Key West for first-timers: attractions, museums and tours

How this guide works

Key West packs its museums, historic houses and sunset square into a small Old Town grid, so a first visit is mostly a question of order and getting around, not distance. This guide groups the attractions that already have source-backed KeysCompass pages by area and by the kind of visit, so you can plan a day without crossing the island twice.

Nothing here is ranked, and the order inside each group is geography. Every name links to a KeysCompass page that points back at the operator's own site or the City of Key West. We do not publish admission prices, opening hours, tour start times or phone numbers here, because those change faster than a guide. Open each operator's site the day you go. For the full lists, use the Key West directory links at the end of this guide.

Train, trolley or your own feet

The Conch Tour Train has run open-air sightseeing tours since 1958. Its site describes a narrated 60-minute tour that makes one loop through Old Town, starting at the 303 Front Street Depot and ending right behind it in Mallory Square, with a close-up view of places such as the Truman Little White House and the Key West Aquarium. It is one ride, not hop-on, hop-off. The operator says the train is closed on the last Saturday in October, during Fantasy Fest.

Old Town Trolley Tours, Key West is the hop-on, hop-off option. Its site lists 13 stops, says you can start at any of them, and sells tickets with a day of unlimited reboarding. Pick the trolley if you want to ride between stops and get off for museums; pick the train if you want one narrated loop and then a walk.

Old Town is also easy on foot or by bike. The Oldest House Museum says it is within a 10-minute walk of the cruise port, and the Sunset Celebration organizers say walking or cycling is the easiest way to reach Mallory Square. If you would rather see the town after dark with a guide, read Key West ghost tours: walks, trolleys and Robert the Doll, which compares the night trolley, the walking tour and the firehouse evening.

Mallory Square at sunset

Mallory Square is the City of Key West's waterfront plaza at 400 Wall Street, near the foot of Duval Street. Sunset Celebration takes over the dock and plaza every night, weather permitting. The organizers, the Key West Cultural Preservation Society, say it is free to attend, begins about two hours before sunset, and that the street performers work for tips.

The organizers say walking or cycling in is easiest, because the Mallory Square lot gets congested around sunset. Plan dinner for after the sun goes down, using Where to eat in Key West, by neighborhood.

Whitehead Street: three houses and a lighthouse

Whitehead Street holds several museums within a walk of each other. At the harbor end, Audubon House and Tropical Gardens at 205 Whitehead Street is the 1840s home of Captain John Huling Geiger, a maritime pilot and master wrecker. The museum says the house was slated for destruction in 1958 and that its restoration was the first of its kind in Key West and sparked the island's restoration movement.

Up the street, The Ernest Hemingway Home & Museum is at 907 Whitehead Street. The museum says some of the cats on the grounds descend from a six-toed cat a ship's captain gave Hemingway. A short walk farther along, the Key West Lighthouse & Keeper's Quarters Museum at 938 Whitehead Street is run by the Key West Art & Historical Society. The society says the current lighthouse opened in 1848 with a woman as its keeper, was decommissioned by the Coast Guard in 1969, and that visitors can climb 88 steps to the top of the tower.

The Tennessee Williams Museum is the society's museum for the playwright, who lived in Key West from 1941 until his death in 1983. The society's page says the museum is temporarily closed during its relocation to 604 Whitehead Street, with hours listed as coming soon, so check that page before you plan it into the day.

Duval Street and Elizabeth Street gardens

Oldest House Museum & Gardens at 322 Duval Street is run by the Old Island Restoration Foundation. The foundation says the house was built around 1829 and that its garden holds the oldest surviving cookhouse in Key West. Tickets are sold in the museum store next to the house, reservations are not required, and a self-guided mobile tour comes with every ticket. The foundation also says an ADA-compliant ramp gives access to the house.

A few blocks away, Nancy Forrester's Secret Garden at 518 Elizabeth Street is a parrot sanctuary in a garden, where visitors can talk with orphaned parrots, including macaws. Its website is being rebuilt and still shows older visiting information, so confirm the current details with the garden before you go, and leave your own parrot at home.

The Historic Cemetery and Fort East Martello

The Key West Historic Cemetery is the city-owned cemetery in the middle of Old Town. The City of Key West says it was established in 1847 and covers 19 fenced acres, with the main entrance and the Sexton's office at Angela and Margaret Streets. A free self-guided tour map is available at the front entrance, and guided tours are arranged through the Sexton's office. It is still an active cemetery, so give services room.

Fort East Martello Museum is outside Old Town at 3501 S. Roosevelt Blvd. The Key West Art & Historical Society says the U.S. Army began building the Civil War fort in 1862 and that the society opened it as its first museum in 1950. It is also where Robert the Doll is displayed. Key West ghost tours: walks, trolleys and Robert the Doll has more on Robert and on visiting the cemetery by day.

If it rains

A wet afternoon still works if you stay near the harbor. The Key West rainy-day museums kit on Day kits groups indoor stops by area: Key West Museum of Art and History at the Custom House, the Key West Aquarium, the Key West Shipwreck Museum and the Mel Fisher Maritime Museum at the harbor end, a guided house tour at the Harry S. Truman Little White House or the Hemingway house, and the glass dome at the Key West Butterfly & Nature Conservatory at the Atlantic end of Duval Street.

Audubon House, the Oldest House and the lighthouse all have gardens or outdoor grounds, so bring a rain layer, and save the 88-step lighthouse climb for a dry spell.

Parking, cruise days and planning the day

Old Town parking is mostly metered street spaces and public lots. The Oldest House Museum notes that metered spaces near it are limited, first come, first served, and paid through the Key West Parking app or nearby kiosks. If you are arriving by ship or only have a few hours, read Key West parking and cruise day: pier, Old Town and honest timing first.

A workable first day is one ride, a short list of houses or museums on one end of Old Town, and Mallory Square at sunset, with dinner after. Save your picks and a rain backup on the Trip planner, and re-open each operator's site the morning you go for hours, tickets and any closures.

Frequently asked questions