Key West lies at the tail end of the Florida Keys, the last island on a chain connected by a single highway crossing open water. It is the southernmost point in the continental United States, ninety miles (about one hundred forty-five kilometers) from Cuba, and the small island has built its identity around the geography. Painted wooden houses lean over narrow streets, butterflies live in a glass conservatory off the main road, sunset crowds gather at Mallory Square, and the touristy main strip somehow does not feel manufactured.
Crew like the port because it is easy. The ship docks close to the historic center, the island is small enough that you never need a taxi, and the American supermarkets and chain shops crew familiar with US ports already know are around the corner. For people coming off Caribbean ports where the gangway opens onto a souvenir maze, Key West is the inversion. The town has tourists, plenty of them, but it has not flattened into the tourist version of itself.
On the Ground
On the ground, Key West covers about five square miles. The cruise terminal is close to Old Town, and the walk from the gangway into the heart of the island takes ten minutes at most. For a single port day walking is the natural pace, and the island rewards slow walking more than speed. Bikes and scooters are available if you want to cover more ground, but few crew bother for a one day stop.
WiFi and coffee are easy along and just off Duval Street. Plenty of cafés have stable connections, and the larger chain coffee shops in town are a fallback if you want something predictable. Crew who need to call home or send a stack of backed up messages from the last sea days will not have to search.
Phone coverage is solid if you already have a US SIM from earlier in the itinerary. Crew on European or Asian plans should know that US roaming charges add up on a single port day, so the island is small enough that running on café WiFi for the afternoon is a reasonable plan.
The supermarkets are American chain stores, which means snacks, toiletries, electronics, basic pharmacy items, and most of the small things crew run out of on a long contract. Prices are higher than on mainland Florida but not by a dramatic margin. If you need something specific and the ship’s slop chest does not stock it, you will probably find it within a short walk.
Restaurants and bars on Duval Street charge tourist prices. Move one or two blocks off the main strip and both the prices and the crowd density drop. The food on the side streets is similar quality, occasionally better.
The weather is the variable that catches crew out. Key West is subtropical and the sun is direct. A morning that starts comfortable can become punishing by early afternoon, so carry water and dress light. Plan the shaded indoor sights for the middle of the day if you are out for long.
Getting back to the ship is straightforward because everything is walkable. The terminal is visible from much of Old Town, and the gangway is a short walk from wherever you happen to be. Build a buffer for the last hour anyway, Duval Street in late afternoon can slow you down if the bars are spilling onto the pavement.
Worth Seeing with Time
Worth seeing with time on your hands, the residential blocks of Old Town are the best free attraction on the island. Painted wooden houses in pastel colors surrounded by tropical plants, no entry fee, no schedule, no queue, no obligation. Wander a few streets back from Duval and the character of the place shows itself.
The island’s eccentricity has historical roots. In 1982 Key West responded to a federal border patrol roadblock by declaring itself the Conch Republic. The independence lasted about a minute before surrender, and the new republic then applied for foreign aid. The flag still turns up on T-shirts and restaurant menus, and the spirit of mild absurdity defines a lot of the local culture.
The Butterfly and Nature Conservatory. A climate controlled tropical habitat with hundreds of free flying butterflies and exotic birds, built inside a glass structure surrounded by gardens. Worth the entry fee even if wildlife does not usually interest you. The walk through is one of the more pleasant indoor hours on the island, especially on a hot afternoon when you need somewhere cool.
The Southernmost Point. A large concrete buoy painted red, yellow and black at the corner of Whitehead and South Streets, marking the southernmost tip of the continental United States, ninety miles to Cuba. First time visitors take the photograph, repeat visitors walk past.
Mallory Square. On the waterfront at the northwest end of the island. The Sunset Celebration there is a nightly gathering of street performers, food vendors, art stalls and spectators that has been a Key West institution for decades. Whether you catch it depends on the ship’s sailing schedule. If you are in port late enough to see the sun drop over the Gulf, it is worth the walk.
Ernest Hemingway House. Hemingway lived and wrote in Key West through the 1930s, producing a chunk of his life’s work in the Spanish Colonial house on Whitehead Street. Significant short stories and one of his stronger novels came out of the years he spent here. The house is a National Historic Landmark and still home to dozens of polydactyl cats descended from one Hemingway owned. The polydactyl trait gives them extra toes and has been bred true through generations. Guided tours operate throughout the day. For anyone with even passing interest in American literature, or in the character of the house itself, this is one of the better paid attractions on the island.
Key West City Cemetery. A working historical site with above ground tombs, elaborate monuments and gravestones reflecting the island’s offbeat humor. One is famously inscribed with “I told you I was sick.” Free to walk through. Quieter than the Duval Street strip and tells you something about Key West that the tourist version of the island does not. Half an hour spent walking through it is one of the stranger and cheaper ways to use port time here.
Key West Aquarium. One of the oldest attractions on the island, open since 1934. Home to marine life from the surrounding Florida Keys waters and small enough to cover in an hour. A reasonable backup if the weather turns and you want somewhere air conditioned.
Key West Lighthouse. A working lighthouse built in 1848, now run as a museum. You can climb to the top for views over the island, and the keeper’s quarters next door have been preserved as part of the visit. On Whitehead Street, a short walk from the Hemingway house.
Fort Zachary Taylor State Historic Park. A Civil War era fort at the southwestern tip of the island, surrounded by what is probably the best natural beach on Key West. Construction lasted from 1845 to 1866, and the fort saw use through the Spanish American War. It is open for tours, with interpretation about its role in the Union blockade of the Confederate coast. The beach is less crowded than the more central Key West beaches because of the park entry fee, and the swimming is decent if you want time in the water without the commercial beach scene.
Five square miles, painted wooden houses, the end of the road, ninety miles to Cuba. Some ports do the work for you.
