Old Town Trolley Tour in Key West: the Fun Hop-on-Hop-off Way around Town

You can’t go wrong with one of the trolley tours in Key West, and Old Town Trolley is a good option for both getting the historic scoop on the town or enjoying some hop-on-hop-off transportation all around the island. And before you ask, yes, the Old Town Trolley Tour of Key West is different from the Conch Train Tour or Ghosts and Gravestones. This one is all about the history, both stories and architecture, vs being about the quirkiness of Key West.

Let me explain a bit more as you read on and you’ll see why this is one of the most popular things to do in the Florida Keys. If you have any questions about Key West’s Old Town Trolley Tour or need some additional recommendations for things to do when you’re here, please leave a comment or send us a note. We’re always happy to share more and help you plan a wonderful trip to the Florida Keys.

Highlights of the Key West Old Town Trolley

Since Key West has three different trolley tours, it might seem like any of them are interchangeable, but they’re actually each quite different. The Old Town Trolley is great for getting the basic history of Key West and hearing about the architecture of many of the buildings. The storytelling is simple and direct with a few funny bits thrown in, whereas the Conch Train Tour really leans into the humor and quirks of Key West, and then Ghosts and Gravestones is a mix of history and creepy urban legends of town.

I think the reason I enjoy the Key West Old Town Trolley tour is because it’s much more facts and less audience participation than the other tours. For a lot of Key West visitors they also like using the Old Town Trolley tour for the hop-on-hop-off aspect. With around 20 stops on the route (very quick stops though) there are lots of chances to be able to get off the trolley in different parts of town, and likewise you can walk around a bit and if you’ve got a trolley tour ticket/sticker, you can just back on and continue the tour. The flexibility it offers makes it easy to explore Key West both on foot and via the trolley. Want to stop at the Key West Lighthouse or Hemingway Home? No problem. Have a snorkeling tour going out of the Historic Seaport? Get off there and later you can ride back on the trolley (timing permitting).

Now, this may sound odd, but doing the Old Town Trolley in Key West is actually a great way to spend time together when you’re in town with a big family, like visiting with grandparents or another family. You can do the tour together, but then also get off where you would like to and the rest of the party can continue on or just return to the depot, returning them to somewhere familiar so they don’t get lost. It’s just so easy to use it as both a means of transportation and a source of entertainment.

Get Old Town Trolley Key West tickets here!

Tips for Using Old Town Trolley in Key West

Considering that you’ll have access to the Old Town Trolley tour all day long, you might as well start your day of sightseeing with it. You can hop on and off all day long, so if there’s a part of town you’re most interested to hear about, do your walkabout and then find one of the Trolley Stop signs and wait for the next one to come around, which is usually every fifteen minutes or so. There are lots of tours running all day, so it’s not difficult to get on one as they go by.

Key West is a warm city, whether you’re visiting the Florida Keys in summertime or if you’re here in the winter months. It’s nice to have some sun protection since it’s an open-air experience. Yes, the Old Town Trolley tour is covered, but you’re still getting a lot of sun as you ride around town. And then if you choose to get off at the beach or the Historic Seaport or something, you’re going to want to be sun-blocked up before then.

It’s a good idea to look at the maps of trolley stops before you start your tour just in case you want to get off somewhere. You can also ride the whole route and then stay on until you get back to the stop you wanted. When you buy your Old Town Trolley tickets you’re given a sticker to show you have paid for passage, so you can continue to hop on and hop of throughout the day. There’s lots of ways to make the tour/transportation work well for your trip.

Being Prepared for an Old Town Trolley Tour

There really isn’t a lot to consider when you’re planning to do the Key West Old Town Trolley Tour. Because it’s a hop on and hop off tour, you can join it at the Mallory Square depot and then get off to walk around wherever you like. If it’s too hot, jump off the trolley and head into a museum. If you wanted to hear more of the history or you weren’t paying attention earlier on your guided tour, you can get back on and do the loop or part of the route again. It’s great to be able to fly by the seat of your pants and enjoy the Old Town Trolley Tour as best suits you.

I will say, you should wear sunscreen when you’re planning a day of using the Old Town Trolley Tour. While you may get an initial seat in the shade, as the trolley moves through Key West, the suns shifts and you may get a lot of sun exposure. We recommend dressing with sun shirts or using sunblock (reef safe if you’re swimming later) before heading out for the day. If you’re concerned about rain, there are windows that come down on the trolley, but Old Town Trolley Tours also provides plastic ponchos if needed. They make i t easy to enjoy the tour and the option of walking about town.

Having a camera with you on the Old Town Trolley Tour in Key West is a good idea. While photography from a moving vehicle is tricky and you don’t always get the best photos, you can always get off at the different stops and walk around taking pictures. There’s usually another trolley in fifteen minutes, so instead of getting poor quality pictures, actually get off the tour and use your camera to capture the cool architecture and beautiful sights of Key West.

Parking for Old Town Trolley Tours

There is parking in some different small lots around Mallory Square, but parking is tight and expensive. If you’re staying in the Historic District or along the water downtown, just walk to the trolley depot. If you’re staying on Roosevelt Blvd or another more far-out place (such as the Perry Hotel on Stock Island) plan on using your resort’s provided transportation or get an Uber to downtown. Parking in Key West really is a pain and you’ll be much happier if you don’t have to deal with it.