KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular 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“What a great way to experience the local flavors! All the restaurant choices were phenomenal and Kieran was very knowledgeable as he is a conch!”
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.
“You shouldn’t miss the opportunity to take part in this experience! My bride and I had an amazing ball!!”
Ghosts of Key West walking tour: a 90-minute night stroll from Duval Street. Dark island history, eerie stops, and local guides.
“That was the best ghost tour I've been on. Ki was so enthusiastic and entertaining! And very knowledgeable too. It was very interactive and fun.”
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.
“Fun, interesting Caleb is a good tour guide. Very knowledgeable. The food was good key lime pie was great.”
Old Town Key West literary walking tour with author homes, quote excerpts, and guide commentary. Small group, 90 minutes, $30, English.
“Guide was very informative! He said he would send us some info, I'll enjoy revisiting the memory from that. Lots of Key West history that I wouldn't have known otherwise.”
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.
“Overall was very enjoyable.. Our tour guide Corlie was great and made the trip very interesting.”
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 90-minute Key West walk with a local guide, stories behind shipwrecking, sponges, and cigars, ending at the Southernmost Point buoy.
A 90-minute Old Key West walk tied to Jimmy Buffett’s stories, ending at Capt Tony’s, with key lime pie and an adult drink included.
Key West secret walking food tour through Old Town. Cuban bites, conch fritters, rum tasting, and chocolate-dipped key lime pie.
“Very nice tour that highlighted by several local food places.”
Private Key West walking tour with flexible stops, great photo help, and local stories from Old Town to Mallory Square and beyond.
“We had a fantastic tour today with “Whiskey Rick”, our tour guide. Private tours are the way to go. We asked a ton of questions, and he definitely tailored the tour to what we were looking for (history and current happenings). We did not walk one block on Duval, but covered a large portion town…”
Every way to get out on the water, and every reason to stay for the sunset.
