See All that Key West Has to Offer

Soar over Key West in a helicopter ride or taste the cuisine. 

Lloyd's Tropical Bike Tour

Hi, my name is Lloyd and I would like to share my unique bicycle tour of Key West with you. What I provide during this leisurely ride along our quiet streets and hidden lanes is a hands on sensory rich field trip.  limes, mangoes and more. Try the fragrance of frangipani (plumeria), jasmine, gardenias and allspice. Roll along quiet streets lined with classic examples of Shotgun, Bahamian, Victorian, Eyebrow and Conch style houses. Visit the location of the homes of famous authors, and hear their untold secrets.  Explore the Key West wildlife Center and visit a lush botanical garden inside a historic fort. This tour is for people of all ages. Take a ride with Lloyd and discover the real Key West.

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Rodriguez Cigar Rolling Tour

In 1971, the Rodriguez family found a new beginning on the beautiful island of Key West and established the Rodriguez Cigar Factory. Founded in 1984, we stand as the oldest operating cigar manufacturer in the Florida Keys. Rodriguez Cigars are exclusively constructed with vintage leaves that have been cured, aged and constructed through the traditional Cuban manufacturing process.  Take a step back in time and experience an old world family tradition that began in Cuba in 1947. Learn the traditional way of rolling a cigar with the Oldest Cigar company in the Florida Keys, on the Rodriguez Cigar Rolling Tour.  Our master cigar rollers will guide and instruct the full process of manufacturing cigars from start to finish.

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Key West Food Tours

Unique guided small group experiences designed to introduce you to authentic Key West flavors.   Step off Duval Street and into local restaurants on this 3 hour culinary adventure through the historic district of Key West.

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Haunted Key West

Our interactive tours are authentic explorations of the other side, featuring unusual and entertaining guides and tours created by renowned ghost hunter, David L. Sloan. Key West is consistently ranked as one of the most haunted cities in the United States. We look forward to helping you experience that first hand.

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Ghosts and Gravestones Tours

Old Town Trolley Tours invites you to explore our premier “frightseeing” tour, Ghosts & Gravestones Night Tour. Prepare yourself for an evening of fun, scares, and ghost stories as you are guided through some of America’s most haunted cities: Boston, Key West, Savannah, San Diego and St. Augustine. Hear local tales of murder and mayhem, mixed with a good dose of humor and history. In Boston, walk amongst the dead in burying grounds nearly 400 years old. See a mischievous doll named Robert with a mysterious curse in Key West. Visit us in Savannah for EXCLUSIVE nighttime entry into River Street’s Perkins and Sons Ship Chandlery for a haunting experience. Hear stories of ghosts that haunt the ships at the San Diego Maritime Museum. And in St. Augustine, you’ll see the town’s most haunted building, The Old Jail, for an up close and personal encounter.

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Island Tours with Air Adventures

As soon as you lift off, you are soaring with the birds over Key West's historical landmarks. This 20-mile tour circles the island of Key West, with views of Smather's Beach, The Southernmost Point, Fort Zachary Taylor, Sunset Key, Wisteria Island, Mallory Square, and world-famous Duval Street! Perfect for families with small children - not too short, not too long! (10 minutes).

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Up the Keys!

Enhance your Key West vacation with an interactive road trip excursion Up The Keys! Visit several of the best islands in the Florida Keys and learn the history, culture, ecology, and legends of these extraordinary islands. We travel along the Overseas Highway and visit the premium attractions in the Keys. Get up close to the wildlife as if you're on a safari. We look for the endangered Key Deer, ALLIGATORS, and more! Of the many things to do in Key West, this is one you shouldn't miss! We'll even pick you up at your Key West hotel or Key West vacation rental.

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Paradise Bike

Paradise Bike Tours provides guests with a fun and adventurous experience in the city of Key West. While doing this, our company seeks to positively contribute to our community, by being strong advocates for bicycle safety.  We want to share the fun, freedom and love of bike riding in Key West with everyone! Our tours are perfect for every type of rider, from the inexperienced to the professional bike rider.

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Historic Key West Walking Tour

Discover the beauty and captivating culture of the Conch Republic during a Historic Key Walking Tour. This leisurely 1.4-mile stroll through a portion of the city's Old Town is highlighted by architectural gems, tropical plants and unique cultural sites and attractions as well as the nautical history that make the United States' southernmost city so unique.

The beauty of Key West can be found walking the streets. During your mile and a quarter stroll through old town, your guide will point out the blend of architecture, plant life and culture that make Key West unique. 

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