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

March 4, 2022 Almeta Stockton

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. Small-group private Key West tour with expert guide

Banana Joe Tours
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 1 reviews

Our Key West tour is carried out by a real tour guide with over 10 years of Florida experience, who will explain everything on the way to Key West and answer all your questions. Of course, we have built in some points on the route where you can leave the van and go on an exploration tour on foot and take pictures. We look forward to seeing you. Your Banana Joe team

Inclusions: Private transportation, Florida expert tour guide, small groups, Insider knowledge

Exclusions:

Reviewed By 540saschag

We loved our Miami City Tour with Hagen! He showed us Miami from a local point of view!! The tour was very informative and engaging. Highly recommended!!

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

107 Fitzpatrick St, Key West, FL 33040, USA Florida Keys Ventures
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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.

3. Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

Flamingo Cafe & Boutique, 716 Duval St, Key West, FL 33040, USA Florida Keys Ventures
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 12 reviews

You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West. First-row, Historic, Cultural and Fun, the only VIP experience tour in Key West. This tour includes a slice of famous Kermit's Key Lime Pie for each of you and a complimentary bottle of water!

Inclusions: Bottled water, Private transportation, Your own private tour guide and driver, Slice Kermits Key Lime Pie

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.

4. Key West Historic District Small-Group Walking Tour

716 Duval St, Key West, FL 33040, USA Florida Keys Ventures
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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!!!

5. Private Walking Tour of Key West

627 Eaton St, Key West, FL 33040, USA Up The Keys
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 6 reviews

Walk through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. **If it's too far or too hot to walk, you have the option of hopping on the Duval Loop bus with your guide for only $1 per person** It's air-conditioned with several convenient stops throughout Old Town. These tours are private so you can ask questions and we can customize the tour to your interests. Your tour guide is knowledgeable about everything Key West, so don't hesitate to let us know what interests you and what you want to know about Key West.

Inclusions: Friendly Knowledgeable Tour Guide

Exclusions:

Reviewed By ajohannes40

We loved this tour. It was so much fun. Indy was absolutely great. Extremely professional, friendly, thorough. We went in the morning and my husband is still raving about this tour (it's now dinner time), the things we saw, and his interactions with Indy. If you can get this tour with Indy, we would highly recommend it.

6. Easy Stroll Audio Tour Downtown Key West

Mallory Square, 400 Wall St, Key West, FL 33040, USA BeachBunny's Original Tours of Key West
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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.

7. 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
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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.

8. 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
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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!!!!

9. 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
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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

Exclusions:

10. Self-Guided Black History Tour of Key West for Electric Car

Mallory Square, Key West, FL 33040, USA BeachBunny's Original Tours of Key West
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 1 reviews

Turn your phone or tablet into a tour guide! Download this GPS-driven audio/media tour, then cruise! Nowhere on this tour will the speed limit exceed 35 mph. ELECTRIC CAR RENTAL IS NOT INCLUDED and must be purchased separately (Some vendors are recommended at the beginning of the tour.) Or sight-see from the comfort of your car, scooter or bike. Drive for one hour, or shop, eat, and swim to spend a whole afternoon immersed in Keys' culture. Learn about Key West's deep ties to the Bahamas and the city's pivotal role defeating the Confederacy. Discover why 250 Africans are buried by the beach, and the surprising spot that was once the island's "blacks only" beach. Visit the island's first black church. Find the Keys' best conch salad, get a taste of Haitian and Cuban flavors and sample Key Lime pie. Historic photos plus links to restaurant menus and websites rest at your fingertips. After purchasing, check confirmation emails for instructions on how to download your tour.

Inclusions: Historic photos , Restaurant menus

Exclusions: Private transportation

Reviewed By mlk7001

We liked that it was self-guided so we were able to go at our own pace. The directions provided by the app we're not accurate. We had to use our GPS for the majority of the ride. It took us about 3 hours, due to our chosen pace and poor directions.

TAGS

Share on FacebookTweet about this on TwitterShare on LinkedInPin on PinterestShare on Google+Email this to someoneShare on VkontakteBookmark

ThingsTodoPost © 2018 - 2024 All rights reserved.