10 Tours in Key West That You Shouldn't Miss

March 6, 2022 Darleen Reid

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. Guided Bicycle Tour of Old Town Key West

122 Ann St, Key West, FL 33040, USA Key Lime Bike Tours
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4.9 based on 1,149 reviews

Cruising the best of Old Key West! Come join a local guide on a leisurely 3 hour tour of Old Town Key West. You'll learn the history of the "Conch Republic", and see all the sights. Ride your comfortable single speed beach cruiser to Mallory Square, Mile Marker Zero, Ernest Hemingway's home, the Southernmost Point in the Continental USA, and more. To finish it off we'll have a slice of Key West's iconic dessert, Key Lime Pie. Bicycle, helmets, and a 16 ounce (1/2 liter) bottle of water provided. Come see why we're the #1 rated thing to do in Key West!

Inclusions: Bottled water, Snacks (Key Lime Pie), Snacks

Exclusions: Gratuities

Reviewed By denise850256

We had a great time- fun guide and great group. Such a great way to see Key West and hear really interesting stories from a local perspective.

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

Garbo's Grill @ Hanks!, 409 Caroline St, Key West, FL 33040, USA Key West Food Tours
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4.9 based on 209 reviews

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood options) cuban sandwich & key lime pie tastings. Sample classic ingredients like Key West pink shrimp, Caribbean warm-water lobster, and fresh fish. Sip white wine after walking through the tropical neighborhood streets. This small-group tour is limited to 10 people, and you'll leave with a greater understanding of the industries that shaped our island and culture. Joining a fish lover, but not one yourself? No problem, we’ve got you covered with equally delicious substitutions.

Inclusions: Food or drink tastings at 5 locations, Walking tour of downtown Key West, Professionally-trained local guide, Exclusive coupons & recipes, Water is included at most stops, Seafood substitutes include pork & beef, if this is a problem, please consider another of our tours.

Exclusions: Hotel pickup and drop-off, Gratuities, We are unable to accommodate vegetarians/vegans. Only Fish, shellfish, dairy, gluten & nut allergies

Reviewed By O4760FYalanm

Beginning with our introduction to Cuban food at El Siboney, a cool tropical drink at the Rum Bar and ending with Cuban Coffee at the Cuban Coffee Queen Roasters the tour was thoroughly enjoyable. Our guide, Meredith, did a wonderful job at each food/beverage stop as well as some stops in between, giving us explanations of the history and cultural events that made Key West what it is today. From the Cigar factory that is now home to the Health Department to the reason there are free range chickens all over town, we learned a lot more about the town than we expected on a food tour. It was well worth it.

3. Shark and Wildlife Viewing Adventure in Key West

Opal Key Resort & Marina, 245 Front St, Key West, FL 33040, USA Key West Extreme Adventures Shark Tours
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4.9 based on 559 reviews

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to view the sharks. Delight in close-up views of sharks and a variety of other marine life. In this eco-friendly catamaran, travel through shallow waters to a location a few miles from shore, observing dolphins, stingrays, barracudas and native birds along the way. Bait is used to attract lemon, nurse and other types of sharks to the side of the boat. Learn all about Key West wildlife and enjoy complimentary soda, juice and chips throughout this family-friendly tour. In order to adhere to recommended guidelines we are limited to 20 passengers per trip during these difficult times. In order for us to control the number of passengers, you must call KWEA in advance for bookings. We do have rates for private tours for families. We're taking every precaution and the boat is sanitized after every tour.

Inclusions: Professional guide, Use of polarized sunglasses, Soda and juice, Chips, Bottled water

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By 93shariu

Wonderful experience! Captain Dave & Captain Clay are very knowledgeable about the ocean and its inhabitants. We learned a lot and had a very enjoyable morning. Other tour captains were asking where the dolphin pod we found was, since Captain Clay is well known for spotting them. Watching the sharks eat the bait is both fascinating and terrifying at the same time

4. Small-Group Key West Sunset Sail with Wine

255 Front St, Key West, FL 33040, USA Danger Charters
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4.9 based on 343 reviews

Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening or just to enjoy time with friends. Please arrive 30 minutes prior to your departure to check in.

Inclusions: Unlimited beer, wine and soft drinks, Wine tasting, Light refreshments

Exclusions: Gratuities

Reviewed By laurenl698

We had originally planned to do the Dry Tortugas, but it was sold out for our dates. Danger Charters was recommended by our hotel. While we were originally disappointed not to be heading to the Dry Tortugas, I’m so glad we ended up with Danger!! The crew, Capt. Kevin, Dave & Meg were fantastic making sure everyone on board was having a great trip. The snorkeling spot off Cottrell Key was one of the best I’ve seen. Meg pointed out turtles, a sleeping nurse shark among a ton of sting rays and other bright fish and turtles. Next stop was lunch on a beautiful teal blue sandy bottom sand bar. Drinks were flowing for those that wanted the pirate life, while kayak adventures were on hand for the nature enthusiasts. Highly recommended for a first time snorkeler to the more experienced. We will definitely be back to check out their other tours!!

5. Adults only Champagne Celebration Sunset Cruise from Key West

201 Margaret St, Key West, FL 33040, USA Catamaran Echo
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4.9 based on 293 reviews

Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included in the tour price are the house champagne Chandon Brut, 7 premium red and white still wines, 3 kinds of ice-cold beers and a champagne-inspired Gourmet Cheese Buffet (naturally gluten free) that includes 4 international cheeses, amazing big berry tray, local smoked fish dip, a selection of crisps and fresh-baked crusty bread. Two other Moët & Chandon champagnes are available for additional purchase - both at wholesale price for guests. Key West is famous for its sunset, and there’s no better way to watch it than on the Champagne Celebration Sunset Cruise. This trip now limited to adult 10 passengers on a 28 person sailing catamaran, for comfortable social distancing.

Inclusions: 2-hour sunset cruise, Champagne-inspired gourmet cheese buffet, Domain Chandon Brut Classic Champagne (additional champagne upgrades available), Ice-cold beers (domestic and imported), An international selection of premium wines, Local taxes

Exclusions: Gratuities, Moët & Chandon Imperial (White Star) champagne and Moët & Chandon Rose Imperial champagne (additional fee)

Reviewed By JohnB5570

We took our third trip with Echo and as always a great time. Crew is great! Friendly. Nice, they tell you about in detail the champagne, wines and cheese. Next visit we will do again

6. Key West Mangrove Kayak Eco Tour

Lazy Dog Adventures, 5114 Overseas Hwy, Key West, FL 33040, USA Lazy Dog Adventures
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4.9 based on 520 reviews

Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West. You will glide through the winding mangrove creeks and paddle through inches of water, where you can easily view and learn about the geological structure of the Keys along with its inhabitants, all from the comfort of your kayak. Your adventure will give you a chance to view the mangrove environment up close, along with its marine life including tropical fish, crabs, sea stars, jellyfish, sea cucumbers, sponges and various aquatic birds. Every trip leads us on a different adventure!

Inclusions: Local Guide, Quiet side of Key West

Exclusions: Bottled water available for sale, Dry bags available for rent, Gratuities, Hotel Pick Up

Reviewed By stephobr

This was a great tour. Perfect length of time and very interesting. Lindsey was an excellent tour guide and we learned a lot from her. We got to see a manatee, nurse shark, starfish and live conch. So much fun! Definitely wear a hat and sun shirt as the rays can be brutal out in the open. Highly recommend this tour!

7. Half-Day Cruise from Key West with Kayaking and Snorkeling

255 Front St, Key West, FL 33040, USA Danger Charters
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4.9 based on 599 reviews

Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys. You'll cruise out to a mangrove eco-system to kayak through shallow waters, home to a wide variety of birds, and then you'll have the opportunity to snorkel in the clear sea. Snacks, beer, wine, and use of equipment are included. Select a morning or afternoon tour when booking. Please arrive 30 minutes prior to your departure to check in.

Inclusions: Light refreshments, Unlimited beer, wine and soft drinks, Professional guide, Use of Snorkelling equipment

Exclusions: Gratuities, Towels, Hotel pickup and drop-off

Reviewed By Michelle L

Great guides, wine tasting & quick bites was perfect. We would absolutely do it again. You won’t regret this tour.

8. Key West Southernmost Food and Cultural Walking Tour

El Siboney Restaurant (Downtown), 900 Catherine St, Key West, FL 33040, USA Key West Food Tours
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4.9 based on 467 reviews

Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 4 locally-run “mom and pop” establishments in historic old town, dining on typical Cuban dishes, local seafood, and of course -- Key Lime Pie. Food samples are enough for a hearty lunch. Between tastings walk like a local, away from the touristy streets, as your guide shares insights about city history, food and architecture. This is a small-group tour, with a maximum of 10 people, ensuring a personalized experience.

Inclusions: 4 Food tastings & 1 alcoholic beverage - totaling a hearty lunch, Walking tour of Key West's Old Town covering 1.2 miles, Friendly & knowledgeable local guide, Exclusive in-store coupons, Water included at every stop

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By daljindern2019

This was a fantastic food tour! I felt like we were in good hands with our tour guide Dana, who was very knowledgeable and seemed very passionate about the topic. We enjoyed her sense of humor. The food choices seemed well thought out and were amazing. I highly recommend this tour!

9. Sunset Sail in Key West with Beverages Included

Hyatt Centric Key West Resort & Spa, 601 Front St, Key West, FL 33040, USA Floridays
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4.9 based on 178 reviews

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the water for a Key West sunset is like being IN the sunset itself. There is nothing quite like it. Who knows, you may get lucky enough to witness that elusive green flash!

Inclusions: Restroom on board, Champagne, flavored mimosas, white wine, margaritas, selection of craft beers, Bottled water, Soda/Pop

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Reviewed By RamonaF541

I booked this trip due to the smallness of the group and am also a sailboat fanatic. This turned out to be fabulous, and much more intimate than the large catamaran trips. It was nice to be snorkeling without hoards of people flailing around you. The staff was engaging and fun, and kept us happy with beverages after fun in the water. I highly recommend Floridays and also recommend the afternoon tour as the reef is not busy with large catamaran groups. Thank you Floridays for a splendid afternoon!

10. Key West Sunset Sail Aboard Schooner

202 William St, Key West, FL 33040, USA Classic Harbor Line
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4.8 based on 235 reviews

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.

Inclusions: Your 2-hour sailing experience aboard America 2.0, Complimentary beer, wine, Champagne and soda , Individually plated hors d'oeuvres

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By fox151515

This was a great experience in Key West. The crew was very friendly and attentive, basically as many drinks as you wanted (beer, wine, soft drinks, think you may pay extra for champagne but not sure). The snacks were simple but hit the mark. Very friendly atmosphere, everyone talkative sitting around us. Two hours was just right on the water. Don't worry about standing in line early to get a good spot, they have assigned seats when you board so waiting in line serves no purpose--just don't be late for departure! Well run operation, would do it again!

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