15 Best Historical Tours In Key West

Food, Food & Drink, Food & Walking Tours, Historical Tours, Key West, Tour Reviews, Tours, Walking Tours

Key West Historic Seaport Food & Walking Tour

/ June 4, 2026

1.Key West Historic Seaport Food & Walking Tour

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.

Key West Historic Old Town Food Tour with 5 Authentic Tastings

/ June 4, 2026

2.Key West Historic Old Town Food Tour with 5 Authentic Tastings

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.

★ 5.0

“Come hungry. Food was fantastic, Kennarose was a real treat and made the Tour so enjoyable. Walking was easy due to the numerous stops.”

289 reviews2 hours 30 minutes (approx.)From $108.00by Secret Food Tours

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Food & Walking Tours, Historical Tours, Key West, Tour Reviews

Key West Historic Bahama Village & Hemingway Heritage

/ June 4, 2026

3.Key West Historic Bahama Village & Hemingway Heritage

Small-group Key West walk through Bahama Village and historic spots, with Conch Republic lore and Hemingway-era context for $46.99.

★ 5.0

“AJ was knowledgeable about the early Cuban and Bahaman cultures that contributed to the historic neighborhoods. He provided historic photos on a laptop computer as we walked. His knowledge of architecture helped understand the community growth. We do recommend this as a cultural experience.”

252 reviews1 hour 30 minutes (approx.)From $46.99by Florida Keys Ventures

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Historical Tours, Key West, Parasailing, Tour Reviews

Parasailing over the Historic Key West Seaport

/ June 4, 2026

4.Parasailing over the Historic Key West Seaport

Soar 8–15 minutes above Key West’s Historic Seaport with Sunset Watersports, see the Keys below, and optionally buy onboard photos.

★ 4.5

“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!!”

210 reviews1 hour (approx.)From $49.95by Sunset Watersports

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Food & Walking Tours, Historical Tours, Key West, Tour Reviews, Tours, Walking Tours

Southernmost Key West History and Culture Small-Group Walking Tour

/ June 4, 2026

5.Southernmost Key West History and Culture Small-Group Walking Tour

Southernmost Key West small-group walk covers shipwreck wealth, Mel Fisher, Audubon House stories, the moved lighthouse, and a Southernmost photo.

★ 5.0

“Great historical summary and tour of Key West! Our tour guide AJ was fun and had a great sense of humor and lots of knowledge about Key West!”

124 reviews1 hour 45 minutes (approx.)From $39.99by Florida Keys Ventures

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Cruises & Boat Tours, Evening Experiences, Historical Tours, Key West, Schooner Sailing, Sunset Sails & Cruises, Tour Reviews

Key West Historic Schooner When And If Sunset Cruise

/ June 4, 2026

6.Key West Historic Schooner When And If Sunset Cruise

Sail Key West at sunset on the historic schooner When and If. Help raise sails, spot dolphins and sea turtles, and enjoy beer/wine.

★ 5.0

“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...”

114 reviews2 hours (approx.)by Sunset Sail Key West

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Florida Keys Tours, Historical Tours, Key West, Shark & Wildlife Tours, Tour Reviews, Tours

Florida Keys Nature & History Tour from Key West

/ June 4, 2026

7.Florida Keys Nature & History Tour from Key West

A half-day nature and history trip from Key West: Overseas Highway bridges, Bahia Honda, Key Deer Refuge, and a Blue Hole wildlife stop.

★ 5.0

“We wanted the half day tour. Unfortunately, they did not have a driver and canceled the event on me that morning. We did not receive any notice about the the early arrival of 9 am and could not adjust our schedule.”

110 reviews4 hours (approx.)From $109.00by Up The Keys Tours

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Cruises & Boat Tours, Evening Experiences, Florida Keys Tours, Historical Tours, Key West, Sunset Sails & Cruises, Tour Reviews

Marathon: Historic 7-Mile Bridge Sunset Cruise

/ June 4, 2026

8.Marathon: Historic 7-Mile Bridge Sunset Cruise

A relaxed 7-Mile Bridge sunset cruise from Marathon with calm water, golden-hour photo light, a toast, and live music at times.

★ 5.0

“The crew was great on our trip and took us to a few places and provided local knowledge before watching the beautiful sunset.”

55 reviews1 hour 30 minutes (approx.)From $124.99by Solé Watersports

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Food & Walking Tours, Historical Tours, Key West, Tour Reviews, Tours, Walking Tours

Key Lime Pie Walking Tour of Key West Historic Seaport

/ June 5, 2026

9.Key Lime Pie Walking Tour of Key West Historic Seaport

A 90-minute Key West Historic Seaport walk with three Key Lime Pie samples, maritime stories, and a Key Lime Cocktail stop.

★ 5.0

“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…”

38 reviews1 hour 30 minutes (approx.)From $69.88by Tart Tales

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Historical Tours, Key West, Private, Tour Reviews, Tours

Key West Art History Private Tour

/ June 5, 2026

10.Key West Art History Private Tour

Private Key West art history walk with museum entry included, a local guide, and stops at local galleries and shops over 90 minutes.

★ 5.0

“Excellent tour. We visited various art related sites which were very interesting. The tour guides were extremely knowledgeable.”

35 reviewsFrom $59.99by Key West Art History Tour

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Food & Walking Tours, Historical Tours, Key West, Tour Reviews, Tours, Walking Tours

Key West: History and Culture Southernmost Walking Tour

/ June 8, 2026

11.Key West: History and Culture Southernmost Walking Tour

A 90-minute Key West walk with a local guide, stories behind shipwrecking, sponges, and cigars, ending at the Southernmost Point buoy.

★ 4.9

25 reviews1.5 hoursFrom $39by Florida Keys Ventures

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Food, Food & Drink, Food & Walking Tours, Historical Tours, Key West, Private, Tour Reviews, Tours

Key West Historic Private Food Tour with 5 Authentic Tastings

/ June 13, 2026

12.Key West Historic Private Food Tour with 5 Authentic Tastings

A 2.5-hour Key West private food tour with 5 tastings, iced coffee, museum and aquarium admissions, and an end at Mallory Square.

★ 5.0

“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!”

11 reviews2 hours 30 minutes (approx.)From $370.00by Secret Food Tours

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Food & Walking Tours, Ghost & Haunted Tours, Historical Tours, Key West, Private, Tour Reviews, Tours, Walking Tours

PRIVATE Key West Haunted History Walking Tour

/ June 13, 2026

13.PRIVATE Key West Haunted History Walking Tour

Private Key West haunted history walking tour with a local guide, haunted mansions and bars, and optional drink stops starting at 7:30 pm.

★ 5.0

“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!”

10 reviewsFrom $137.50by Up The Keys Tours

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Audio Tours, Cruises & Boat Tours, Historical Tours, Key West, Self-Guided Tours, Tour Reviews, Tours

Cruise Through Key West’s Black History Audio Tour

/ June 14, 2026

14.Cruise Through Key West’s Black History Audio Tour

Self-paced Black history audio tour in Key West: Higgs Beach graves, a Union fort, churches, conch salad, and key lime pie for $8.

★ 5.0

“Fun opportunity. There are 18 stops. Best to rent golf cart. Easy to use. Lots of history to learn about on the island. You get to see the AMe Zion church. Teach about the cemetery which is the highest point on the island. Lots of cute things to learn. Clear voice to understand.”

8 reviewsFrom $8by BeachBunny's Original Tours of Key West

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Audio Tours, Food & Walking Tours, Guided, Historical Tours, Key West, Self-Guided Tours, Tour Reviews, Tours, Walking Tours

Key West History Audio Guided Walking Tour

/ June 18, 2026

15.Key West History Audio Guided Walking Tour

Self-guided Key West audio walk from the Custom House. Hear Hemingway, Sloppy Joe’s, Jimmy Buffett spots, and key lime pie lore.

★ 5.0

“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!!”

3 reviews1 hour to 1 hour 30 minutes (approx.)From $9.75by WalknTours

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Historical Tours

15 Best Historical Tours In Key West