KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 14 most popular food & drink 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.
“Do not snack ahead! The food choices represented the history of the city and were delicious. Mike, our tour guide drew upon his culinary background to share behind the scene insight on local fishing and the vast number of restaurants in the trade. Time and money well spent!”
Key West Bight boat day with jet ski, snorkeling, kayaking, inflatables, parasailing, and lunch plus beer included for 21+.
“The excursion was fun, plenty of time to do everything, and the food was plentiful. Highly recommended for anyone with teenagers.”
Sail Key West at sunset on the America 2.0 schooner. Drinks and hors d'oeuvres included, wildlife sightings, and a shot at the green flash.
Sail Key West at sunset on a modern 3-deck catamaran with live music, unlimited open bar, and light appetizers for about 2 hours.
“It was exactly as expected....drinks and sunset on a big catamaran. Fortunately, it was not super crowded. The staff was great and the boat was clean.”
A 2-hour Key West sunset sail on the Sandie Cat with an open bar, finger foods, and live music on the upper deck.
“Beautiful cruise and an amazing sunset. We enjoyed the food, drinks and music”
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.”
Snorkel two Key West reef spots on The Miss Valyn, then sail into sunset with beer, wine, and champagne on a 3-hour catamaran.
“Great crew, bottomless drinks (after you finish snorkeling), helpful, attentive, and just a fun experience..”
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.
“Caleb was very knowledgeable about Hemingway and Old Town. He also shared a lot of information about Jimmy Buffet as an added bonus! For future tours, it would be great to know an ending point, as we had left our bikes all the way back at the Hemingway House.”
Key West Cuban-Caribbean food walking tour with 5 tastings, small-group Old Town route, local stories, and recipe takeaways for $90.
“Must do while in Miami! Go be a Papi for a day enjoying some Cuban coffee, with a fedora and a cigar.”
Key West secret walking food tour through Old Town. Cuban bites, conch fritters, rum tasting, and chocolate-dipped key lime pie.
“Easy going tour that was a perfect amount of food, sites and sounds and context of where we were and what we were looking at. Right amount of walking. Kitty was great as a tour guide. Didn’t get in the way of Key West - right amount of questions and allowing us to take in…”
Spot dolphins near Key West, snorkel reef waters with included gear, and cruise back with unlimited beer and soda on a comfy 55-foot yacht.
“It was perfect experience! Very knowledgeable and friendly stuff, clean boat, good equipment for snorkeling.”
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!”
A 2-hour Key West walk tracing Hemingway’s life with three local tastings, plus stops tied to his writing, fishing, and boxing days.
Every way to get out on the water, and every reason to stay for the sunset.
