Historic Trolley/Train
The Conch Train
Since 1958, the Conch Tour Train has treated guests to a close-up view of the Southernmost City’s most popular places including Mallory Square, The Harry S. Truman Little White House, Overseas Railroad Museum, the Key West Aquarium and more. While on the tour, your engineer offers an interesting and amusing narrative filled with historical facts, trivia and humor, and recounts fascinating stories of the colorful people that make Key West so unique. The Conch Train is not only an informative tour through our island, it is a great mode of transportation around downtown as your ticket allows you on and off privileges all day long!
501 Front Street
(305)294-5161
Key West Trolley
For over 30 years, Old Town Trolley Tours has provided sightseeing tours highlighting the best Key West attractions. Hop aboard one of our trolleys and you’ll experience a delightful combination of transportation and entertainment. This is a great way to get around the island for the day as well as your ticket affords you on and off privileges all day long. Private Trolleys can be rented as well for weddings and other groups.
201 Front Street
(305)296-6688
Guided Walking Tours
Florida Keys Ventures
I have had the pleasure of connecting with a whole lot of great people down here, and one of them is an incredibly gifted entrepreneur by the name of AJ. He not only bustles folks around in his pedicab daily, but he is also the host of a wonderfully fun and informative walking` tour around town. If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the touristic façade that most people never penetrate. That’s why the Southernmost Walking Tour is the best way to immerse you into the history and culture of Key West! When you’re on foot, the world can’t slide past you faster than you can absorb it. You’ll have time – and proximity – to get up close to the region’s culture and natural history. Below are several different tours that his company operate daily.
Tiki Pedicab Experience
TIKI Pedicab Tour (up to 3 people)
Sit and relax on their spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience it's amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West.
First-row, historic, cultural and fun, the only VIP experience tour in Key West.
Key West Historic District Walking Tour
2 Hour Historic Seaport Tour
Ever wondered how the island of Key West was discovered and became so rich? Explore Key West’s history, lore, and legends from the ground up with an intimate walking tour. Whether you want to learn more about the island’s first industries such as shipwrecking and cigarmaking, are curious about local history, or are looking for a fun-filled walk, Key West’s Historic Districts are waiting for you!
History and culture southernmost walking tour
1.5 Hour Downtown Walking Tour
Start your tour at the famous Cuban sandal factory - Kino Sandals before heading off toward the Southernmost Point of the continental United States. Along the way, our incredibly knowledgeable and well-connected local guides will show you the most popular landmarks and introduce you to local culture. By the time you’re finished, you’ll have a uniquely fun perspective of our tiny island!
SPOOKY TIKI PEDICAb Tour
1.5 Hour Tiki Pedicab Tour
Embark on an eerie adventure through Key West's Old Town in a cozy pedicab. Explore ghostly legends, delve into Santeria and Voodoo mysteries, and hear tales of infamous pirates—all while enjoying complimentary drinks. Brace yourself for a thrilling ride into the supernatural heart of Key West!