Key West · HISTORICAL TOURS
15 reviewed
This is the shortlist we’d hand a friend: the 15 historical tours worth booking in Key West, each with its price, its verdict, and the one thing to know before you commit.
Taste Key West’s Historic Seaport on a 3-hour walking tour with 5 tastings, shrimp and lobster, plus wine and key lime pie.
“The guide was wonderful - very knowledeable about key west and also the food places we went - all the food was great except i would substitute something else for the lobster mac & cheese maybe conch fritters?”
Taste your way through Key West Old Town with 5 authentic stops, including conch fritters, Cuban favorites, Key lime pie, and more—small group.
“Our guide Chris was very enthusiastic and well informed. We visited many local restaurants and enjoyed delicious specialties. We certainly didn’t need to eat again that day. Thank you Chris!”
A small-group Key West historic walking tour through Bahama Village and the Conch Republic, with tablet photo storytelling and major landmarks.
“We so enjoyed touring the Bohemian District with AJ. We so loved hearing about the history and current culture today. AJ is very knowledgeable and passionate to share. We are excited to come back to Key West and spend more time there. Thank you, AJ.”
Fly high over Key West’s seaport on a classic parasail with long air time, friendly local crews, and optional pro photos.
“We had the best experience Parasailing in Key West. The Parasailing guides were very kind and helpful and even went back to pick up a hat that fell in the water. The experience itself was amazing, Parasailing over beautiful blue water and enjoying the views. Overall it was a very pleasant experience and would recommend.”
Small-group Key West history walk with shipwreck wealth, Mel Fisher, Audubon House stories, and a Southernmost Point photo finish. 90 minutes.
“Alejandro was a great guide and really showed me alot about the history of Key West. Great tour for a solo traveller.”
Sail Key West at sunset on the historic schooner When and If. Enjoy beer and wine, spot dolphins, and help raise sail.
“So much fun! Great time on a historic ship! Would recommend this to anyone who wants to get out to see the sunset or looking for an enjoyable evening.”
Half-day from Key West: ride the Overseas Highway, stop at Bahia Honda, see endangered Key deer, and scout the Blue Hole for wildlife.
“The guide was super nice. The tour was just a little bit too simple for the price. It felt like we were in the van longer than actually exploring or touring.”
Relax on a Marathon sunset cruise past the Seven Mile Bridge with golden-hour photos, calm water, a wine toast, and cool drinks.
“The crew was great on our trip and took us to a few places and provided local knowledge before watching the beautiful sunset.”
Stroll Key West’s Historic Seaport on a small-group Key Lime Pie tour with three samples, pie history, and a Key Lime Cocktail.
“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 had better visual aids and answered our many questions. This was a great introduction of the varieties of key lime pie that exist in Key West, and we could not have had a better and more friendly guide. Highly recommended.”
Key West Art History private walking tour with museum admission, a one-on-one guide, and local artist stops from the Custom House to The Studios.
“Excellent tour. We visited various art related sites which were very interesting. The tour guides were extremely knowledgeable.”
A 90-minute Key West history walking tour from Kino Sandals Plaza to the Southernmost Point, with maps and local stories for $39.
“Enjoyed guide using surface to share pictures to aid in before and how history”
Key West private food tour with 5 authentic tastings, iced coffee, maritime stops, aquarium and seaport sights, and a sweet Key lime finish.
“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 walk at 7:30 pm with haunted mansions and bars, plus Hard Rock Cafe and Duval Street stops.
“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-guided Black History audio tour in Key West with African graves, Union forts, a WWII battleship, and local food for $8.
“Outstanding tour with excellent historical information. Highly recommended. Easy to use iPad narration.”
A smartphone audio walk through Key West’s landmarks and lesser-known stops, paced your way, for $9.75. Starts at the Custom House.
“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!!”
