Explore Key West's iconic landmarks with a local guide on two wheels
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Approximately 2 Hours
15 people
Bike, water, key lime pie
Pedal through Old Town Key West with a local guide and uncover the island's history, landmarks and colorful stories. Cover four easy miles, pause for photos, and finish with a refreshing slice of Key lime pie.
Riders must be at least 8 years old. Please arrive 10–15 minutes early to find parking and prepare for departure.
Free cancellation or reschedule up to 24 hours before tour time.
The tour departs at 10 AM and 2 PM daily and lasts about 2 hours.
The guided ride covers key sites in Old Town Key West including Mallory Square, Hemingway House, Truman’s Little White House, the Southernmost Point Buoy and others.
The tour is quite suitable for visitors with a shorter visit, since it covers the main sites in about two hours.
122 Ann St Key West, FL 33040
Key West bike tours don't get much better than this, according to travelers who consistently rave about the experience. The guides here, particularly James and Lenny (who, along with Maria, appear to be the owners), come up as genuine local experts who know how to balance entertainment with education. James gets called "quite the character" and "hilarious" by multiple reviewers, while Lenny earns praise for being personable and welcoming to even the "stupid questions." What stands out is how these guides tailor the experience to individual groups, checking what guests have already seen and adjusting accordingly. The 2.5-hour tours cover a large swath of the island, giving first-time visitors an excellent orientation to Key West's layout, history, and vibe. Beyond the guided tours, the rental side of the business gets equally strong marks for being easy to work with. Several reviewers mention the owners' flexibility when plans change, and one regular customer highlights how the team goes above and beyond by calling to confirm details like bike sizes for taller riders and offering delivery and pickup service. Thoughtful touches pop up throughout the reviews: cold water provided generously in the heat, stops at air-conditioned spots like the Eco-Discovery Center, help with crossing busy streets, and complimentary key lime pie at tour's end. The bikes themselves are easy to ride (one person joked they managed even while hungover), and the flat terrain makes for a comfortable ride despite the humidity. Local restaurants apparently recognize these folks by name, with one bartender noting they're "true ambassadors" to community causes, which speaks to their genuine investment in Key West beyond just running tours.
Wow, what a great tour and a fun way to see Key West! Our guide Lenny was super informative and told us about history, architecture, plants and tidbits about the island. They even gave us ice cold water! The bikes are in excellent shape and there are many stops and bathroom breaks along the way. Make this a MUST when you visit.
Samantha Kern
April 2, 2026
Wow, what a great tour and a fun way to see Key West! Our guide Lenny was super informative and told us about history, architecture, plants and tidbits about the island. They even gave us ice cold water! The bikes are in excellent shape and there are many stops and bathroom breaks along the way. Make this a MUST when you visit.
Samantha Kern
April 2, 2026