Nothing is more thrilling than the prospect of a long weekend around the corner. Since the two most prominent holidays that feature that most welcome Monday off, Labor Day and Memorial Day, occur in the warmer months, visions of outdoor grills, swimming pools, and chilling hard on the old Barcalounger are among the most desirable. However, if you decide you want to level up from the common ‘staycation’, there’s an island situated in the southernmost reaches of the Sunshine State that has been delighting visitors for decades. With its pioneer spirit, off-the-grid appeal and beach town charm, Key West is your ticket to adventure!More Info
In the land of key limes, errant roosters, partying and sunsets, every day is never the same as the one before. With its turquoise waters and hang-loose state of mind, time moves differently here in paradise and that is a very good thing. It’s an easy place to visit but is it ever tough to leave. You forget about the rest of the world here, but you are reminded of it just enough. If you plan on visiting the Conch Republic and want to drop some coin on a bit of a shopping spree, this tiny island is big on options.More Info
Spectacular sunsets, warm ocean breezes and a laid-back island atmosphere create the perfect setting for a budding romance or rekindling a long-term relationship. These are some of the enduring images and themes featured in many of Hollywood’s most romantic movies. Key West offers this and more. A favorite destination for royalty, political leaders and literary legends, this tropical oasis is an idyllic backdrop for a first date or special getaway celebrating a long-term relationship. Take that special someone on a romantic, unforgettable trip to experience attractions that allow couples to enjoy the sights while spending quality time together.More Info
Planning a girls weekend in Key West? We’ve got you covered with everything from where to stay, what to eat, the hottest bars and the best activities on the island.More Info
The Yankee Freedom III is the official ferry of the Dry Tortugas National Park. 70 miles from Key West at the Dry Tortugas National Park lies Fort Jefferson, the largest masonry structure in the western hemisphere. Aboard the Yankee Freedom guests will travel in air conditioned comfort, enjoy delicious breakfast and lunch, snorkel gear, showers and guided tours of this Civil War fort that has been called the eighth wonder of the world.
If you are planning a Key West vacation, spending some quality time at the beach is a top priority on your travel itinerary. Boasting temperate waters and more than 3,400 hours of annual sunshine, the beaches of Key West are some of the most popular destinations on this tropical island paradise. You can enjoy the sun, sand and warm water as well as a variety of activities like swimming, snorkeling and fishing.More Info
Key West is famous for being the southernmost city in the continental United States. When you visit, it’s essential that you make it to the southernmost point on the island, found at the intersection of Whitehead Street and South Street. Here, you’ll see the landmark Southernmost Buoy (a required photo opp) and a whole host of other “southernmost” attractions that make for a fun Key West afternoon.More Info
An island of only five square miles, Key West is a pretty easy place to navigate. It’s also filled with hidden gems ripe for discovery.
To paraphrase former Key West resident and famed poet Robert Frost, the road less traveled in Key West can make all the difference. And that’s exactly what you get when you hop aboard Old Town Trolley – the road less traveled far beyond Duval Street.More Info
The Casa Marina was built by Henry Flagler for his passengers on the overseas rail road in 1920 and exudes splendid Mediterranean charm. Sophistication and luxury mesh beautifully with this ideal Key West locale offering visitors a heavenly retreat in the midst of historic sites, natural beauty and enticing attractions. Ocean view rooms, an expansive private beach and a gorgeous swimming pool make it easy for guests to relax and appreciate every moment of their stay. The Casa Marina recently emerged anew, even grander, after a magnificent renovation of the guest rooms, pool and other areas and is now part of the Waldorf Astoria collection of hotels.More Info
Perhaps one of the most popular destinations on the island of Key West, Duval Street is the main drag of downtown, running north and south from the Gulf of Mexico to the Atlantic Ocean. Although it is not much more than a mile in length – this is where the heartbeat of the city comes to life with a diverse array of restaurants, shops, world famous pubs and attractions.More Info
Located at the center of the historic Key West waterfront, Mallory Square Things to do is filled with attractions, unparalleled shopping, fabulous restaurants and the world famous sunset celebration. You haven’t visited Key West until you’ve experienced Mallory Square.More Info
Introducing the Old Town Trolley Hometown Pass Program. Residents of Key West and Monroe county can take advantage of our tour for FREE when accompanied by an adult paid guest.* It’s free to join and easy to use.More Info
Old Town Trolley Tours offers discounted rates for charters, group ticket sales and special events. All of our Key West trolley rentals can be custom designed to meet your group’s specific transportation needs.More Info
A visit to Key West is always an adventure and if you’re heading that way, you’re in for great time. The Southernmost City offers a host of interesting things to see and do, fascinating history and gorgeous natural scenery. When you begin your planning, make sure to plan how you’re going to get from one place to another. Here are some of the best ways to get around Key West.More Info
To most, Key West is thought of as a beach town with great parties, endless sandy coastline and year-round sunshine. But did you know its history stretches much farther than its shoreline? Read on for some of the best fun facts about this island oasis.More Info
The Southernmost City in the USA, Key West is an oasis surrounded by gorgeous crystal waters. It’s here that you’re invited to come as you are, kick back and let go of all the stresses of hectic day-to-day life. Learn some of the top reasons to visit Key West.More Info
Welcome to Key West
Key West is a beautifully historic town filled with impressive attractions and sites. Maximize your time for sightseeing by taking Key West shore excursions from Old Town Trolley. Whether you take the tour purchased from your cruise excursions desk, or take the tour with on-and-off privileges purchased from Old Town Trolley directly, you will have time to shop, visit attractions, and find your way to some of our most famous landmarks.More Info
Old Town Trolley Tours of Key West has provided vacation guests and locals with more than 30 years of historic tours, news, and events. Each month the Trolley Team publishes upcoming events in Key West for visitors and residents to enjoy.More Info
Planning a two-day trip to Key West?
Follow this guide to get the most out of your time on the island.Buy Tickets More Info
So, you’re heading to the southernmost city in the USA? Lucky you! There is so much to do and see in this island paradise, from intriguing attractions and historical sights to water sports, entertainment and world-famous points of interest. If you want to see the best of Key West in one day, hop aboard Old Town Trolley.Buy Tickets More Info
Get MORE out of your summer in Key West aboard the iconic Old Town Trolley and see the best first!
Get a taste for the Caribbean heritage that is so much a part of Key West. In Bahama Village, which is a 12-block area between Whitehead and Fort and Angela and Catherine Streets, you’ll be able to see the original area in which the first black Bahamian settlers arrived in the 19th century. Sample true Bahamian culinary recipes in a variety of restaurants, stop in for a refreshment in one of the bars and shop in the Bahama Market. All the flavors, culture and traditions that this historic neighborhood represents come alive through the many streets.More Info