Best Caribbean Island for a Group Trip

Yeah, you can get a ridiculous house on Tortola for a group like that and schedule boat charters for day trips to other islands.

For the kid's high school graduation, a group of 15 booked a 13,000 square foot oceanfront house with pool in Jamaica. We had 3 cooks, a cleaning lady a laundress, driver and a night time security officer. We stayed a week and split the total cost. It was very affordable considering it included 3 meals a day with servers, constantly stocked bar, daily maid service.

Why it’s best to have 6 people. 3 couples is plenty.

Thanks for all the input. Do you have any information on where this trip was booked? Did someone put all of that together, or was an outfit used to book all of this? And for the group size, realistically it is closer to 10 (5 couples). We have taken groups trips to other places and it worked out fairly well. Everyone understands that not everyone is going to be catered to, but most are good about if they commit to going, they commit to paying (lodging) regardless if they go or not. We were just looking to expand to a Caribbean Island and was looking for recs. Thanks again.

I don't know if its possible for a group of 10, but I'd look into a boat rental if you are going to be doing other things then just renting a house and sitting on the beach. It may be financially reasonable, maybe not. You'd have to like each other for sure, wouldn't want to be stuck on a boat for a week with someone you didn't like lol.

We've done 3 family vacations in the Caribbean. 3 families, total of about 15 people each time. We've done Aruba, St Thomas, and Grand Cayman. Rented a house at each through VRBO.

Which one is best just depends on the group's interests. Of the 3 we went to, St Thomas was my favorite, followed by Aruba. I wasn't all that impressed with Grand Cayman, but it was probably the safest of the 3 if that's important to you. I never felt unsafe in St Thomas or Aruba though, and we got off the beaten path in St Thomas looking for local flavor. St Thomas put us close to the BVI, which the wife and I fell in love with.

St Thomas.

Safe, plenty to do eating, drinking, shopping. Close enough to take a day trip to a couple of BVI if anyone wants. Should keep everyone from getting bored and offer something for everyone.

It wasn't really needed, more of feel good thing for Americans. Rarely even had people walking down the beach.