Antigua

Antigua's Heritage Quay in St. John's is a duty-free shopping zone surrounded by a city that has more character than most cruise brochures suggest. The port area is safe and walkable, and the island has 365 beaches — one for every day of the year, as they'll happily tell you approximately 400 times.

Shirley Heights for sunset views, English Harbour for maritime history, and any number of white-sand beaches for pure relaxation. The island is genuinely beautiful and less developed than some of the busier Caribbean ports. The catamaran tours and snorkeling excursions are consistently well-reviewed.

The value proposition is moderate — not as cheap as Mexico, not as expensive as Bermuda. Taxis have fixed rates (posted at the port), and the local food scene is underrated. The rum punch at almost any beach bar is going to be better than what you're getting on the ship, and that's a hill we'll die on.