Want to explore the cultural, architectural, haunted, and historical side of Key West? There’s a walking tour for that. The island is only four miles long and two miles wide (at its widest), so exploring Key West on foot is the way to go. Whether you’re in town for a week or a weekend, this selection of the best Key West tours will help you make the most of your visit.

1. Intro to Key West’s Top Sites

Play tourist for a day with A Happy Passport’s free, self-guided walking tour of Key West’s top sites. The tour takes you to all the best places in Old Town, including Mile Marker ‘0’, the Southernmost Point Buoy, Ernest Hemingway Home and Museum, Duval Street, and Mallory Square.

2. Key West Architecture Tour

Leave the smartphone in your room and hoof it through town with the Old Island Restoration Foundation’s printable self-guided architecture tour of Key West. The tour takes just over an hour, and includes stops at over 50 historic structures, like the Truman Little White House, Oldest House in South Florida, and Audubon House. You’ll also stop at the “eyebrow” house at 512 William St., aptly named for its upper windows shaded by a roof overhang - a style completely unique to Key West!

3. Key West Cemetery Tour

The historic 19-acre cemetery on Pauline Street in Old Town is known for its many eccentricities - pet burials, resident iguanas, the “I Told You I Was Sick” headstone, and grand, New Orleans-esque family plots with open roof structures and masonry buildings - all of which make for an unforgettable walking tour. The Historic Florida Keys Foundation offers a tour of the cemetery twice a week.

4. Key West Ghost Tour

The Key West Ghost & Mysteries Tour ventures into the world of spirits with stops at some of the spookiest and most haunted locations in the neighborhood. Explore the hidden side of the island and its colorful characters with this guided 90-minute Key West walking ghost tour. Stops include the graveyard, Hemingway’s Casa Antigua, and Artist’s House, the original home of the haunted Robert the Doll.

5. Duval Crawl / Key West Bar Crawl

Stretching from the Gulf of Mexico to the Atlantic Ocean, the world famous Duval Street is known for its hedonistic nightlife, eclectic galleries and boutiques, and one of the densest concentrations of bars in the world - 43 to be exact. Grab a drink from each to complete the infamous Duval Crawl and gain lifelong bragging rights.

Consider joining a tour of Key West’s best watering holes led by someone in-the-know. Key West Food Tours hosts a guided bar crawl that takes you to the craftiest bars and hidden gems in town. Sip on five signature cocktails while enjoying fun food tastings along the way. If you’re craving some sustenance, the tour company also hosts a Historic Seaport Food walking tour for you to get to know the island’s Cuban and Caribbean culinary influences.

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Give your feet a rest from the best walks in Key West with a sail into the sunset. Now for a limited time, book The Gates Hotel’s Key West Sunset Cruise special offer and hop aboard the state-of-the-art Fury Catamaran. Choose from our best rates and special offers when you book direct with The Gates Hotel, a Conde Nast award-winning Key West destination.

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