Sunset Sail Key West

Sunset Sail Key West Sunset Sail Key West sails a fleet of historic and beautifully restored classic yachts. Set sail for one of our daily public and private sailing trips!
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Sunset Sail Key West -
Where we sail “For the Love of Sailing”
Browse and book your sail online! There's no better way to experience the Florida Keys than right on the water, and there's no better charter to trust with your tour than Sunset Sail Key West. With years of experience and a lifetime of passion, our fleet of locally owned sailboats and personable sailors will show you all the beauty t

hat Key West has to offer. As you join us for a sunset, starlight, or snorkel sail, you'll find that the sparkling waters of the Florida Keys have a way of bringing people together. Our dedicated team is flexible, accommodating, and dedicated to making your sailing experience as smooth and personalized as possible.

We’ve got some last minute availability for tonight’s private charter sunset sail and cut $100 off the price. It’s too n...
01/19/2025

We’ve got some last minute availability for tonight’s private charter sunset sail and cut $100 off the price. It’s too nice not to! Booking link in comments.

When you are looking for something extra special and unlike the rest, give us a call and book your truly classic sail on...
01/19/2025

When you are looking for something extra special and unlike the rest, give us a call and book your truly classic sail onboard our storied yachts!

Timeless elegance! Throwback to last years photo shoot with Nautica onboard the When And If! Join us for a sail and cap...
01/17/2025

Timeless elegance! Throwback to last years photo shoot with Nautica onboard the When And If! Join us for a sail and capture your pictures!

01/13/2025

Join us aboard General Patton’s 1939 Schooner yacht and become part of her story to fulfill General Patton’s dream of “When the war is over and If I return, Beatrice and I will sail around the World!”

Meet our fleet! 1939 Schooner When And If: built for then Colonel George S. Patton and christened from Patton’s famous q...
01/12/2025

Meet our fleet!
1939 Schooner When And If: built for then Colonel George S. Patton and christened from Patton’s famous quote “ When the war is over and if I return Beatrice and I will sail around the World” exceptionally maintained and open to the public while raising funds to fulfill the ship’s destiny to sail round the World

1930 Schooner Malabar X (10): Famed yacht designers personal yacht and the culmination of years of practice, Malabar X was the last and largest schooner that Alden had built for his award winning Malabar series. Malabar X won 1st in class in the 1930 Bermuda race and then again in 1932 she won 1st overall, including a victory over the lightning fast S/Y Dorade! Completely rebuilt in 2002 and delivered to Barcelona in 2008 where she stayed until we acquired her and returned her to the I.S flag and gained USCG certification to carry 32 guests.

Sloop High Tide: Conch Republic Navy’s official “Sloop of Peace” High Tide is a 1978 Glander built in Islamorada, FL as Key West’s first USCG certified sailing vessel. Completely rebuilt in 2013, High Tide is Coast Guard certified for up to 12 guests and offers exclusive and personalized private charters while providing our crew a platform to learn and hone their skills as sailors while sharing our love of Key West with our guests.

Join us for a truly unique and unmatched sailing experience in Key West!

We love sharing our special piece of paradise with our guests and followers! Where is your paradise?
01/06/2025

We love sharing our special piece of paradise with our guests and followers! Where is your paradise?

01/05/2025

Set sail for the breathtaking views aboard one of our classic and truly historic sailing yachts!

What an evening for a sail! Thank you Capt. Jonathan King for capturing such a cool shot!
01/03/2025

What an evening for a sail! Thank you Capt. Jonathan King for capturing such a cool shot!



01/01/2025

Start the New Year off right with a private charter sunset sail! We haven’t had availability for this in 3 weeks. Must be a glitch in the matrix… Today and tomorrow’s are available, link in comments

Sunset Sail Key West sails a fleet of historic and beautifully restored classic yachts. Set sail for one of our daily public and private sailing trips!
Sunset Sail Key West -
Where we sail “For the Love of Sailing”
Browse and book your sail online!

Happy New Year from all of us @ Sunset Sail Key West! May 2025 be filled with peace and adventures under sail! Thank you...
12/31/2024

Happy New Year from all of us @ Sunset Sail Key West! May 2025 be filled with peace and adventures under sail! Thank you to all of our guests for making 2024 a success!

12/29/2024

Sailing into the new year in style! Hop aboard, we’d love to have you!!

12/24/2024

Happy Holidays! And Happy Sailing!

Moody vibes for the winter solstice sunset tonight ❄️ 🌅 ❄️
12/21/2024

Moody vibes for the winter solstice sunset tonight ❄️ 🌅 ❄️

Yes! Yes! Yes!!!!Thank you for choosing us to sail you into your next chapter! Congratulations!
12/20/2024

Yes! Yes! Yes!!!!
Thank you for choosing us to sail you into your next chapter!
Congratulations!

Congratulations!! She said YES!! @ When And If
12/14/2024

Congratulations!! She said YES!! @ When And If

12/10/2024

Step aboard and sail away with us! Sail When And If

Small Business Saturday makes a lot more cents for the local community than Black Friday on Amazon or the likes. Book yo...
11/30/2024

Small Business Saturday makes a lot more cents for the local community than Black Friday on Amazon or the likes.
Book your charter today!

Address

202 William Street
Key West, FL
33040

Opening Hours

Monday 8am - 10pm
Tuesday 8am - 10pm
Wednesday 8am - 10pm
Thursday 8am - 10pm
Friday 8am - 10pm
Saturday 8am - 10pm
Sunday 8am - 10pm

Telephone

+13055874488

Website

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Videos

Join us aboard General Patton’s 1939 Schooner yacht and become part of her story to fulfill General Patton’s dream of “When the war is over and If I return, Beatrice and I will sail around the World!”

We still sail all over the place for all sorts of reasons but Key West is finally our official home port for our historic schooner When And If

Set sail for the breathtaking views aboard one of our classic and truly historic sailing yachts! #sunset #keywest #Trulyhistoric #Schooner #keywestsunset #sunsetsailkeywest #keywestsbestsecrets #hiddengem #keywestwedding #keywestflorida

Key West Sailing is Simply the Best!
Key West Sailing is Simply the Best!

Sailing into the new year in style! Hop aboard, we’d love to have you!!

Sunset Sail Key West
Sunset Sail Key West

Step aboard and sail away with us! Sail When And If

With the wind in the sails and wine in your hand, a classic schooner sunset sail does not disappoint! #keywest #sunsetsailkeywest #keywestsbestsecrets

You don’t want to miss this!! Join us for a memorable and one of a kind experience!

The relaunching of John Alden’s magnum opus - Malabar X (ten) was a highlight of our last month and Wednesday we are planning on re stepping the masts! Step by step, we are bringing this historic ship and all her stories back to life for all to share. All we ask is that you think of us and our fleet of storied classic yachts when you are planning your visit to Key West. It is all thanks to you that we are able to keep history sailing for all to experience!

Welcome back to the USA Malabar X (ten)!!

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