14 Night Southern Caribbean

Boston is a compact, walkable city with 400 years of American history layered into its streets, parks, and harbor. The Boston cruise port at Flynn Cruiseport (Black Falcon Terminal) sits in South Boston, about 2 miles from downtown and the Freedom Trail.

St. Thomas cruise port is one of the busiest stops on Eastern Caribbean itineraries and the hub of the US Virgin Islands cruise scene. The port handles two main cruise terminals.

St. Lucia is one of the Caribbean's most topographically dramatic islands, defined by the twin volcanic peaks of the Pitons rising sharply from the southwestern coast. The Castries cruise port sits on the island's northwest side, with ships docking at either Pointe Seraphine (a duty-free shopping complex within walking distance of downtown Castries) or the La Place Carenage terminal on the opposite side of the harbor.

You've probably seen photos of Willemstad even if you don't realize it: that row of pastel-colored Dutch colonial buildings along the Handelskade is one of the most photographed waterfronts in the Caribbean. It's been a UNESCO World Heritage Site since 1997.

Aruba's capital sits just 15 miles off the Venezuelan coast, and it's one of the southern Caribbean's most popular cruise stops for good reason. Five berths across three air-conditioned terminals handle up to five ships at once, with water depths of 32 to 36 feet.

Grand Cayman is the largest of the three Cayman Islands, a British Overseas Territory in the western Caribbean known for Seven Mile Beach, exceptional diving, and its role as a major offshore financial center. George Town serves as the cruise port, but there's no pier large enough for cruise ships.