KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 8 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“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.
“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.”
Soar 8–15 minutes above Key West’s Historic Seaport with Sunset Watersports, see the Keys below, and optionally buy onboard photos.
“It’s a lot of fun and anyone can do it! Ian and Joey were great and the photos they took were priceless”
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!!”
Every way to get out on the water, and every reason to stay for the sunset.