Group cruising fixes the two things that sink group trips: money fights and logistics. Everyone books their own cabin at their own budget, from inside rooms to suites, and the ship does the daily planning. Nobody argues about restaurants when there are fifteen of them. The private-island day is the one to protect; it is the best beach day of the itinerary and the only one where the whole group lands in the same place with nothing scheduled against it.

Two tips from people who run these often: set one standing meetup, dinner together every night is plenty, and let everything else be optional. Forced togetherness is what makes families hate group travel. The ships out of Miami run short three- and four-night formats too, which make a low-commitment first reunion cruise before you attempt the week-long version.