Best Caribbean Island for a Group Trip

Been to BVI and Grand Cayman. BVI and it’s not remotely close for my tastes.

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.

I can't help you on where to go, but my advice is to be careful because no matter how good of friends you are if its a big enough group there's almost always one couple that cancel and then you need to have a plan for paying for their part.

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.