SAFETY IS OUR #1 PRIORITY: In order to assure you, our valued guests, have the safest and most comfortable sightseeing experience, Old Town Trolley Tours has implemented a number of new disinfecting and safety measures including: Daily deep disinfecting procedures for our vehicles and facilities; Additional throughout the day disinfecting on high volume touch points and sanitizing solution dispensers on every vehicle and at our sales locations.

Learn about Key West's lucrative (ship) wrecking industry. Hear the stories of success and disaster of Henry Flagler's railroad... the railroad that went to sea. Listen to the legends of the fierce Calusa Indians that were said to leave the remains of their enemies on the beaches of Key West, thus creating Key West's first name, Cayo Hueso... Island of Bones.

Tour at your own pace!
Old Town Trolley Tours allows you to get off at any of its convenient stops. When you're ready, just re-board and it's on with the tour.

On your tour you'll also find out where to dine, shop, and just relax and have good time. The Old Town Trolley Tours are Key West's most comprehensive tours, covering over 100 points of interest. The guides have been extensively trained and are proud to share the history, lore and legends of Key West.

Included Free with your Trolley Ticket is admission to the Sails to Rails Museum. Guests to Sails to Rails will journey through the Age of Sail, a time when tail ships plied the treacherous waters of the Caribbean, Gulf of Mexico and Florida Keys from the 1500 to early 1900’s. These waters were once filled with treasure-laden Spanish Galleons, dreaded Pirates, merchant ships and more as the New World made its riches known to all who sailed her waters. A visit to Sails to Rails is one of the most comprehensive overviews of Florida Keys and Key West history a visitor can obtain.

Note: Your eTicket is good for all day use from 10:00am, with the last re-boarding at 4:00pm. If you chose to stay on the trolley, the tour is approximately 90 minutes. You may "hop on" and "hop off" as many times as you like during the hours of operation.

TIP: Spend more time sightseeing! You can purchase admission to popular attractions along this hop-on/hop-off tour route directly from this Trusted Tours and Attractions website. Get your tickets in advance and experience one of the best vacations you can have!

Old Town Trolley Tours and Transportainment are registered trademarks of Historic Tours of America.

Don't just visit Key West... RELIVE IT!

Are you ready for some "spirited" fun? Join us on a spine-tingling adventure through Bone Island.

After receiving your souvenir T-Shirt you will embark on a 2-hour haunted walking tour of Old Town Key West. Along the way we will explore a former morgue and a mansion with a tragic past.

At all three pubs, guests can enjoy "spirits" of their choice. As you sip your drink our Ghost Host will recount the haunted tales of each pub. Liquid "spirits" are not included in the price of the tour and must be paid for separately.

Bring your camera and an open mind for a night you won't forget!

Discover the perils of the shipwrecking industry as you journey back in time to 1851. See how the rewards of this dangerous profession made Key West one of the richest cities in America. Artifacts and video presentations, as well as a 65-foot observation tower, make the museum a unique experience. See and hear film clips, interviews and actual underwater footage in the re-created salvage warehouse. Experience the mesmerizing tale of the Isaac Allerton, one of the richest shipwrecks in the history of Key West. Many of the artifacts on display come from her watery grave. Learn about Asa Tift and other individuals who made their fortunes in the exciting and perilous world of wreck salvage.

Then climb to the top of the lookout and imagine yourself spotting the wrecks of Spanish galleons and turn-of-the-century cargo ships like the wrecking captain's of old. A top attraction in Key West for kids of all ages.

The Ultimate Water Adventure is truly a water sports lover's dream. Sail seven miles out from Key West to the only live coral reef in the continental United States onboard a modern 65-foot catamaran while enjoying a complimentary breakfast. When you arrive at the reef, the adventure truly gets started. You can snorkel to the colorful reef and view marine animals, including barracudas, sea cucumbers and urchins as you explore this diverse undersea ecosystem. The friendly crew provides all the instructions that you need.

After an hour of discovery on this amazing Atlantic Ocean barrier reef, enjoy a picnic lunch as you sail 45 minutes west into the Gulf of Mexico to link up with the floating platform that will serve as the venue for hours of exciting water activities, such as jet skiing, parasailing and enjoy the Banana Boat. You can also swim in the warm water or just relax on the roomy open-air sundeck. In addition to an afternoon snack and unlimited complimentary water and soft drinks throughout the day, enjoy free wine and beer as you sail back to Key West exhausted from a day of fun in the sun.

For more than three decade, Fury Watersports has been providing locals and out-of-town water enthusiasts the adventures of a lifetime in this tropical paradise. Make your reservation and get an eTicket today so you can join Fury on the next Ultimate Water Adventure Tour.

Are you looking for the ultimate Key West tradition? Come along and do the "Duval Crawl".

Key West is famous for its bars. Day or night the pubs are always rocking on this small island. On the Key West Pub Crawl Tour you will experience some of the most famous and entertaining drinking establishments in the Florida Keys.

This 2.5 hour event begins downtown, moves through the historic seaport and then returns to Duval Street. Everyone will have a choice of a domestic beer or mixed drink at each bar. You will also receive a free souvenir T-shirt to commemorate the event. Enjoy the sites and bars of Key West with our "masters of mixology" as you embark on your party in paradise.

Whether it's the casual Keys atmosphere, live music, or Caribbean drinks you are after, your Key West Pub Crawl will be an adventure to remember. Try the Caribbean Breeze at Rick's if you dare!