We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. Key West, FL/
    3. Land Activities/
    4. Bike Tours/
    5. Key West Bike Tour: Historic Old Town Landmarks
    Why travelers choose Greetwell
    Curated by our team

    Every experience is selected and approved for quality and safety

    Personal concierge

    Real humans available to help before, during, and after your booking

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else

    Easy booking

    Reserve in minutes with flexible cancellation on most experiences

    Greetwell

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners

    Concierge Support

    • Help Center
    • (650) 414-7338
    • Contact our team

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Key West Bike Tour: Historic Old Town Landmarks

    Explore Key West's iconic landmarks with a local guide on two wheels

    From$45/ person

    Duration

    Approximately 2 Hours

    Ideal For

    15 people

    Includes

    Bike, water, key lime pie

    Highlights

    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.


    1. Ride a comfortable bike along a relaxed 4-mile route
    2. Visit the Southernmost Point and other iconic landmarks
    3. Hear engaging tales of famous residents and local history
    4. Stay hydrated with complimentary bottled water
    5. Enjoy a slice of authentic Key lime pie after the tour

    What's Included

    1. Bike and helmet
    2. Bottled water
    3. Ponchos if needed
    4. Sunscreen
    5. 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.

    FAQs

    Q: What time does the tour start and how long is it?

    A: The tour departs at 10 AM and 2 PM daily and lasts about 2 hours.

    Q: What landmarks will we see on the tour?

    A: 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.


    Q: What if I’m a cruise-ship visitor with limited time?

    A: The tour is quite suitable for visitors with a shorter visit, since it covers the main sites in about two hours.

    Q: Where do we park?

    A: Please allow yourself plenty of time to find parking. There are spaces behind the building for $5 per hour (pay meter), or you can park at Two Friends Patio for $20 all day (pay the attendant or pay the bartender if the attendant is unavailable).


    Q: Is the tour suitable for children or beginners?

    A: Yes, the ride is on beach-cruiser bikes and described as accessible for most fitness levels. The minimum age is around 10 in some bookings.

    Experience provided by Key Lime Bike Tours
    Experience provided by Key Lime Bike Tours

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #WJRMWX

    Person

    $45

    Ages 8+

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

    Search all experiences

    Discover what we've curated for you

    Cancellation policy

    Free cancellation or reschedule up to 24 hours before tour time.

    Meeting location

    122 Ann St Key West, FL 33040

    4.9 stars• 422 reviews

    Review summary

    4.9
    Excellent
    422 reviews•Google Maps

    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.

    What people are saying

    Review 1 of 5
    5/5

    Based on a recommendation from a friend, my girlfriend, and I decided to take a chance and go on the key line bike tour. We met up with James our tour guide. He was a character to say the least. His knowledge of Key West and surrounding area was outstanding. He explained to us in detail all about Key West and its history.. He kept us entertained with Personal stories as well. James also made sure that we had plenty of water to drink and made frequent stops to make sure we will safe. In addition, he offered to take pictures so that we would have memorabilia from this entertaining trip.

    Photo of William Smith

    William Smith

    October 11, 2025

    Review 1 of 1
    5/5

    Based on a recommendation from a friend, my girlfriend, and I decided to take a chance and go on the key line bike tour. We met up with James our tour guide. He was a character to say the least. His knowledge of Key West and surrounding area was outstanding. He explained to us in detail all about Key West and its history.. He kept us entertained with Personal stories as well. James also made sure that we had plenty of water to drink and made frequent stops to make sure we will safe. In addition, he offered to take pictures so that we would have memorabilia from this entertaining trip.

    Photo of William Smith

    William Smith

    October 11, 2025

    Nearby activities

    Thumbnail

    Key West Beach Cruiser Bike Rental

    From$20
    Thumbnail

    Key West Ghost Hunt with Real Investigation Gear

    $32.50/ person
    Thumbnail

    Key West Day Sail with Snorkel & Kayak Lunch

    From$134/ person
    Thumbnail

    Key West Sunset Sail with Wine & Craft Beer

    $109/ person
    Thumbnail

    Key West Private Boat Charter with Snorkeling

    $652
    Thumbnail

    Key West Day Sail on 105ft Schooner America 2.0

    $56/ person