Old Town Trolley
Old Town Trolley
Old Town Trolley
Old Town Trolley
Limited Spaces Available! For reservations call (866) 945-7917. Spaces are extremely limited this time of year so book early to ensure the date you want.
Old Town Trolley


Stops at all of Key West's best attaction such as:

  • Mallory Square
  • Historic Waterfront
  • Simonton Row
  • Bahama Village
  • Garrison Bight Marina
  • Smathers Beach
  • White Street Pier/Higgs Beach
  • Southernmost Point

Tour Summary

Relax and enjoy the coastal breezes in the open-air car of our old-fashioned trolley as you enjoy a relaxing and informative tour of historic Old Town on Key West, Florida. Enjoy the entertaining description and narration of our knowledgeable and gregarious tour guide. You will learn all about this isles legendary past that includes indigenous culture, swashbuckling buccaneers, opportunistic wreckers, the United States Navy, a legendary writer, and even a president. Some of the islands earliest known inhabitants, the Calusa, were known to leave the bodies of slain adversaries along the coast of Key West, so that their bones would bleach in the tropical sun. When the Spanish arrived on Key West, they called it Cayo Hueso or the Island of Bones. Pirates, who hijacked merchant vessels, would sometimes dock in Key West. Wreckers once turned sailors misfortunes into a highly profitable industry by collecting the salvageable cargo of ships after they broke up on the reef. Key West entered the Twentieth Century after Henry Flagler finally, after much difficulty, built a railroad line through the Keys.

If you are interested in history, then this is the perfect tour for you. Our charming and knowledgeable tour guides will tell you all of the most interesting aspects of Key Wests history.

While riding the trolley, you can step off the trolley at one of the many convenient stops along the way to take a closer look at one of the many attractions or landmarks on the route. You can take your time and rejoin the tour at your own

It is your responsibility to make sure you are aware of and understand all restrictions pertaining to this tour before booking online or over the phone. It is your responsibility to ensure that you are medically qualified and within any limits listed below in order to participate in this activity. No refunds will be given to those who reserve a spot and can not participate due to the restrictions listed below. For more information please read our cancellation policy and terms and conditions page or call our staff with any questions regarding your ability to participate.

Key West Vacation is always interested in your tour experience with us. We hope you enjoyed your tour and love to hear comments.

Bob Smith

I have been to the Bahamas many times, but Old Town Trolley is one of my favorite trips! It includes everything that everyone should do here. As a Bahamas veteran, I can say only the best about this experience!

Jim Peters

Thanks to the professional guides! I was a bit worried about kayaking because I had never done it before, but the instructions were great and I had such a good time!

Richard Dixon

The best way to discover nature! ( ͡° ͜ʖ ͡°)