Taking Old Town Trolley Tours in Key West turned out to be one of the best decisions Danielle and I made on our trip. We were staying at a hotel on the northern end of the island, and being able to hop aboard from our hotel made the whole experience easy from the start. We got a tour around the island, learned a ton of history along the way, and had the freedom to get off and explore whenever we wanted.
If you are heading to Key West and wondering whether the trolley is worth doing, my answer is absolutely. For us, it was one of those can’t-miss experiences: practical enough to help us get around, but interesting enough to be an adventure in its own right.
Starting at our hotel made a big difference
Our hotel was away from the heart of Old Town, so the ability to start there was a big part of why this worked so well for us. We could settle into the trolley and start enjoying the island instead of making a separate trip downtown just to begin the tour.
I would check the route against your hotel before booking. Our pickup was convenient, but that does not mean every hotel has a trolley stop. The current route includes several hotel stops, and finding the one that works for your stay is a good first step.
Hop off, explore, and catch the next trolley
The flexibility is what makes this tour such a great idea. You can enjoy the ride and listen to the narration, then get off at a designated stop when you want a closer look at an area. When you are ready to continue, you catch the next available trolley and carry on around the route.
According to Old Town Trolley’s official tour page, the one-day ticket allows unlimited reboarding during the operating day, and you can start at any designated stop. The full ride takes about 90 minutes if you stay aboard throughout. That is the loop time; exploring between rides makes it a longer outing.
That combination suited us perfectly. We could see how the different parts of Key West connect while still having the option to spend more time somewhere that caught our attention. I would especially recommend it early in a trip, when you are deciding which places you want to come back to.
The history was a highlight
This is much more than transportation between attractions. We heard stories about the island as we rode, and those details made the places passing by feel more interesting. Key West has so much history packed into its streets, and having someone point it out added a lot to the experience.
Our tour highlighted the Truman Little White House and Hemingway’s house, along with places connected to Jimmy Buffett—where he lived and places he played. Those were some of the details that stood out to me. They connect the island’s famous names to actual places instead of leaving them as stories you have heard somewhere before.
For anyone who wants to explore beyond the ride, the operator’s official FAQ recommends the Whitehead and Petronia stop for the Hemingway Home, and the Presidential Gates stop for the Truman Little White House. Seeing a landmark from the tour and visiting inside are different experiences, so check the attraction’s admission and the exact ticket package you choose.
How many stops are there, and where are they?
Old Town Trolley advertises 13 stops. Its current official route map numbers the main stops 1–13 and also labels the Truman Annex pickup 1a. That extra label explains why the map has another entry alongside the advertised count.
| Stop | Location | Where to find it |
|---|---|---|
| 1 | Mallory Square | 401 Wall Street |
| 1a | Truman Little White House / Truman Annex | Whitehead Street at Caroline; Presidential Gates |
| 2 | Historic Waterfront / Mac’s Sea Garden | 208 Margaret Street |
| 3 | Simonton & Greene Streets | 190 Simonton Street |
| 4 | Duval Street / La Concha Hotel | Duval Street near Fleming |
| 5 | Bahama Village Market | Whitehead and Petronia |
| 6 | Fairfield Inn | 2400 North Roosevelt Boulevard |
| 7 | Roosevelt Station at Gates Hotel | 3840 North Roosevelt Boulevard |
| 8 | Hampton Inn | 3755 South Roosevelt Boulevard |
| 9 | East Martello Fort / Robert the Doll | 3501 South Roosevelt Boulevard |
| 10 | Casa Marina Resort & Beach House | 1500 Reynolds Street |
| 11 | Butterfly Conservatory / Southernmost stop | 1316 Duval Street |
| 12 | Truval Village | Duval Street near Truman |
| 13 | Angela Street Depot | 451 Angela Street |
Stop names and locations above were checked against the operator’s map on October 7, 2026. Use the live map for boarding directions and any route changes on your travel day.
A few tips for planning your ride
Give yourself time between stops. The operator’s FAQ describes typical trolley arrivals every 20–30 minutes. I would allow some breathing room rather than trying to fit a tightly timed itinerary around each pickup. Their live trolley tracker can help you see where the vehicles are.
Check the last departure for your stop. The published schedule currently starts at 9 a.m., with the last departure from Mallory Square at 4:30 p.m. That is not a promise of a 4:30 pickup at every hotel. Confirm your return plan and current operating hours before you hop off late in the day.
Bring what you need for an open-air ride. My suggestion is to take water, sunglasses, and sun protection, and keep your phone or camera handy. Our photos caught everything from the Mile 0 sign and colorful streets to historic buildings and palms along the route.
Leave room for a favorite stop. The trolley stops directly in front of the Key West Butterfly & Nature Conservatory, another experience Danielle and I loved. You can also read about our visit to Captain Tony’s Saloon as you put together your own Key West list.
Our photos from the trolley tour
Here are a few of the views we captured along the way, from the Mile 0 sign and Casa Marina to the historic buildings around Mallory Square. Part of the fun was seeing what came into view between the major landmarks.
A quick look from aboard the trolley
Would I recommend Old Town Trolley Tours in Key West?
Without hesitation. Starting from our hotel, touring around the island, hearing the history, and having the freedom to get off and explore made this such a good choice for us. The trolley helped us see more of Key West and gave us a better feel for the places we were passing.
I would put it high on the list for anyone visiting the island, especially if you want an easy introduction to Key West without giving up the freedom to explore at your own pace. This is one of those experiences I am glad we made time for.
For current tickets, hours, and route information, visit Old Town Trolley Tours Key West. Follow more of our island adventures in the Adventures logbook and our Key West Dream.
