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SAIL AWAY

The Keys Are Calling & We Must Go

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Key West Sailing Charters

What Makes Us Different?

A Danger Charters crew member unties a rope
The bow of a Danger Charters schooner sailing in calm waters in Key West
A young couple drinks champagne and enjoys a sailboat wedding with friends in Key West

What We Provide

Our Playground

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Danger Charters crew member Bradley

On Deck

Bradley

Meet the Crew

Our Fleet

Historic Key West Schooners

Schematic of Danger one of the schooners in Danger Charters' Key West fleet

Danger

Boat Type: 48’ Skipjack
An elegant, custom-built Skipjack replica, Danger perfectly navigates the shallows surrounding the prettiest parts of the Keys.
Schematic of Sarah one of the schooners in Danger Charters' Key West fleet

Sarah

Boat Type: 52’ Exuma
Sarah is an exceptional vessel. She was built for exploring the Keys, Gulf, and Caribbean, and was the first ever Exuma 52!
Schematic of Danger's Prize one of the schooners in Danger Charters' Key West fleet

Danger’s Prize

Boat Type: 52’ Exuma
Commissioned by Danger Charters, Danger’s Prize is spacious, swift, smooth and seamlessly sails in our shallow waters.
Schematic of Pearl one of the schooners in Danger Charters' Key West fleet

Danger’s Pearl

Boat Type: 57’ Rover
Danger’s Pearl is a mini tall ship with romantic-red sails. Her on-deck amenities make her a dream-come-true diving boat.

Learn About Our Boats

Spent my birthday eve sunset sailing with my husband and it was unforgettable! Could not recommend it enough. Such a beautiful time! I would definitely do it again next time we go to Key West. Thank you all for such a wonderful and memorable experience!

Katherine BejeranoGoogle

I can’t get over how personal this experience was!!! The group was small which made the experience that much better. Myself, my sister, and my two daughters had the best time! Everyone was so kind and personable! Thank you for a wonderful time! Danger Charters is definitely a must if you are looking for a sail, snorkel, kayak experience for the first time!

Carlota CastilloGoogle

We did a full day sail and snorkel trip with about 27 of us and it was perfect! The crew Bryan, Logan, and Alex were informative, attentive, down to Earth, and make a mean pasta salad! They even provided the snorkeling gear and tips on where to look at the reef! Hands down the best trip during Key West! Will definitely book again in the future! Thanks guys!

Michelle WilliamsGoogle

Make Memories To Last A Lifetime

Goodbye, Milton! Hello, perfect sailing weather! ☀️⛵️ We’re back on the water tomorrow (Friday!) after Hurricane Milton passed us by. With the rain gone and the winds just right, it’s the perfect time to sail!

Use code FALLSAIL15 for 15% off your Day Sail or Wind & Wine Sunset Sail. Click the link in our bio to book direct!
Key West taking on those outer bands of #hurricanemilton 🌀 Another Danger Charters Snow day! Hope everyone is staying safe💙⛵️

#hurricane #hurricanemilton #dangercharters #keywest #florida #floridastrong #ocean #storm
Moving the boats for a SECOND time after #helene to a safer spot to ride out the storm. #hurricanemilton is coming in hot stay safe!!!!🌀💙#dangercharterskeywest
Prepping for the second hurricane🌀! #hurricanemilton
Stay safe! Floridas got this!💙🌀 

#dangercharterskeywest #keywest #hurricanehelene #hurricanemilton
Ending a day of kayaking/snorkeling with a sunset🌅 The afternoon sails are always a favorite because you can enjoy sailing, snorkeling, kayaking, and drinks. And after all that, you can watch the sunset after an eventful day.⛵️🐬💙🏝️🌸
Representing!!! Happy October!🎄🎃👻💀⛵️ #dangercharters
Our Locals🐬💙⛵️🏝️#dangercharters 
There’s always a good chance of us seeing dolphins on our trips, and when we do it never gets old🐬 

#hurricanehelene
#ocean #kayak #mangrove #dangercharters #dangercharterskeywest #keywest #keywesttours #keywestkayaking #keywestlife #florida #marinelife #sailingexperiences #ecosystems #sunshinecoast #islandlife

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Man in board shorts does a summersault off a schooner in Key West
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A group of young women pose for a photo while on a sailing charter with Danger Charters in Key West, FL
Book a Day Sail and get up to 25% off a Wind & Wine Sunset Sail!
The discount applies when both sails are booked together. Add a Day Sail to your cart, and you'll be prompted to add the Wind & Wine Sunset Sail at the reduced price. No promo code needed.