Key West

Key West is the cruise port that locals wish would go away — and they've literally voted on it multiple times. The tiny island gets overwhelmed when large cruise ships dock, and the 2020 referendum to limit ship sizes shows how contentious the relationship has become.

That said, Key West is fantastic for a port day. Duval Street is a straight shot from the cruise pier, Mallory Square sunset celebrations are iconic, and the whole island is walkable. No need for taxis, tours, or excursions unless you want to snorkel or visit the Dry Tortugas.

Here's what the cruise lines won't tell you: Key West has been fighting to limit cruise ship visits, and some of the largest ships have been diverted to other ports. The island's charm depends on it not being overrun, so enjoy it while the balance still works. Also — everything here is priced for tourists, especially on Duval Street. Walk two blocks off the main drag for better food at half the price.