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Top 9 Best Key West Tours for Discovering its History and Culture

by Roslie

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Planning the ultimate Key West itinerary and looking for the best Key West tours? The opportunities for fun and adventure on this island paradise are unlimited. There are so many awesome things to do in the Florida Keys, and Key West is filled to the brim with history and culture just waiting to be discovered.

We’ve put together this list of the best Key West tours for discovering its vibrant culture and heritage. From bicycle tours to ghost tours, foodie tours to pub crawls, there’s something for everyone’s sense of fun.


Please keep in mind these details are subject to change. Due to COVID-19, social distancing and face coverings may be required. Be sure to check local health officials’ safety regulations and each establishment’s website for updated information before making final plans.

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Things to Do in Key West Florida: Best Tours

1. Key West Old Town Trolley Hop-On Hop-Off Tour

Key West Hop On Hop Off Bus Tour

If you don’t like to feel rushed when sightseeing, this 12 stop trolley tour allows you to explore Key West at your own pace. Whether you want to take your time soaking in the culture, packing in as much sightseeing as you can into one day in Key West, the hop-on, hop-off tour takes you on a route of more than 100 points of interest.

A friendly tour guide will provide an insider scoop on the history of Key West as you go. The ticket is valid all day, and the trolley picks up regularly at the stops so that you can easily continue on your adventure. And as a bonus, each tour ticket includes admission to the Sails to Rails Museum.

Why I love this tour:

  • It’s a whole day of fun
  • You can explore this amazing island at your own pace
  • It takes you to all of the best shopping and dining locations in the city

2. Key West Southernmost Food and Cultural Walking Tour

DJs Clam Shack Lobster Roll, Key West, Florida

This guided walking tour is one of the best Key West tours – as it combines learning the history and culture of the island with great local food.

As you meander through the colorful Key West, your friendly tour guide will share stories about the island’s fascinating past, as well as visit locals’ favored hole-in-the-wall spots for samplings of the Cuban and Caribbean influences on Key West food and culture.

Why I love this tour:

  • You get to sample some seriously delicious food where locals frequent
  • It gives you an inside look at the culture of this island
  • It teaches you about the rich history of the city

3. Key West History and Culture Southernmost Walking Tour

Key West Southernmost Point

This walking tour takes participants on an adventure through the streets of Key West, while a friendly and knowledgeable tour guide lets you in on the secrets and stories of the island’s history. You’ll learn about the island’s wealthy past and industries throughout the years.

The tour concludes at the southernmost point buoy. This tour takes about an hour and a half and at a comfortable strolling pace, but sunscreen like this and comfortable shoes are strongly recommended!

Why I love this tour:

  • You get to learn so much about the island’s rich history
  • It’s a great photo op!
  • You get to experience Key West through the eyes of a local

4. Key West Guided Bicycle Tour with Key Lime Pie

Duval Street Key West Florida

Bike riding through Key West is one of the best ways to experience the city from a local’s perspective. On this 3-hour bicycle adventure, you’ll roll around the colorful island with a knowledgeable guide in tow, recalling the fascinating history of Old Town District, Mile Marker Zero, Higgs Beach, and various other landmarks.

You’ll have plenty of photo opportunities along the way, ending your bicycle island excursion with a piece of the traditional key lime pie.

Why I love this tour:

  • Cruising on a bicycle is a great way to see a different side of the island 
  • Some awesome photo ops!
  • The tour guides are funny, and they know the island’s history well.

5. Key West Conch Train Tour

Key West Florida Conch Train Tour

All aboard! This delightful train ride will take you on a trip around Key Wests’ Old Town stopping at a variety of historical landmarks while hearing fascinating stories about pirates and sunken treasures.

This one-and-a-half-hour tour includes stops that will take you to the top of the Key West Shipwreck observation tower, see Hemingway’s house, and enjoy the excellent shopping and dining amid Duval Street.

Why I love this tour:

  • It turns you into a happy little kid
  • It’s both fun and educational
  • You get to explore one of the coolest parts of Key West

6. Key West Bone Island Haunted Pub Crawl

Captain Tony's Saloon Haunted Bar in Key West Florida

If you like getting spooked out, you’ll be glad to know that there’s a bit of a scary side to Key West that’s because the island has been named one of the top five most haunted cities in the USA. 

Key West is also known as “Bone Island” because of its seriously spooky history.

On this combination ghost tour and pub crawl, your “ghost host” will take you to visit three haunted pubs in Old Town. You’ll get chills as you listen to tales of cursed treasure, voodoo, and unexplained deaths. 

Which of the stories are true and which are fake? Nobody knows, and that’s what leaves you spooked.

Why I love this tour:

  • It’s pretty fun to get chills up your spine
  • You get to see a different side of Key West at night
  • Souvenir t-shirt included

7. Ghosts & Gravestones Tour of Key West

Key West Ghost & Gravestones Tour

One of the most popular things to do in Key West is to join a ghost tour like the Ghost & Gravestones. Jump aboard the trolley of the doomed, and travel the dark streets of Old Town, visiting Key West’s supernatural history.

Intrigued by Key West’s haunted history? Check out these 10 spooky things to do in Key West.

Why I love this tour:

  • It’s highly entertaining and gets you involved in the fun
  • It lets you see a different side of the city from what you’d expect
  • It’s a bit bone-chilling

8. Key West Craft Cocktail Crawl

Key West for a Day 11 Hot Spots You Do Not Want to Miss - The Rum Bar

Key West’s unique and eclectic bar scene makes it a great place to discover hidden gems. The island has a famously rowdy bar scene, and the Key West Cocktail Crawl tour allows participants to experience the city from a local’s perspective as they venture to local watering holes to enjoy craft cocktails.

As you journey around the island (and maybe get a little tipsy), your guide will fill you in on fun tidbits on the history and culture of this quirky city.

Why I love this tour:

  • You get to explore local favored spots
  • It’s a fun way to explore the island
  • You get to try some excellent food as well, two food samplings also included.

9. Key West Historic Seaport Food Tasting and Cultural Walking Tour

Blond Giraffe Key Lime Pie Factory Tavernier, Florida

If you love seafood, this foodie walking tour is for you. Stroll through Key West’s colorful neighborhoods and beaches with a small group and a friendly guide, with regular stops to try the delightful seafood cuisine the island is so well known for.

You’ll stop at five different locations, learning about Key West’s history and culture as you go. You’ll get to sample dishes such as conch salad, Key West pink shrimp, and the ever-so-famous slice of key lime pie!

Why I love this tour:

  • It’s an opportunity to eat your way around this island
  • So much good food!
  • It’s a relaxing stroll that doesn’t take much energy.

Best Key West Tour for You?

I hope you’ve gotten some inspiration from this with great things to do in Key West. Whether your idea of island fun is riding a miniature train, or partying at the bars in town, or participating in a ghost tour, there’s something on this list that everyone will enjoy. 

So, which of these Key West tours will you add to your itinerary?

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