Key West History Tours: Our 4 Picks

1.Key West Historic Seaport Food & Walking Tour

★★★★★★★★★★5.0 · 642 reviews · 3 hours (approx.) · from $93Our pick

Spend about three hours walking from Eaton Street Seafood Market to Mallory Square, stopping for five food and drink tastings. Guides such as Mike, Larry, Corley and Sharon share Key West stories, local food tips and restaurant advice. Expect seafood, Cuban flavors, white wine and key lime pie, with limited allergy and diet options.

“Do not snack ahead! The food choices represented the history of the city and were delicious. Mike, our tour guide drew upon his culinary background to share behind the scene insight on local fishing and the vast number of restaurants in the trade. Time and money well spent!”

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2.Key West Historic Bahama Village & Hemingway Heritage

★★★★★★★★★★5.0 · 252 reviews · 1 hour 30 minutes (approx.) · from $46

Walk 1.4 to 1.8 miles through Old Town, Bahama Village, and quieter side streets with guides AJ, Alejandro, or Leo. Hear about Conchs, Cuban and Bahamian influences, Hemingway’s famous pool, historic architecture, the Green Parrot, and Key West’s unusual past. Expect a warm-weather walk for up to 12 people.

“AJ was an excellent guide, he told the history of the island clearly, and was very engaging. Would highly recommend this walking tour.”

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3.Parasailing over the Historic Key West Seaport

★★★★★★★★★★4.5 · 210 reviews · 1 hour (approx.) · from $49

Meet Sunset Watersports at 201 William Street for a one-hour parasailing trip above Key West Seaport and the Florida Keys National Marine Sanctuary. You can fly alone or with two others, and crews such as Ian, Joey, Wyatt, Tyler, or Logan may handle your boat. Expect clear instructions, music, optional toe dips, and photos for purchase.

“Listen to the instructions and you will be fine. Very cool experience! The crew was great, very experienced. Photo package definitely worth it!”

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4.Southernmost Key West History and Culture Small-Group Walking Tour

★★★★★★★★★★5.0 · 124 reviews · 1 hour 45 minutes (approx.) · from $39Best value

Walk 1.4 to 1.8 miles through Key West with a local English-speaking guide, often AJ or Alejandro. Learn how shipwrecks shaped the town, hear stories about Mel Fisher, Audubon House, the lighthouse, and Hemingway, then finish at the Southernmost Point buoy. The 10-person maximum keeps the walk personal.

“AJ was a great tour guide. He shared interesting information about the sites along the way and had recommendations for things to do in the area. He was also patient when I accidentally went to the wrong starting spot. I recommend this tour if you want to get your bearings on Key West and see a lot of main sites in a short amount of time.”

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