Hemingway's Key West: A Literary Journey

Immerse yourself in the world of Ernest Hemingway on this authentic walking tour of Key West. Visit the places where he lived, worked, and played, and indulge in food and drink samplings along the way.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • The Ernest Hemingway Home and Museum - You will meet your tour guide outside the front gate of the Hemingway House. Then a guided tour will take you to the real places that Hemingway lived, worked, and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, his…
What's Included
  • Lunch
What's Not Included
  • Gratuities
Additional Information

This guided walking tour will lead participants to the actual locations where Hemingway lived, worked, and enjoyed his leisure time. The tour includes stops at places where he watched and refereed boxing matches, the location where he docked his boat, the Pilar, the bookstore that sold his works, and his first apartment in Key West where he completed “A…

Location
The Hemingway Home and Museum
Whitehead Street
Please meet your tour guide OUTSIDE the front gate. Please arrive 15 minutes early.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(105 Ratings)
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Trail636378
Feb 2, 2026
Fantastic and fun - Caleb did a great job giving our group information on Hemingway and stopped for delicious food along the way too. Highly recommend!
Review provided by Tripadvisor
Junebugfareast
Feb 1, 2026
Great time. We enjoyed the tour - Learned a lot and had a good time on this tour. Caleb was a knowledgeable and entertaining guide into the life of Hemingway.
Review provided by Tripadvisor
Callie_g
Jan 31, 2026
Caleb was very... - Caleb was very knowledgeable about Hemingway and Old Town. He also shared a lot of information about Jimmy Buffet as an added bonus! For future tours, it would be great to know an ending point, as we had left our bikes all the way back at the Hemingway House.
Review provided by Viator
Jimln8039lh
Jan 3, 2026
Hemingway and the wild days of Key West - Our guide really enhanced our knowledge of Hemingway and his life on Key West. O had no idea how crazy the island was even back then and how Hemingway fit right in. Would definitely recommend to others.
Review provided by Tripadvisor
Ladonna_p
Nov 30, 2025
Great! - It was great! Learned a lot from our guide! Loved seeing and experiencing details about Ernest Hemingway.
Review provided by Viator
George_d
Aug 9, 2025
Fun, interesting Caleb is... - Fun, interesting Caleb is a good tour guide. Very knowledgeable. The food was good key lime pie was great.
Review provided by Viator
611kristif
Jul 20, 2025
Perfect for Hemingway fans (or anyone!) - This tour was amazing! Our tour guide Caleb was very knowledgeable and great fun! The food was excellent as well. We loved it!
Review provided by Tripadvisor
Richard_b
Jun 23, 2025
Excellent tour - Great tour! Caleb was very engaging, funny and knowledgeable. Answered all our questions. Very good lunch. If you’re here in the summer months I suggest the early time. Also suggest going to the Hemingway Social Club after the tour for a drink and a picture with Ernest
Review provided by Viator
Debmink
Jun 14, 2025
One Amazing Tour - If you are a Hemingway buff- or not, this is the tour for you. Caleb is a superb tour guide. My husband knows a lot about Hemingway, but Caleb is the “cream of the Hemingway crop”. We walked a ways, but it didn’t seem like it because we were totally engaged throughout. The lunch was incredible- homemade and fresh from a local deli and then there was Kermit’s famous key lime pie for dessert. Caleb makes this tour one of the best in Key West. (We’ve been on many food tours in Key West and this is our favorite)
Review provided by Tripadvisor
Jill_p
Jun 5, 2025
Caleb was awesome. One of... - Caleb was awesome. One of the best tour guides we have had in our numerous travels. Would highly recommend this tour for even more info on Hemingway. The key lime pie and wrap was very good.
Review provided by Viator
From $99
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).