KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular food & walking tours in Key West. What each trip costs, how long it runs, and who takes you out.
Southernmost Key West Food & Cultural Walking Tour packs 5 tastings, Cuban stops, and Old Town stories into a small-group 3-hour walk.
Most Popular“This was a great food tour. We enjoyed the variety of food dishes and the portion sizes. The tour had a good pace and the history pieces were informative. I highly recommend the tour.”
Taste Key West’s Historic Seaport on a 3-hour small-group walk with 5 tastings, white wine, and end-of-tour key lime pie.
“This was an excellent food tour! Guide, Mike, was awesome! Would recommend this tour to anyone wanting to get a good idea of Key West and taste some of the flavors it is known for.”
A small-group Key West Historic Old Town food walk with 5 tastings, classic conch and Cuban flavors, and a smart route ending at Mallory Square.
“Come hungry. Food was fantastic, Kennarose was a real treat and made the Tour so enjoyable. Walking was easy due to the numerous stops.”
Small-group Key West walk through Bahama Village and historic spots, with Conch Republic lore and Hemingway-era context for $46.99.
“AJ was knowledgeable about the early Cuban and Bahaman cultures that contributed to the historic neighborhoods. He provided historic photos on a laptop computer as we walked. His knowledge of architecture helped understand the community growth. We do recommend this as a cultural experience.”
Ghosts of Key West walking tour: a 90-minute night stroll from Duval Street. Dark island history, eerie stops, and local guides.
“Our guide, Lathan was great.”
Southernmost Key West small-group walk covers shipwreck wealth, Mel Fisher, Audubon House stories, the moved lighthouse, and a Southernmost photo.
“Our tour guide was friendly, knowledgeable and had some interesting historical pictures on his iPad. I would surely recommend him and this tour. It also gave us a sense for the lay of the land on Key West which means we now know where else to go. We passed many of the special spots on…”
A 2-hour Hemingway walk in Key West with lunch, key lime pie, and rum punch, plus on-foot stops tied to Papa’s real life.
“It was great! Learned a lot from our guide! Loved seeing and experiencing details about Ernest Hemingway.”
Old Town Key West literary walking tour with author homes, quote excerpts, and guide commentary. Small group, 90 minutes, $30, English.
“Lovely slow paced walk through charming Old Town Key West! Lots of interesting anecdotes about the many creative individuals who have lived here. The Guide was fun and full facts!”
2-hour Key West haunted pub crawl with a live guide, mobile ticket, and stops like Robert the Doll and Captain Tony’s.
“Kris was amazing. Very engaging. Spoke loud enough to overcome the Key West noise. Knew her stuff. If you like to know the history of Key West, this will give you a great start.”
Key West Cuban-Caribbean food walking tour with 5 tastings, small-group Old Town route, local stories, and recipe takeaways for $90.
“Great tour! Food was delicious! Make sure to bring a hat and sunscreen!”
Taste Key West’s seafood at 5 seaport spots on a small-group walk with 6 tastings, history, photo stops, and recipes to take home.
“Guide was informative and pleasant. She provided a lot of history of key west.”
Adults-only Key West haunted walking tour for $34. A lively 90-minute route with big stories at St. Paul’s, Robert the Doll, and Captain Tony’s.
A 90-minute Key West Historic Seaport walk with three Key Lime Pie samples, maritime stories, and a Key Lime Cocktail stop.
“One of my and my wife's personal highlights of our trip to Key West. Our guide, Kim, took us along the waterfront for key lime pie samples and lots of great information on local history and culture, especially on the influence of the shipping and sponging industries. Kim was super friendly and could not have…”
A 4-hour Hemingway-themed Key West food and drink crawl with museum time, Cuban lunch, cigars, Key lime pie, and Papa rum cocktails.
“This was a fun fully packed tour. Lots to recommend it besides Hemingway. Hotel and mojitos, cigar factory, Cuban lunch, etc. We enjoyed more than we imagined. Great guide. Good value.”
A 90-minute Key West walk with a local guide, stories behind shipwrecking, sponges, and cigars, ending at the Southernmost Point buoy.
Every way to get out on the water, and every reason to stay for the sunset.
