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“We enjoyed everything about this tour. Marissa our tour guide provided a nice balance of history, food and local lore. The walking was pretty easy and now there are so many new places to try. Well worth it!”
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.
“This was a great tour. Our guide was very knowledgeable and personable and we had a wonderful morning exploring Key West. I highly recommend this tour.”
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.
“This was not scary. Did not receive any free T-shirt as advertised.”
Key West Cuban-Caribbean food walking tour with 5 tastings, small-group Old Town route, local stories, and recipe takeaways for $90.
“It was great. Kyle actually added an extra garden tour for us.”
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.
“It was great loved the history and the food was fabulous”
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.
“This walking tour was the perfect slice of Key West—sweet, relaxed, and full of local flavor. From the very first stop, it was clear this wasn’t just about eating key lime pie (though wow, did we eat some excellent pie), but about understanding the history, rivalries, and passion behind it. Kim was knowledgeable, funny, and…”
A 4-hour Hemingway-themed Key West food and drink crawl with museum time, Cuban lunch, cigars, Key lime pie, and Papa rum cocktails.
“Too big of a group! 16 people!! Kyle was very nice. Very hard to hear most of the time even in indoor places. In addition, we are now (next morning) having serious intestinal issues. This is the first (of many) Viator experience where we were disappointed!!”
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.
