KEY WEST
Ranked by traveller popularity
The 10 most popular historical tours in Key West. Here's what they actually deliver, who runs them, and what they cost.
Walk Key West’s Historic Seaport with a local guide, tasting at 5 stops from pink shrimp to lobster mac and finishing with 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.”
Key West Historic Old Town food tour with 5 authentic tastings, iced coffee, conch fritters, Cuban flavors, and key lime pie. 2.5 hours.
“Come hungry. Food was fantastic, Kennarose was a real treat and made the Tour so enjoyable. Walking was easy due to the numerous stops.”
A small-group 1.5-hour walking tour of Key West’s Historic District, with local stories on the Conch Republic, Bahama Village, and Hemingway-era ties.
“Alejandro was awesome! Key West is great. The tour was great. What made it extra special is that our guide, Alejandro, was amazing. He was fun, he was interesting, and he was very knowledgeable. Highly recommend.”
Parasail above Key West’s historic seaport with Sunset Watersports, fly up to 15 minutes, and enjoy Marine Sanctuary views from the dock.
“It’s a lot of fun and anyone can do it! Ian and Joey were great and the photos they took were priceless”
Walk Key West’s southern edge with a small group: shipwreck stories, Mel Fisher, Audubon House, a moved lighthouse, Hemingway tales, and a buoy 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.”
Two-hour Key West sunset sail on a historic schooner. Spot dolphins and turtles, sip beer and wine, help raise sail, small group.
“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...”
Florida Keys Nature & History tour from Key West with 20+ bridges, Bahia Honda, 7-Mile Bridge, Key Deer, and Blue Hole wildlife.
“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.”
Marathon sunset cruise with Seven Mile Bridge views, calm Keys waters, cool drinks, and occasional live acoustic music. 1.5 hours.
“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!!”
Walk Key West Historic Seaport, taste 3 key lime pies, and finish with a key lime cocktail on a small-group tour.
“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 90-minute private walking tour through Key West’s art stops, starting at the Custom House museum, with museum admission included.
“Excellent tour. We visited various art related sites which were very interesting. The tour guides were extremely knowledgeable.”
