that in our guide to what matters more than the yacht on a yacht charter.

A multi-yacht charter meant this family didn’t have to choose between a big family vacation and the privacy of a luxury yacht charter. They could have both.

Three Yachts, One Vacation

Having three yachts didn’t mean having three separate vacations. The crews of Gullwing, Seahome 2 and Justified Horizons worked together throughout the charter to make the experience feel connected.

One of the nicest examples was cocktail hour, which rotated between the three yachts each evening. Whichever yacht was hosting would welcome the whole group, while the chefs from all three boats prepared snacks and crew from the other yachts joined the host boat to help serve drinks.

The yachts could also raft alongside one another, creating a much larger social space and making it easy for the group to spend time together. It meant the family could enjoy the privacy of their respective yachts without losing the feeling that they were all on the same vacation.

More Yachts, More Ways to Spend the Day

There was another fairly obvious perk to having three yachts at their disposal: three yachts’ worth of watersports and activities.

With equipment available across the fleet, the family could naturally break into smaller groups throughout the day depending on what everyone felt like doing. Some could head out on the water while others relaxed onboard, and the adults and kids didn’t necessarily need to follow exactly the same schedule.

That freedom is one of the reasons a tandem or multi-yacht charter can work particularly well for a large family. Twenty-three people rarely want to do exactly the same thing at exactly the same time. With multiple yachts, they don’t have to. Everyone can go off and enjoy their day, knowing there will be plenty of opportunities for the whole group to come back together later.

What Happens at Mealtimes?

Food is a huge part of any crewed yacht charter, so naturally there’s another layer of planning when one family is spread across three yachts with three different chefs.

For most meals, the guests ate aboard their respective yachts. There were some more complex dietary requirements within the family, so this allowed each chef to cater specifically to the guests they had onboard. The three chefs also spoke about their menus and loosely planned to prepare similar things, helping to keep the dining experience consistent across the group while still allowing each chef to cater to their individual guests.

The family did, however, choose to eat ashore together a few times during the charter. This gave all 23 guests the chance to sit around the same table, rather than every meal being divided between the three yachts.

And one of those occasions became the highlight of the entire trip.

Dinner for 23 on the Beach

For the family’s bonfire night, all three yachts came together for a special dinner ashore. A dining table was set on the beach for all 23 family members, while the combined nine-person crew from Gullwing, Seahome 2 and Justified Horizons served dinner and drinks.

Anna described the bonfire dinner as the highlight of the charter, and it’s probably the perfect example of what makes a multi-yacht vacation work so well.

The family didn’t need to be together every minute for the vacation to feel like a family trip. They could have breakfast aboard their own yachts, spend the day in smaller groups, retreat to their respective boats when they wanted some downtime, and then come back together for moments like this.

There’s something pretty special about having 23 members of the same family around one table on a Caribbean beach, knowing you can all head back to your own yachts afterwards.

How Do Nine Crew Actually Coordinate?

From the guests’ perspective, the experience should feel seamless. Behind the scenes, of course, there’s a little more going on.

Before this charter began, the crews met to discuss the trip and created group chats so they could stay in communication throughout the week. The captains coordinated the yachts and itineraries, the chefs discussed menus, and the deck/stews worked together on cocktail hours, watersports, games and the occasions when the entire family would be together.

In this case, the crews already knew each other, which made the collaboration particularly easy. Anna said she had actually expected a three-yacht charter to be quite stressful from the crew’s perspective, but found it much easier than anticipated.

That behind-the-scenes relationship between the yachts is an important part of getting a multi-yacht charter right. Guests shouldn’t feel as though they’re responsible for coordinating three separate vacations. With the right yachts and crews, it should simply feel like one.

Choosing the Right Yachts Matters

Of course, a successful charter isn’t simply a matter of finding three available yachts with enough cabins. The yachts need to suit the individual families staying aboard them while also working well together as a group.

Cabin arrangements, crew personalities, watersports and social spaces all matter. Even practical considerations, such as whether the yachts can comfortably raft alongside one another, can make a difference to how easily everyone can come together throughout the charter.

The type of yacht can change the experience too. For some groups, the space and social areas of a power catamaran are ideal, while others may prefer the style of cruising offered by a motor yacht. Our guide to power catamarans vs. motor yachts explains some of the differences if you’re deciding which experience would suit your group.

When you’re chartering multiple yachts, however, it isn’t only about finding the right yacht. It’s about finding yachts and crews that work well together, which is where having an experienced charter broker becomes particularly valuable.

One Family, Three Yachts

Ultimately, this charter proved that splitting a group across multiple yachts doesn’t mean splitting up the vacation. If anything, it gave this family more freedom to enjoy their time together.

They could spend their days however they wanted, come together for cocktails, watersports and dinners ashore, and still have their own yacht to return to at the end of it all.

Perhaps that’s the secret to vacationing with 23 members of your family: you don’t need to spend less time together. You just need somewhere to escape to afterwards.

Bring the Whole Family. Just Don’t Put Them on the Same Yacht.

Family vacations are better when everyone’s invited. They’re even better when everyone has their own space.

With a multi-yacht charter, you can spend the days exploring together, meet up for cocktails and dinners, and still retreat to your own yacht when family time has officially reached its limit.

So bring your siblings. Bring their partners. Bring the kids.

Ready to get the family together? Let’s find your fleet.