Explore at your pace
Free cancellation
Book now, pay later
Guided tour
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Board the trolley and discover Key West's sun-soaked streets over 1 or 2 days, from the famous Southernmost Point to quaint Old Town lanes.
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Travel through 13 stops with trolleys arriving every 30 minutes, giving you the freedom to explore at your own pace and revisit favorite sights.
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Enhance your adventure with 2 free walking tours, complimentary Sails to Rails Museum entry, and discounts worth $50 at Key West's best attractions.
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Ride in open-air comfort as live narration unfolds tales of shipwreck salvagers, Hemingway's six-toed cats, and the island's colorful pirate past.
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Hop off at beloved landmarks like the Key West Aquarium, the Ernest Hemingway Home, vibrant Mallory Square, and the iconic Southernmost Point buoy.
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1 or 2-day unlimited hop-on hop-off trolley tour
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Live narration in English
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2 free guided walking tours
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Free admission to the Sails to Rails Museum
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Discount coupons worth up to $50
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You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
- 12 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
102000What our guests say
Tara
Dec 2025Verified booking
Keron
Jun 2025Verified bookingTammy
Mar 2025Verified bookingBonnie
May 2025Verified booking
Larry
Mar 2025Verified booking
What's not allowed
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Pets are not permitted on the trolley.
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Smoking, vaping, and the consumption of alcohol are not allowed aboard the trolley.
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Large luggage or oversized items that may obstruct aisles or seating areas are prohibited.
Accessibility
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The trolley tour is wheelchair accessible at designated stops (Stops #1, 2, 3, 6, 7, 8, 9, and 10) with motorized lifts available.
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Advance notice is required to ensure proper accommodations for individuals with mobility impairments and those using wheelchair devices.
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Guests with limited mobility can remain on the trolley for the full 90-minute narrated loop without needing to hop off.
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Your guide dogs and service animals are welcome on board the trolley.
Additional information
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Seating is available on a first-come, first-served basis.
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Your ticket grants re-boarding privileges throughout the day, allowing you to explore Key West at your own pace.
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Specific details related to the add-ons in your ticket, like the free walking tours, museum entry, and discounts, will be provided in the ticket after booking.
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No printout required! Just show your mobile voucher to the driver and collect your bus ticket.
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You can join the tour from any one of the stops in Key West.
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