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Old Town Trolley Tours of Key West has provided vacation guests and locals with more than 30 years of historic tours, news, and events. Each month the Trolley Team publishes upcoming events in Key West for visitors and residents to enjoy.
Verify info of all events & locations listed. Dates & times may vary due to COVID-19.
“The best way to visit all the Key West attractions in one weekend is to hop aboard Old Town Trolley”
If you’re visiting during the Key West Labor Day Weekend, don’t forget to include the Old Town Trolley Tour in your itinerary. The best way to visit all the Key West attractions and historic sites in one weekend is to hop aboard Old Town Trolley when you arrive and see the best sites first. We operate our normal business hours during the holiday weekend and guarantee you will enjoy the experience. This allows you to plan your vacation around the activities that interest you and your family the most. You can hop on and off at your leisure!
Thursday to Labor Day Monday
Key West Labor Day event featuring more than 200 different beers, including many award-winning microbrews. Benefits Key West Sunrise Rotary Club of the Conch Republic. Beer tastings, food and musical rhythms round out the weekend activities. For more information, please call 305-295-6519.
1 Whitehead Street
If you’re looking for family-friendly things to do for Labor Day, visit the Key West Aquarium. Located in Mallory Square, guests love to view colorful sea creatures, touch conchs and even pet sharks. Peer through the window of wonder, part of a living red mangrove ecosystem, and enjoy the breathtaking beauty found at this innovative attraction. Kids love the Key West Aquarium’s petting and feeding shows as well as its up close and personal touch tank.
1 Whitehead Street
After you’ve explored the Key West Aquarium, step back in time as you discover Key West’s unique maritime heritage and how it became the richest city in the United States. Learn about the early history of the island and all the sunken treasure that was found from the Isaac Allerton Shipwreck at this one-of-a-kind Key West Museum.
When you’re ready to soak up the sun, climb aboard Fury Water Adventures’ Ultimate Adventure trip. It’s an all-day excursion perfect for watersports enthusiasts and thrill seekers. Snorkel, parasail, Jet Ski, kayak and more in the island’s crystal clear water. Guests also enjoy complimentary breakfast and lunch while relaxing on Fury’s state-of-the-art catamaran. For more information, please call 888-976-0899.
Learn more about Key West’s rich history this Labor Day! Take a tour of the Truman Little White House, Florida’s only presidential site. Nestled in Truman Annex, Present Harry S Truman made the Little White House his winter home from 1946 to 1952. The Little White House is the perfect place to find out more about President Truman’s life and American government. For more information, please call 305-294-9911.
If you are a Key West resident, take advantage of the Old Town Trolley Tours Hometown Pass program. After your registration is verified, you will receive free admission to the historic Key West Tour each time you bring a full paying adult guest. Learn more about the Hometown Pass today.
Explore the haunted past of Key West before the Halloween crowds start up. See some of the city’s spookiest sites. Drive past the Artist’s House where Eugene lived and where a servant gave him a one-of-a-kind handmade doll he named Robert. Climb aboard the Trolley of the Doomed for a chilling “frightseeing” tour you’ll never forget.