The 4 Best Key West History Tours

1.Key West Historic Seaport Food & Walking Tour

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

Explore Key West’s Historic Seaport with a small group and local guides such as Mike, Larry, Coraly, and Sharon. You’ll stop at five food venues for pink shrimp, lobster mac and cheese, a Cuban mix sandwich, wine, and key lime pie, with local stories along the way. Plan for heat, moderate walking, and a seafood-heavy menu.

“The guide was fantastic and knowledgeable. Gave a great view and taste of the keys. Provided local knowledge and stories. Very enjoyable and tasty tour. Thanks.”

Check availability →Read our full review

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 Key West with local guides such as AJ, Alejandro, or Leo. Expect Bahama Village, historic homes, architecture, Cuban and Bahamian connections, the Conch Republic, a famous pool, the 1825 landmark, and the Green Parrot Bar. The 12-person limit keeps the tour personal.

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

Check availability →Read our full review

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 boat outing above Key West Seaport. Fly solo, as a pair, or three together, with 8 to 15 minutes in the air and a possible toe dip on request. Crews including Ian, Joey, Logan, Wyatt, and Tyler handle safety and photos.

“Joey and Marty were the best. We felt safe and had an awesome time. Definitely but the pictures! Worth the money! Dolphins swimming underneath us was a bonus!”

Check availability →Read our full review

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 historic Key West with a local English-speaking guide, often AJ or Alejandro. Hear how shipwrecks built the town, learn about Mel Fisher and Hemingway, see Audubon House and the lighthouse, then finish at the Southernmost Point buoy. Expect sun, steady walking, and a group of no more than 10.

“Great tour and tour guide (AJ). Hit the highlights of the history of Key West. Plus some current happenings. With dinner recommendations.”

Check availability →Read our full review