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Old Town Trolley Tours of Key West

Old Town Trolley Tours of Key West

Old Town Trolley Tours of Key West

Hop on and Hop off of this fully narrated sightseeing tour of Key  West, featuring over 100 points of interest. The trolley makes 13 stops  so you can disembark along the way for shopping, attractions and dining.  

 Tour All Day! 

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Ghosts & Gravestones Tour

Old Town Trolley Tours of Key West

Old Town Trolley Tours of Key West

 Join your gravedigger guide aboard the "Trolley of the Doomed" for an  evening through Key West's darker side. Ghosts & Gravestones of Key  West offers guests an adventure into the strange and macabre past of  this Southernmost City. 

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Key West Cooking Show

Old Town Trolley Tours of Key West

Key West Cooking Show

Step into the Key West Cooking Show, where history, culture, and cuisine come together in a lively and immersive culinary experience. Our expert chefs will guide you through the preparation of authentic Conch Cuisine, inspired by generations of Key West traditions.

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Southernmost Food Tasting & Cultural Walking Tour

Southernmost Food Tasting & Cultural Walking Tour

Southernmost Food Tasting & Cultural Walking Tour

 Savor the real Key West on this flavorful food and cultural walking  tour. First-time visitors and food lovers will enjoy local must-try  dishes like authentic Cuban food, conch, and Key Lime pie. 

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Key Lime Bike Tours

Southernmost Food Tasting & Cultural Walking Tour

Southernmost Food Tasting & Cultural Walking Tour

Key Lime  is perfect for first time visitors, as well as visitors that are limited on  time and still want to see everything Old Town has to offer! 

A truly unique and unforgettable tour.

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Historic Seaport Food & Cultural Walking Tour

 Dive into a handpicked lineup of iconic seafood dishes, from lobster mac  & cheese to freshly caught fish tacos. As you stroll along the  waterfront, keep an eye out for manatees and sharks. 

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Insider's Hemingway Experience

  Step into Hemingway’s world with skip-the-line access to his iconic  home. You’ll also visit a historic cigar factory, sip craft spirits at a  Hemingway’s family distillery, and dine on Papa’s favorite dishes. 

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Key West Bar Crawl – Cocktails

Key West Bar Crawl – Cocktails

 Explore hidden watering holes with a fun local guide leading the way.  You’ll sip craft cocktails, swap stories,  share laughs, and leave with new friends, a buzz, or both. 

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Drag Shows at Aqua

Key West Bar Crawl – Cocktails

 The Aqua Drag Show offers the best nighttime entertainment in Key West. Dive into a world of fun and entertainment at Aqua Nightclub Key West! Enjoy live shows, drag performances, fresh cocktails, and more. 

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Whiskey Rick's Key West Tours

Whiskey Rick's Key West Tours

 A history  nerd who enjoys sharing stories, Whiskey Rick has been giving tours in Key West for  years.  Reviews of his tours frequently comment on how he blends comedy with an engaging style. 

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Mallory Square Sunset Celebration

Mallory Square Sunset Celebration

Mallory Square Sunset Celebration

The Key West Sunset Celebration invites everyone to partake in watching the glowing pink and red sun sink into the horizon. The nightly festival hosts visitors from all over the world who come to take part in the magicians, jugglers, clowns, psychics, local musicians, artists, and food vendors that combine for an incredible cultural experience. 

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Red Barn Theater

Mallory Square Sunset Celebration

Mallory Square Sunset Celebration

 The Red Barn Theatre has become a cultural cornerstone for the Key West  community while building a national reputation. Many well-known and very  talented people are a part of the Red Barn Theatre’s story.  Jimmy Buffett, Philip Burton, Terrence McNally,  Jerry Herman, and Tennessee Williams have all made the Red Barn a part  of their cultural experiences in Key West. 

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Waterfront Playhouse

Mallory Square Sunset Celebration

Waterfront Playhouse

 The Waterfront Playhouse has been entertaining Key West audiences for  over 80 years. Located in the heart of Key West’s historic Mallory  Square, this not-for-profit, professional theater attracts locals and  tourists with a wide range of theatrical fare. The Playhouse is an  intimate 150-seat theater located steps from Key West’s nightly sunset  celebration. 

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What To Do In Key West

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