KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular historical tours in Key West. What each trip costs, how long it runs, and who takes you out.
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.
Most Popular“You shouldn’t miss the opportunity to take part in this experience! My bride and I had an amazing ball!!”
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.
“Great host - AJ took us all over the old town sharing lots of info on the area and the people that created Key West. Really enjoyed our time!”
Soar 8–15 minutes above Key West’s Historic Seaport with Sunset Watersports, see the Keys below, and optionally buy onboard photos.
“Take the trip even if you are afraid of heights! Everything about the trip was FUN!! The boat ride was fun! The guys were fun! The parasailing was fun! And the music was fun!! You won’t regret it!!”
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.”
Sail Key West at sunset on the historic schooner When and If. Help raise sails, spot dolphins and sea turtles, and enjoy beer/wine.
“Historic wooden schooner built by Alden yachts for Gen Patton in 1932. Captain and 2 woman crew were awesome and the sunset was beautiful! 2 hour adventure was perfect with a chance for everyone to participate in the tasks at hand...”
A half-day nature and history trip from Key West: Overseas Highway bridges, Bahia Honda, Key Deer Refuge, and a Blue Hole wildlife stop.
“First off I wanna say we had Carol as a tour guide and she was terrific. She is very knowledgeable about the history of the keys.”
A relaxed 7-Mile Bridge sunset cruise from Marathon with calm water, golden-hour photo light, a toast, and live music at times.
“We surprised my parents with a sunset tour. With the sunset setting on the Atlantic side of Marathon, the views were spectacular, waters super calm and the staff beyond amazing! Mike, Jason and Tyler were beyond accommodating and knowledgeable answering our questions. We will definitely be using this company again!!”
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…”
Private Key West art history walk with museum entry included, a local guide, and stops at local galleries and shops over 90 minutes.
“My husband and I wanted to get an insider’s perspective on the beautiful community that is Key West, and Lindsey totally delivered! We saw some beautiful art, both from past and present artists living on the island, we chatted with an artist at Read more”
A 90-minute Key West walk with a local guide, stories behind shipwrecking, sponges, and cigars, ending at the Southernmost Point buoy.
A 2.5-hour Key West private food tour with 5 tastings, iced coffee, museum and aquarium admissions, and an end at Mallory Square.
“Sharry was wonderful!!!! Highly recommend!!!!!! Her food choices were excellent, her tour knowledgeable yet comfortable and laid back, and it was so nice to stray from the beaten path a bit!”
Private Key West haunted history walking tour with a local guide, haunted mansions and bars, and optional drink stops starting at 7:30 pm.
“Our guide was very knowledgeable and ensured our tour was fun and enjoyable. We enjoyed the stories. Good mix of history and ghost stories. Definitely recommend!”
Self-paced Black history audio tour in Key West: Higgs Beach graves, a Union fort, churches, conch salad, and key lime pie for $8.
“Outstanding tour with excellent historical information. Highly recommended. Easy to use iPad narration.”
Self-guided Key West audio walk from the Custom House. Hear Hemingway, Sloppy Joe’s, Jimmy Buffett spots, and key lime pie lore.
“You can go at your own pace. If you want to stop and explore a certain spot, you can pause the tour. It's very easy to follow and give lots of good info!!”
Every way to get out on the water, and every reason to stay for the sunset.
