The Port of Key West is a port in Key West, Florida.It includes Key West Bight, Garrison Bight at City Marina, as well as three docks that could be utilized by cruise ships.

The first cruise ship to adopt the port was the Sunward in 1969. It docked at Pier B, which was owned at that time by the U.S. Navy.

In 1984, the city opened a cruise terminal at Mallory Square. The decision was met with opponents who claimed that it would disrupt the tradition of watching the sunset at Mallory Square.

In 2013, a referendum to widen the ship channel was defeated by 73% of voters. The proposal, backed by the Key West Chamber of Commerce, was intended to accommodate larger cruise ships and would have required dredging 17 acres of sea bottom, which includes endangered corals, in the protected Florida Keys National Marine Sanctuary.

In 2020, Key West voters approved three amendments to the City Charter which prohibit large cruise ships, limit daily disembarkations, and prioritize cruise ships with superior public health and environmental records. The amendments, sponsored by the Key West Committee for Safer, Cleaner Ships, passed with 61% to 81% approval. However, the following year, the state legislature overturned the amendments. In 2022, the city decided to instead prohibit ships from docking at the two piers the city controls. Meanwhile, Pier B is planned to undergo an expansion renovation to service bigger ships, which would first have to be approved by the state.