Between the Walt Disney World Resort theme parks and world class beaches, it's no surprise that Florida is one of the most visited states in America. The Sunshine State, as it has become known due to its wonderful year-long weather, is home to some of the most beautiful scenery and exciting attractions in all of North America, and no visit to Florida can be complete without a trip down to Key West.


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Located in Monroe County in the southern part of Florida, this city is situated at the very end of US Route 1. It's the southernmost city in the contiguous United States and is an unmissable part of any Florida vacation. A beautiful city with a vibrant Old Town area and several key landmarks like the Winter White House of Harry S. Truman, the Southernmost Point Marker, the Ernest Hemingway House, and the Tenessee Williams House, Key West is a lot of fun for people of all ages to explore.

One of the best ways to explore Key West is via trolley, and one of America’s favorite trolley companies, Old Town Trolley Tours, operates in the area. In fact, Old Town Trolley Tours actually got started in Key West way back in the 1970s. The company knows Key West better than anyone else and features high quality trolleys, lots of stops, discounted entry into various attractions, and more to make your Key West trolley tours as memorable and enjoyable as possible.

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2.Trolley Tours

Trolley Tours
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Old Town Trolley Tours of Key West

Old Town Trolley Tours runs several different trolley tour services in the beautiful city of Key West. Read on to learn all about each one of these options and choose the right tour for you. All tickets can be purchased either on-site in Key West or online for discounted prices, and these trolley tours are open to people of all ages.

Hop On Hop Off Old Town Trolley Tours

The Hop On Hop Off Old Town Trolley Tours are the classic option for taking a trolley tour of Key West. As the name indicates, these tours feature a hop on and hop off system in which riders can choose to get off at any of the stops and hop back on board later on without needing to buy an extra ticket or pay any additional fees. These tours therefore give you total freedom to explore the city and enjoy the magic and history of Key West like never before.

These Key West trolley tours run on a daily basis and begin at 9 am each day, with the final tour leaving at 4.30 pm. Tours run every thirty minutes on average and are fully narrated by expert, friendly guides who can teach you so much about the city in a fun, entertaining way. Old Town Trolley Tours hop on and hop off tours of Key West are one of the best ways to see the city, with a 100% satisfaction guarantee. If you're not happy with the service, you can get your money back, and the cost of a ticket also comes with a special offer to get a second day of trolley tour fun for a discounted price of just $15.

The Hop On Hop Off Old Town Trolley Tours feature 13 unique stops and also come with free admission to Papa's Hemingway Pilar Rum Distillery, as well as passing by more than 100 individual points of interest. All ticket purchases also come with a full color map of the city and a coupon book to help you cut down the costs of your stay in the local area.

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3.More Trolley Tours

More Trolley Tours
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Ghosts and Gravestones Night Tour

The Ghosts and Gravestones Night Tour only operates in the evening and shows off the spooky side of Key West. These tours leave at 7 pm, 8 pm, 9 pm, and 10 pm on a daily basis, but the schedule can vary depending on the time of year, with limited service during certain months, so be sure to check in advance and be sure of your dates before planning your ride on the Ghosts and Gravestones Night Tour of Key West.

As you might imagine, these tours are all about the scarier side of Key West, visiting various allegedly haunted locations around the Old Town area and learning more about why Key West has consistently been classed in lists of the top ten most haunted American cities. Your tour will come with free entry into the East Martello Fort, which is said to be haunted by silhouettes and ghostly orbs. You'll also be able to listen to all kinds of spooky stories from your ghost host guides.

Holiday Trolley Tours of Key West

The Holiday Trolley Tours of Key West only run in December and are all about celebrating the festive season. These tours typically run in the evenings after the sun has set, so everyone can really appreciate the sights of the many lights and decorations that have been put up all around Key West to honor the festive season. For a fun Christmas experience in America’s southernmost town, don’t miss out on these holiday trolley tours.

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3 Best Key West Trolley Tours