Key West · HEMINGWAY & OLD TOWN HISTORY WALKS
14 reviewed
Key West wears a century of wreckers, cigar makers and literary bad behaviour on its shady lanes. Here are the best Old Town history walks — Hemingway’s house and cats, the conch mansions, the Southernmost Point — with durations, group sizes, and which guides really know the salvage-era gossip.
Small-group Key West Old Town food walk with 5 tastings, Cuban coffee and key lime pie, plus rum cocktails. 3 hours.
“This experience is a must do in Key West! The food, drink, and cultural history made for a 3 hour tour was fun, delicious, and entertaining! Totally amazing!”
Taste Key West’s Historic Seaport on a 3-hour walking tour with 5 tastings, shrimp and lobster, plus wine and key lime pie.
“The guide was wonderful - very knowledeable about key west and also the food places we went - all the food was great except i would substitute something else for the lobster mac & cheese maybe conch fritters?”
Step into Harry Truman’s Key West winter White House. Guided tours, period rooms, and standout stories for a laid-back historical stop.
“Greg was a great guide - informative and entertaining. The grounds are beautiful, and the period pieces in the house make you feel a part of history.”
A small-group Old Key West walking tour built around Jimmy Buffett, with key lime pie and a final stop at Capt. Tony’s.
“Huge Jimmy Buffett fans so this peek into his Key West life was fun! Caleb was wonderful - funny and entertaining!”
A small-group Key West historic walking tour through Bahama Village and the Conch Republic, with tablet photo storytelling and major landmarks.
“We so enjoyed touring the Bohemian District with AJ. We so loved hearing about the history and current culture today. AJ is very knowledgeable and passionate to share. We are excited to come back to Key West and spend more time there. Thank you, AJ.”
Ghost tour of Key West at 8pm with a local guide. Walk Duval Street’s dark sites, hear island legends, and cover major stops in 90 minutes.
“Great tour and awesome level of enthusiasm, will have to go again soon! I wish there was an even longer tour!”
3-hour Key West small-group tour with 5 Cuban and Caribbean tastings, Old Town history, and e-recipes for $90.
“We had Max as our guide and thoroughly enjoyed the whole experience! The tour is paced perfectly never felt rushed and portions were great. The mix in the experience was fantastic. We had our first stop at a restaurant that is on everyone's must list! We went to places my sisters and I probably wouldn't have gone otherwise! Max gave us a great recommendations not just for the places we experienced but also places close by those. We took enough of those recommendations that I was worried he would think we were stalking him we so him so often over the next few days!!!”
Small-group Key West history walk with shipwreck wealth, Mel Fisher, Audubon House stories, and a Southernmost Point photo finish. 90 minutes.
“Alejandro was a great guide and really showed me alot about the history of Key West. Great tour for a solo traveller.”
Taste Key West and follow Ernest Hemingway on a small-group walking tour with lunch, key lime pie, and local rum punch.
“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.”
Key West’s Old Town literary walking tour with book excerpts, writer haunts, and a library kickoff. Small group, 90 minutes, $30.
“Scott was a great guide! I really appreciate the emailed links for more information on the authors we discussed.”
Key West Haunted Pub Crawl: a guided 2-hour nighttime walk through historic bars and eerie landmarks, with ghost stories.
“Very nice time good stories and good bars We enjoyed learning a lot of the scary stories and history of the area”
A 1-hour guided visit to the Truman Little White House in Key West. See Eisenhower and Edison connections for $25.
“I knew nothing of Truman little white house before our Key West vacation. Definitely a must see! A trolley tour stop does not do justice to this important piece of Americana history. Vice President Truman was left totally in the dark concerning the atom bomb before FDR’s death. I left this tour with a much broader knowledge of not only learning about this great man but a better understanding of the ending of WW2.”
Key West seafood and seaport walking tour with 5 tastings, local history, conch pronunciation, and a small-group lunch in 3 hours.
“Guide was informative and pleasant. She provided a lot of history of key west.”
Adults-only Key West ghost walk with a live guide, haunted landmarks, and grisly true-story vibes in 90 minutes for $34.
“We had an amazing tour! Our guide was knowledgeable and fun to listen to!! We enjoyed hearing the spooky history of the island!”
