What to do and see in Key West, Florida (FL): The Best Walking Tours

November 24, 2021 Milan Banda

Does time ever pass in the Florida Keys? Everyone and everything in Key West seems to go at its own pace, right down to the ice melting slooooowly in your margarita glass. Of course, it’s not all limes and leisure – Key West is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and the island has been home to literary greats like Ernest Hemingway and Tennessee Williams. The diving here is phenomenal, as is the kid-friendly Florida Keys Eco-Discovery Center.
Restaurants in Key West

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

107 Fitzpatrick St, Key West, FL 33040, USA Florida Keys Ventures
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5.0 based on 41 reviews

Join us for a 1.5-hour adventure! Our tour is led by knowledgeable local guides. As we walk through the streets of Key West’s old town, you will discover the history and culture of our island. Shipwrecking, sponging, cigar manufacturing, treasure hunting - it’s all about Key West! What to bring: Hat, sunglasses, and sunblock is a must. Bring at least one bottle of water for yourself. Wear comfortable clothing and shoes. Sneakers are the best option. Camera or your phone to take pictures. Your adventurous spirit :)

Inclusions: Local Guide

Exclusions: Gratuities

Reviewed By mtdocVa

AJ gave us a very informative and interesting tour of historic Key West. He used a large i-pad to show historic photos of the sites we were standing in front of which reinforced the information he was tell us. He's very knowledgeable about the area and we thoroughly enjoyed our walk and talk. My wife and I highly recommend this tour.

2. Key West Marriage Proposal Package

Smathers Beach, 2601 S Roosevelt Blvd, Key West, FL 33040, USA Romantic Events
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5.0 based on 13 reviews

The romantic adventure service, “Romantic Events LLC” is designed to organize the most important events in your life, leaving you the opportunity to improvise and play the main role in them, and then leave them in your memory forever

Inclusions: We provide all romantic equipment , We provide deserts, bottle of champagne, fruits

Exclusions: We are not provide alcoholic Beverages

Reviewed By _X7363EP

Great attention to my needs and event details. Very friendly stuff! Very creative decorations.Great company, they know what they doing. Highly recommended!!!

3. Key West Historic District Small-Group Walking Tour

716 Duval St, Key West, FL 33040, USA Florida Keys Ventures
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5.0 based on 15 reviews

You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.

Inclusions: Local Guide

Exclusions: Gratuities, Bottled water, Lunch

Reviewed By ACuneo87

Enough can not be said for AJ’s tour throughout the historic old city of Key West. Having read up on Key west culture before I went, I knew there would be lots to see and do but AJ’s tour was the best way of condensing all these must see places into one lovely afternoon. Not only was his abundance of knowledge so impressive but his delivery and delightful attitude made for a fun and refreshing approach to all the history of key West!! I would definitely recommend this tour to anyone wanting to get a crash course in key west history!! You will not be disappointed that’s for sure!!!

4. Easy Stroll Audio Tour Downtown Key West

Mallory Square, 400 Wall St, Key West, FL 33040, USA BeachBunny's Original Tours of Key West
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5.0 based on 2 reviews

Turn your phone or tablet into a local tour guide! Download this GPS-driven audio & multimedia tour to your phone or tablet. Enable audio narration that starts as you near each point or interest, or read about stop. Local knowledge, historic photos, and links to websites and restaurant menus rest at your fingertips. In just 1 hour of walking, learn the history, culture, and cuisine of Key West. Never waste a step following this route. Visit the most important museums and attractions. Discover the island’s best Key lime pie, Cuban cigars, rum mojitos, craft beer, conch ceviche, fish tacos, and handmade sandals. Learn about famous writers, wreckers, and pirates. End with a swim on a popular beach. Perfect for solo travelers and small groups. Sight-see at your own pace, avoid being herded in a big crowd and only linger in the places that truly interest you. After purchasing, check your confirmation emails for instructions on how to download your tour.

Inclusions: historic photos and videos, restaurant menus

Exclusions: Lunch, Snacks, Alcoholic Beverages, Parking Fees

Reviewed By F2308OBaprilg

A very informative tour. Easy to understand, good directions, and plenty of ideas for more activities to do! Self guided gave us the flexibility to stay as long as we wanted at each stop.

5. Self-Guided Audio Sunset Stroll in Key West

Dante's Key West Pool Bar & Restaurant, 955 Caroline St, Key West, FL 33040, USA BeachBunny's Original Tours of Key West
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5.0 based on 1 reviews

Turn your phone or tablet into a local tour guide! Download this multi-media, GPS-driven tour to enjoy historic photos, recordings and videos plus links to restaurant menus and websites at your fingertips. Stroll along the Gulf of Mexico, enjoying the island’s best happy hours, then watch the famous Key West sunset. In just 35 minutes of walking, you can cool off at a tiki bar with a gorgeous waterfall, then stroll along a hidden boardwalk with stunning ocean views. Find the best best happy hours with the tastiest seafood snacks. Stroll past Jimmy Buffett’s secret recording studio. Enjoy Key West’s most popular brewery, best mojito, or the world’s yummiest coffee. Learn where locals watch the sunset. Sight-see at your own pace, avoid being herded in a crowd, and linger only in the places that truly interest you. After purchasing, check your confirmation emails for instructions on how to download your tour.

Inclusions: Historic photos , Happy Hour Menus

Exclusions: Alcoholic Beverages

Reviewed By F2308OBaprilg

A very informative tour. Easy to understand, good directions, and plenty of ideas for more activities to do! Self guided gave us the flexibility to stay as long as we wanted at each stop.

6. Private Highlights and Stories of Key West Walking Tour

Mel Fisher Maritime Museum, 200 Greene St, Key West, FL 33040, USA Hidden Key West Walking Tours
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5.0 based on 5 reviews

Key West Highlights and Stories Private Tour- “2020 WINNER Best Key West Walking Tour" Join Key West's unofficial "mayor" on a wonderful 2.5 hour private stroll through the historic Old Town streets. Our goal is for you to have fun while enjoying the rich and colorful history, legends, points of interest, and culture that make Old Town Key West unique and famous across the globe. The quality of our tours and our guides is unmatched on the island. With unique insights and carefully crafted tour routes, we strive to provide the best walking tours available in Key West. *Consistently ranked as the top “Highlights Tour” by Keys Tourism Association *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to sharing Old Town Key West with you.

Inclusions: Full list of our favorite restaurant recommendations, Professional, friendly, and highly trained local guide, Rain Ponchos are provided if it's raining

Exclusions: Hotel pickup and drop-off, Umbrellas if it is raining (rain ponchos are provided), Alcoholic beverages are usually available for purchase before, during, and after the tour, We suggest you bring at least one bottle of water

Reviewed By B5018NEsusanc

We always try to take a walking tour early on during a trip to a new place. This one did not disappoint. Richard was very knowledgeable and friendly and gave us a good overview of the town. He also shared many fascinating stories about Key West and it’s history and present as well. I highly recommend!!!!

7. The Original Key West Ghost Hunt

301 Whitehead St, Key West, FL 33040, USA Key West Ghost Hunt
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5.0 based on 7 reviews

We are the only locally owned haunted attraction with exclusive access to two locations. Our local experts provide Ghost Hunting equipment along with personal experience that can't be replicated.

Inclusions: Use of Ghost Hunting equipment such as Dowsing Rods, EMF meters, a spirit board, and more!

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Reviewed By StaceyF593

This was the most interesting ghost tour I have ever been on. The stories seemed like you were there. I felt a real sense of the paranormal activity.

8. Hemingway in Key West Tours- 2 Hour Guided Walking Tour

The Ernest Hemingway Home and Museum, 907 Whitehead St, Key West, FL 33040, USA Hemingway in Key West Tours
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5.0 based on 3 reviews

This 2 hour guided tour begins by meeting at the front gate of the Hemingway House. A food sampling will follow, and then a guided tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, his first apartment in Key West where he finished writing “A Farewell to Arms”. Then you will have another food sampling, before visiting where he took the train, fished and charted boats in the Key West Harbor, and finally where he spent a lot of time drinking- Sloppy Joes (the original and the second one). Numerous other historical sites that Hemingway frequented while he lived in Key West will also be visited on this incredible authentic tour.

Inclusions: Lunch, Snacks, Alcoholic Beverages

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9. Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

201 William St, Key West, FL 33040, USA Salty Seaweed Tours
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5.0 based on 4 reviews

We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Learn about how Old Fisherman’s Wharf has transformed into Yacht Harbor! Sit at the bar Mel Fisher did while his treasure sat out front, on display, in the trunk of his car! Open your ears to live music and island vibes as you cocktail into World Famous Mallory Square’s Sunset Celebration!

Inclusions: For Adults *Cocktails at three (3) restaurants & Craft Beer at one (1) restaurant*, For Youth and Adults *Food taste at three (3) restaurants*, Gratuities/Tips for Bartenders

Exclusions: Gratuities/Tips for Tour Guide

Reviewed By BtheMNGR

Tour guide was knowledgeable and knew a lot about what the area used to look like! Cocktails were amazing, great to be able to try out different places! To cap it off with the sunset was just a cherry on top!

10. Key West Historic Homes and Island History - Small Group Walking Tour

Mel Fisher Maritime Museum, 200 Greene St, Key West, FL 33040, USA Hidden Key West Walking Tours
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5.0 based on 48 reviews

Historic Homes & Stories of Key West- "2020 WINNER- Best Key West History Tour" Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you'll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community. We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There's something for everyone to enjoy on this fascinating look behind the scenes of historic Key West. *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to welcoming you and sharing Old Town Key West with you.

Inclusions: Full list of our favorite restaurant recommendations, Professional, friendly, and highly trained local guide, Rain Ponchos are provided if it's raining

Exclusions: Hotel pickup and drop-off, Umbrellas if it is raining (rain ponchos are provided), Alcoholic beverages are usually available for purchase before, during, and after the tour, We suggest you bring at least one bottle of water

Reviewed By B5018NEsusanc

We always try to take a walking tour early on during a trip to a new place. This one did not disappoint. Richard was very knowledgeable and friendly and gave us a good overview of the town. He also shared many fascinating stories about Key West and it’s history and present as well. I highly recommend!!!!

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