Top 10 Boat Tours & Water Sports in Key West, Florida (FL)

March 1, 2022 Tambra Mccollister

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. 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.

2. Easy Day Charters

Excellent
97%
Good
2%
Satisfactory
0%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 571 reviews

Easy Day Charters

Design your own Tropical Adventure! Leave the crowds behind and dissappear into the calm waters surrounding Key West. You choose the activities that interest you - learn something new, focus on your favorite activities or try a little of everything. Special requests welcome!

3. The Schooner Hindu, Hindu Charters

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

5.0 based on 369 reviews

The Schooner Hindu, Hindu Charters

The Schooner Hindu operates in Key West waters from Nov to June The Schooner Hindu operates in Provincetown Ma, from July to Sep TRIPS: 1pm-3pm, 3:pm-5:30pm and a Sunset sail 6:45-8:45 Tickets can be purchased on are website or by calling are booking number.

4. 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.

5. ShadowCaster Flats Fishing

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

5.0 based on 130 reviews

ShadowCaster Flats Fishing

A trip to the Back Country of Key West to catch some of the most sought after fish the ocean has to offer should not be missed. As the owner and operator of the Shadow Caster Capt. John insists on delivering a personalized fishing adventure. With Captain John you can expect Professionalism, Preparation and Performance, qualities that Capt. John has learned from the best in the business and keys to his continued success.

6. AWS Charters, Key West Flats Fishing

Excellent
99%
Good
1%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

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.

7. Honest Eco

Excellent
97%
Good
3%
Satisfactory
0%
Poor
0%
Terrible
0%
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.

8. Venus Charters

Excellent
99%
Good
1%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 235 reviews

Venus Charters

Key West Charter boat with a fun Captain for small groups up to 6. Since 1997 Captain Karen Luknis has been taking adventurers out to see dolphins, do some light tackle fishing, relax on a sandbar with an ice cold beer, do absolutely nothing in the clear turquoise waters surrounding Key West. Private Charters. Special Requests. Pet Friendly. Clothing Optional. Professional. No seasickness. Your wishes can come true!!

9. Dancing Dolphin Spirits Charters with Captain Victoria Impallomeni

Excellent
97%
Good
2%
Satisfactory
1%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 183 reviews

Dancing Dolphin Spirits Charters with Captain Victoria Impallomeni

Gliding over the azure waters of the Florida Keys Wildlife Refuges, called the backcountry, we interact with the wild life especially the birds and dolphins. Teaching environmental marine science while sharing antidotes from my lifetime on these waters creates an atmosphere for conversation. It is my pleasure to help you to understand and appreciate how you can make a difference in the lives of all you see. Visiting in a quiet respectful way, you become one with the life around you. It is a very stress relieving time as you remove any fears and replace them with knowledge as you have a" dolphin day for a human". Enjoy being supported my mother ocean as you snorkel with all of the dolphins friends, the corals, fish and turtles. Explore the hidden pathways inside the mangroves as you experience evolved kayaking which means no paddles, no sunburn, just quiet shaded touring of the many islands surrounding Key West. 44 years of interaction with now 13 generations of dolphin is an honor.

10. 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.

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