Top Key West Cultural Tours

Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide.
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Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era, each of it’s 5 stops revealing a new secret.
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If you’re looking for the ultimate Key West experience, join the 'Duval Crawl' pub crawl!
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Discover why Key West is one of the most haunted locations in the country on this 90 minute walking tour that starts at the corner of Duval and Caroline Streets, and led by your experienced guide and storyteller.
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Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West.
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Experience the best of Key West on the famous Conch Tour Train!
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You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District.
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You will enjoy a delicious and spirited change in attitude while we serve up a bucket list walk through time as we eat, drink and discover the local fuels and hear about the historical and hysterical tales of legends and lore told through the eyes of your swashbuckling local guide.
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Join us every weekend for the Old Town Literary Walking Tour, a stroll through downtown Key West, illuminating stories of writers that have called our island home.
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Join us for a 1.5-hour adventure!
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Travel The Keys is a guided tour and concierge company based in Key West, Florida.
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Join us for the best walking tour in Key West!
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Key West Highlights- “The best walking tour in Key West!” Join Key West's unofficial "mayor" and his sidekick "Oliver" (Key West's most famous mascot) as they take you on a pleasant 2 hour stroll through the historic Old Town streets.
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Historic Homes & Designs of Key West- "The best historic home walking tour in Key West!" Join Key West's unofficial "mayor" and his sidekick "Oliver" (Key West's most famous mascot) as they take you on a wonderful and informative 90 minute stroll through the celebrated Old Town neighborhoods where you'll discover many of the beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community.
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You will be amazed by how much history and culture our small island has!
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There’s so much to see and do in just 1 1/2 hours of driving from Key West to Marathon.
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In just 1 hour of walking, learn the history, culture, and cuisine of Key West.
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Stroll along the Gulf of Mexico, enjoying the island’s best happy hours, then watch the famous Key West sunset.
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Walk through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation.
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Discover the cuisine and culture of historic old Key West.
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Key West Highlights Private Tour- “The best walking tour in Key West!” Join Key West's unofficial "mayor" and his sidekick "Oliver" (Key West's most famous mascot) on a pleasant 2 hour private stroll through the historic Old Town streets.
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