The 10 Best Outdoor Activities in Key West, Florida (FL)

November 3, 2021 Jacquiline Darosa

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. AWS Charters, Key West Flats Fishing

Excellent
99%
Good
1%
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5.0 based on 225 reviews

AWS Charters, Key West Flats Fishing

Spend a relaxing day in the beautiful backcountry off of Key west. You can either go on a 16ft flats skiff chasing tarpon, bonefish, permit and sharks or take out the 23ft Hurricane deck boat and have a custom made trip for up to 6 people.

2. Danger Charters

Excellent
92%
Good
5%
Satisfactory
1%
Poor
1%
Terrible
1%
Overall Ratings

5.0 based on 5,355 reviews

Danger Charters

When you sail with Danger Charters, you sail to another world and time; to a place where the wildlife is still "wild" and your interaction with nature is intimate and authentic. You feel as if you've stepped back in time, back to the days when the Florida Keys backcountry was home to traditional, shallow-draft sailing craft, captained by local water men who had grown up sailing and navigating the notorious shallows and challenging narrow channels of the Florida Keys.

3. Catamaran Echo

Excellent
91%
Good
6%
Satisfactory
2%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 1,712 reviews

Catamaran Echo

Wild Dolphin & Shallow Water Snorkel day trips - Champagne Celebration Sunset Sailing - Private Charters too! It's always upscale on this beautiful 28 seat sailing catamaran because of quality controls, and limiting public day and sunset trips to only 10 passengers max for healthy social distancing onboard. On the Wild Dolphin Sail and Shallow Snorkel trips, explore reefs, wrecks and giant sponge gardens (wherever it's best) and enjoy some great Sailing too. Every day they visit the local Wild Dolphins in their natural habitat. Top quality snacks, fruit, soft drinks, beers and wines are always included free on Catamaran Echo. The adults only Champagne Celebration Sunset Cruise includes only the best of the best served on the water - Chandon Champagne, 7 premium Wines, 3 top Beers and our famous Gourmet Cheese Buffet. Even better - Moet & Chandon Champagnes are available as an upgrade, and at wholesale prices. You deserve to be served the best, while sailing into the Key West sunset.

4. Honest Eco

Excellent
97%
Good
3%
Satisfactory
0%
Poor
0%
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Overall Ratings

5.0 based on 1,645 reviews

Honest Eco

Dolphin Watch - The Key West Original... Since 1986! Book Direct and support our local ecosystem! Join us to Watch Dolphins and Snorkel on our catamaran SQUID. The boat conveniently departs from the Historic Seaport in Old Town Key West and has many features that set her apart. • Small Groups • 37' length x 14' width • 4 Hour Long Trip on a Quick Power Boat helps us consistently find Dolphins • Guaranteed Dolphin Sightings or Your Next Trip is Free. • 30 Years of Helping our Guests Experience Wild Dolphins Our trip focuses on delivering the best dolphin watching and snorkeling experience possible for our guests. We do this through the combination of our listed features and the passion and knowledge of our Captains. • Snorkel Gear and Instruction provided • Fresh Fruit and Water • Guided Snorkeling! Your Captain will join you for the Snorkel. • Bathroom and Freshwater Shower • Wet suits for winter months • Calm snorkel Locations.

5. Breezin Sailing Charters

Excellent
100%
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5.0 based on 219 reviews

Breezin Sailing Charters

Breezin the Keys with Captain Dees - Private sailing charters, sailing lessons, snorkeling, weddings and memorials. Learn the fundamentals of sailing! Or just sit back, relax and enjoy a beautiful Catalina 42 foot sailboat.

6. Schooner Spirit of Independence

Excellent
98%
Good
1%
Satisfactory
0%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 661 reviews

Schooner Spirit of Independence

We're sailing out of Key West bringing a lifetime of History and Adventure aboard. The focus will be a fun safe unforgettable sail. Sail Key West with us on a ship builder's masterpiece the Spirit of Independence. Sunset Sails, also available for special events.

7. All In Fishing Charters

Excellent
100%
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0%
Satisfactory
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5.0 based on 121 reviews

All In Fishing Charters

"All In" Is a private fishing charter business that is owner operated here in Key West Florida. Captain Garrett Frey is well versed in the waters around Key West. Operating on a fully redone spotless 29 foot Sea Vee. We stand by and offer a no fish no pay policy.

8. Floridays

Excellent
94%
Good
3%
Satisfactory
1%
Poor
0%
Terrible
2%
Overall Ratings

5.0 based on 874 reviews

Floridays

Floridays is a beautiful 54' sailing yacht in Key West, Florida offering morning breakfast sails, daily snorkeling trips to the reef and champagne sunset sails. Our experienced captains and crew along with our limited passenger count will assure you of a unique and delightful trip. Avoid the crowds, come sail with us! All snorkeling gear is provided for the reef trips and complimentary beverages are served while on board including water, sodas, craft beer, white wine, margaritas and of course champagne for the sunset sail. Floridays is also available for private charter for your wedding, group activity or just an individual family day on the water. Before booking, please call for more information including seasonal interruptions, trip availability and weather conditions.

9. Lazy Dog Adventures

Excellent
89%
Good
9%
Satisfactory
2%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 1,703 reviews

Lazy Dog Adventures

We have kayak and stand up paddleboard tours and rentals and back country boat tours all led by our experienced guides and staff. Let us help you explore the quiet side of Key West. We're surrounded by warm, shallow waters. You can glide over sea grass beds and in and out of a protected mangrove eco-system. An abundance of fish and birds surround us!

10. Key West Extreme Adventures Shark Tours

Excellent
94%
Good
5%
Satisfactory
1%
Poor
0%
Terrible
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Overall Ratings

5.0 based on 810 reviews

Key West Extreme Adventures Shark Tours

Enjoy a shark and wildlife eco-tour in Key West aboard the custom built eco-adventure vessel 'Tiger Cat'. You'll cruise to the pristine backcountry waters for two hours of shark and wildlife viewing. A scent is deployed to attract these apex predators right next to the boat. In these calm waters you will see a variety of wildlife, turtles, stingrays, birds and dolphins. Local wildlife experts conduct the tour. Our success rate for seeing sharks is 99%. Our success rate for seeing Dolphin is 90%. As for the other wildlife, it's different every trip. This is a safe and exciting adventure for all ages.

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