Key West Trolley Tour: Explore Historic Island

Experience the rich history of Key West on a hop-on hop-off trolley tour. Discover the island’s fascinating past, from Indians and pirates to the Civil War. Don’t miss the free admission to the Sails to Rails Museum!

Duration: 1 hour, 30 minutes
Cancellation: 24 hours
Highlights

Old Town Trolley Tour of Key West (Route)

Operating Schedule: Tours depart from boarding locations approximately every 30 minutes. Guests with vouchers can board at any Old Town Trolley boarding location. Wheelchair accessible stops include Stops #1, 2, 3, 6, 7, 8, 9, and 10. Open daily from 10am to 4:30pm. The last full tour leaves from Mallory…

What's Included
  • Free admission to the Sails to Rails Museum
  • Two free walking tours included
  • Narrated tour
  • Ages 0-3 free
  • Local taxes included
What's Not Included
  • Gratuities
  • Food and drinks
  • Tour closed October 23-24
Additional Information

The hop-on hop-off tram journey around Key West provides an outstanding opportunity to discover this ancient island. Seat yourself comfortably as your knowledgeable tour leader delves into the past, recounting the era of Native Americans, buccaneers, salvage teams, and the Civil War. You’ll experience a comprehensive view of Key West through this Old…

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.4
(1522 Ratings)
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Donald_m
Jan 28, 2026
This was great ! Each... - This was great ! Each driver was different and all so knowledgeable about Key West history. The hop on and hop off was so easy.
Review provided by Viator
Roberta798
Jan 26, 2026
Great tour - Our guide, Patrick, was excellent. Shared lots of information and history about Key West. Highly recommend this tour!
Review provided by Viator
Stark2071
Jan 26, 2026
Will go back again. - Drivers were knowledgeable and personable. Stops were conveniently located. SO convenient to get on and off anywhere all day long. Saved our legs. Definitely worth the cost. Even if you did it every trip here, you’ll learn different things from different drivers.
Review provided by Tripadvisor
Anonymous
Jan 25, 2026
Highly recommend! - The trolley and the train are different tours. The trolley goes all around the island. The train stays in Old Town. Our guide was terrific and gave us a lot of history. We thoroughly enjoyed it!
Review provided by Viator
Shahid_r
Jan 22, 2026
Comfortable Key West tour - Comfortable tour with good live commentary by the driver. The weather was cold snd windy. So the bus ride was quite appropriate for us.
Review provided by Viator
Jodi_b
Jan 21, 2026
A great way to explore Key West - Fun and informative! Our two drivers were great and the trolleys were clean and comfy. This was a good way to get the lay of the land and hear some basic history about the island.
Review provided by Viator
Susangt8109fr
Jan 21, 2026
Sing, sing sing went the trollley! - Tom, our driver and guide was so knowledgeable and an excellent entertainer, too! We laughed while learning the history of the Keys and various buildings. We sang show toons. Very enjoyable!
Review provided by Tripadvisor
Annmariestone
Jan 18, 2026
Winter get away! - Drivers were experienced, fun and informative! They all made it a unique experience. Buses ran often so we weren’t waiting too long! We had a 2 day pass which was very helpful!
Review provided by Tripadvisor
Georgeo579
Jan 18, 2026
Hop-On Hop-Off Trolley, Key West, FL - Of course cruise ship docked and the lines to get on the trolleys were long, but they did a good job of bringing empty trolleys around. Driver was very friendly, courteous and full of interesting facts and figures. He did very well negotiating heavy vehicle and pedestrian traffic. Unfortunately, we did not get off at any of the stops because we were afraid we would have trouble getting back on and returning to the ship before sailing, since we passed many stops where we had a full trolley and there was a large group waiting for a trolley, so driver called in each time and we continued.
Review provided by Tripadvisor
Mdnl88
Jan 18, 2026
Driver spent his time soliciting tips - We got on and off different trolleys, all were fine until the last trolley driver who spent his time soliciting tips! He was on a microphone so you couldn’t miss it when he called out each person who tipped him as they stepped off. Then one guy got off and dropped a tip in his bucket and the driver said “on a budget are we?” I hope the owner sees this as it was embarrassing for the man he did this to. What does this clown say to Europeans who don’t participate in tipping? He even has a sign taped to his chair with a bar code to his Cash App! Everyone is expected to tip each time they get on and off this trolley after paying $55 per person? I totally understand tipping but this guy was so wrapped up in it that he made you tipping him all he talked about! He spoke of other things that had no business being talked about on a trolley and had zero to do with Key West! Couldn’t wait to get back on the cruise ship after seeing how he treated tourists.
Review provided by Tripadvisor
From $56
up to 9 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).