Hop-On Hop-Off Trolley Tour Key West

Old Town Key West and the trolley route

Old Town is the historic heart of Key West, a compact grid of conch-style houses, shady verandas, tropical gardens and old stone buildings that grew up around the harbour in the nineteenth century. A Key West trolley tour is the easiest way to understand how the island fits together, because the loop passes the main sights in a sensible order and the guide explains what you are looking at.

Many visitors ask whether the Key West hop-on hop-off tour is worth it. On an island this small the answer is yes if you want context rather than just a map: one full circuit without getting off takes roughly an hour and a half, and with stops you can easily fill a day. Tickets are valid on the day of use, and the two-day ticket lets you split the loop over two relaxed days.

Duval Street and Mallory Square

Duval Street runs across the island from the Gulf of Mexico to the Atlantic and is the liveliest street in Key West, lined with galleries, souvenir shops, porch cafes and music venues. Hop off here in the morning for a quiet stroll, or return after dark when the street fills with people. The trolley saves you the long walk back to your hotel at the end of the day.

At the Gulf end sits Mallory Square, the traditional place to watch the sun go down over the water. Evening crowds, street performers and market stalls gather here, and the best time to visit Mallory Square is roughly an hour before sunset so you can find a good spot. Check the sunset time for your travel date, as it moves a lot through the year.

The Hemingway House, the Little White House and the lighthouse

A short distance from Duval Street you reach the house museum where the American novelist Ernest Hemingway lived and wrote in the 1930s, now known for its garden and the polydactyl cats that roam the grounds. Nearby are the Truman Little White House, the winter retreat of a US president, and the Key West Lighthouse, which you can climb for a view over the rooftops.

Entry to these attractions is not included in the trolley ticket, so Hemingway House tickets and lighthouse tickets are bought separately at each site. The trolley still earns its place here, because the stops are close to each gate and the guide's commentary prepares you before you go in.

The Southernmost Point and Fort Zachary Taylor

The big painted buoy at the Southernmost Point is the most photographed landmark in Key West, marking the southern tip of the continental United States and pointing out that Cuba lies about 90 miles away across the water. Most visitors ask how to get to the Southernmost Point from Duval Street; riding the trolley is simpler than walking in the heat, and the stop is clearly signed.

Fort Zachary Taylor, a nineteenth-century fortress now inside a historic state park, sits on the western tip of the island with one of the best beaches in Key West and good snorkelling close to shore. Plan an hour or two here if the weather is fine, then rejoin the trolley for the rest of the loop.

Planning your hop-on hop-off day

Take the first trolley of the day when the streets are quiet and the heat is mild, ride a full loop to get your bearings, then choose three or four places to explore properly. Operating hours change by season, so check the times shown in the booking panel, and remember that the last departure is mid to late afternoon rather than evening.

The best time to visit Key West for pleasant weather is generally the dry season from late autumn to spring, while summer is hotter and more humid with afternoon showers. In either season, bring sunscreen, a hat and water, and wear comfortable shoes for the stops where you hop off.