10 Private Tours in Florida Keys That You Shouldn't Miss

March 4, 2022 Darwin Bolte

Stretching 126 miles south toward Cuba, the stunning Keys are a perfect escape. Highlights along the way include Key Largo, Islamorada, Marathon, Big Pine Key and the irrepressible Key West. Get up close with an amazing array of fish while snorkeling, diving or fishing in the warm turquoise waters. Creeks, coral and costumed spectacles are other lures along the way. Highway 1 is a spectacular ribbon tying together the islands and atolls of this paradise between the Gulf of Mexico and the Atlantic.
Restaurants in Florida Keys

1. Private Tour of Florida Keys from Key West: 7-Mile Bridge, Beach, and Key Deer

Up The Keys
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5.0 based on 8 reviews

Private, exclusive tour of the islands near Key West. The only land-based tour in the Florida Keys, operating from Key West. Small groups of up to 12 travel in a comfortable customized air-conditioned vehicle along the Overseas Highway. Drivers are professional tour guides who share fun and interesting information about the Florida Keys and the islands we traverse. Experience the iconic 7-Mile Bridge, relax on the world-famous Bahia Honda Beach, and photograph endangered Key Deer on Big Pine Key. Children are welcome. This tour is customizable. You'll love this tour so much, you'll book it again next year!

Inclusions: Variety of sandwiches & chips, water & sodas, Entry Fees, Air-conditioned vehicle, Hotel Pick-Up

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Reviewed By N7806XTaaronj

The Tour Guide (Rick) was personally, knowable and very informative about Key West. He asked us what were some of our interests and incorporated in the tour. He advised us that we could stop at any point on the tour if we had a need.

2. Kayak Tour of Mangrove Maze from Key West

5016 5th Ave, Key West, FL 33040, USA Blue Moon Kayak Key West
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5.0 based on 20 reviews

On this Tour you will paddle through three different bodies of water; The Gulf of Mexico, Cow Key Channel and into the Mangrove Mazes to get into the Salt ponds of Key West. Our Tour guides will share the History of Key West and South Florida, educate you on the flora and fauna that you may encounter and see throughout the tour and discuss how to become more sustainable in today's world.

Inclusions: Coconut Water, Kayaks, Life Jackets, Paddles, Whistles

Exclusions: Gratuities

Reviewed By Njchutz

Bluemoon kayak is the best! Awesome staff, great tour and we were able to clean up two bags of garbage. Highly recommend the kayak mangrove/Waterway clean up tour - this is exactly what tourist activities should be all about! Tons of education while making this place a little bit cleaner. Joe is a badass! Crabs, snapper, tarpon and about 50 lbs less of garbage plugging up cow key channel. Highly recommend!

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
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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. Private Day Trip - A Self-Guided Drive Through the Lower Keys

Stock Island, FL 33040, USA BeachBunny's Original Tours of Key West
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5.0 based on 3 reviews

Turn your phone or tablet into a local tour guide! Download this GPS-driven audio & multimedia tour, and as you drive from Key West to Marathon (CAR RENTAL/DRIVER NOT INCLUDED) your phone or device alerts you to great places to stop. Enable audio narration to hear about each point of interest as you approach the area. You’ll have historic photos, a map linked to your GPS, and websites and restaurant menus at your fingertips. There’s so much to see and do in just one-and-a-half hours of driving from Key West to Marathon. Visit the Keys’ most beautiful natural sand beach, tan on a secret nude beach, check out a limestone quarry inhabited by American alligators, spot rare Key deer, find the Keys’ best shrimp pizza, and jump off an abandoned bridge into a cool-water canal. After purchasing, check your confirmation emails for instructions on how to download your tour.

Inclusions: Historic photos , Restaurant menus

Exclusions: Vehicle and driver , 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. 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.

6. 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.

7. 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!!!!

8. 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
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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.

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. 4-Hour Private Sand Bar Cruise on a Boat in Key West

Garrison Bight Marina, 711 Eisenhower Dr, Key West, FL 33040, USA Sunshine Charters
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5.0 based on 2 reviews

Our private cruise to the sandbars will allow you to choose from a private sandbar. With over 2 hours on the sandbars you can visit more if you like.

Inclusions: Water, Ice and sunscreen.

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