British Virgin Islands Okay, so it’s not just one island — but the archipelago is one of the best places for a summer vacation in the Caribbean, thanks to its cool breezes and island-hopping pedigree. You can take a boat through the islands on a Marine Max vacation, stay at one of a host of private-island retreats that will have you and your family covered, or visit the Caribbean’s best hotel for watersports, the lovely Bitter End Yacht Club. British Virgin Islands Hotels to Check Out: Peter Island Resort, Bitter End Yacht Club, Cooper Island Beach Club.