Discover Key West - Guided Tours
Insider's Hemingway Experience
2 exclusive tours - 3 food & 3 drink tastings - 4 hours
Retrace Ernest Hemingway’s footsteps through Old Town on this immersive Insider’s Hemingway Experience, which includes entrance into his Key West home and estate, an exclusive look inside a family-run cigar-rolling factory, a visit to the Pilar Distillery Social Club, and tastings of iconic Key West flavors. Along the way, enjoy must-eat classics like Cuban roast pork, Key Lime Pie, and—of course—rum, just the way “Papa” liked it, while learning about the life, legends, and lasting influence of Hemingway and the island he loved.
Hemingway Food & Walking Tour
2 Hour guided walking history and food tour
Meet your guide at the Hemingway Home and explore the real places where Ernest Hemingway lived, worked, and spent his time in Key West. This engaging walking tour visits historic bars, harbors, and literary landmarks closely tied to his life on the island. Along the way, enjoy several local food tastings that highlight classic island flavors. Led by knowledgeable guides, this two-hour tour is moderately paced and suitable for most fitness levels.
Jimmy Buffet Food & Walking Tour
90 minute guided walking history and refreshments tour
Meet your guide at Margaritaville on Duval Street and step into the Key West that helped turn Jimmy Buffett into a legend. This fun, easygoing walking tour hits the bars, stages, and island hangouts that inspired his songs, stories, and laid-back lifestyle, finishing at the iconic Capt. Tony’s Saloon. Expect great music lore, classic Key West history, and plenty of “you-had-to-be-there” stories from entertaining local guides. The tour is moderately paced, suitable for most fitness levels, and includes light island refreshments.
Tiki Pedicab Experience
2 Hour TIKI Pedicab Tour (2 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!
Key Lime Bike Tour
2 Hour guided bicycle tour with a slice of key lime pie at the end!
An easy, relaxed ride through Old Town that’s perfect for getting your bearings. You’ll cruise past historic homes, waterfront spots, and key landmarks while hearing real stories about the island’s history and culture. Informative, fun, and unhurried — a great first-day way to see Key West and decide what you want to explore next.
Key West UFO Tour
An after-dark, oceanfront experience exploring Key West’s lesser-known UFO history. Guided by locals, small groups use military-grade night-vision scopes to scan the sky while hearing eyewitness accounts, coastal lore, and stories tied to the Keys, the Bermuda Triangle, and beyond. A curious, immersive night under the stars that blends history, mystery, and hands-on exploration.
Typically meeting at the White Street Pier (after dark)
The Conch Train
1 Hour circuit detailing the history of Key West and touring the Old Town or downtown area.
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
Old Town Trolley
90 minute Hop on and off narrated trolley tour with highlights across the entire island.
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