Enjoy a tour on one of Key West’s best attractions, the schooner Summer Wind. We sail from Stock Island Marina Village, a short drive or taxi ride from Old Key West. See the islands from the best vantage point around, the deck of a schooner! But unlike the larger schooners of Key West, we only take six passengers at a time, so you always have plenty of room to spread out and enjoy your own private space. We pride ourselves on our unique combination of intimacy and privacy that no other schooner in Key West can match.

With two hour tours both day and night and private charters customized to meet your every desire, we’re sure to make wonderful memories for you and your special someone. Wherever we sail, we’re known as the most romantic thing to do in that port. Why should Key West be any different? All of our trips are BYOB, so bring along your favorite bottle of wine and we’ll treat you to a special day on the Summer Wind.

We’re all lifelong sailors who just can’t get enough of the sea and the salt air, and we love to share our enthusiasm for sailing with everyone we meet.Learn More
The Summer Wind is a steel-hulled, Junk-rigged ocean cruising schooner designed by noted naval architect Thomas E. Colvin.Learn More
Listen to all the music we play on the schooner Summer Wind all the time on our own ShoutCast Internet radio station, SummerWindRadio.com!Learn More

About Our Public Sails

Have fun sailing in paradise!

All of our public sails are 2 hours. We start the day helping you recover from the night before with our exclusive Morning Hangover Cure Cruise. Fresh squeezed orange juice, Cuban coffee and a visit from the Hangover Hospital staff right at the boat! The Afternoon Cruise is full of Florida sunshine and lots of original Key West music featured on our own internet radio station, Summer Wind Radio. The nights in Key West start off with an old tradition, the Sunset Sail. We’ll give you a fantastic view of the sunset from the water. And if that’s not enough, our Stars On The Water Sail is the perfect way to sail in the moonlight. The Summer Wind is limited to 6 passengers, so it’s always comfortable and intimate. And you don’t have to rent the whole boat – we sell individual tickets. So join us for one of the best memories in Cayo Hueso! We’re also available for private charter. Just ask for more information.

What Others Are Saying

“I’m a history teacher and I loved your History Sail. I learned some new things I’ll use in my classroom. Thanks for a great trip!”
Hank, History Sail
“We were treated like family and loved every minute of the exciting ride.”
Jim, Tropical Sail
“My friends and I had a great time on your boat. It’s a real treat!”
Terry, Tropical Sail
“We loved the History Sail! Had a beautiful morning on the water and learned quite a few things.”
Lynn, History Sail
“Very beautiful and relaxing.”
Angie, Sunset Sail
“This is the best kept secret. Everyone should do this!”
Pat, Moonlight Sail
“Seriously… as good as it gets!!!”
Teresa, Sunset Sail
“This really is one of the most romantic things you can do! I really recommend it!”
Maggie, Sunset Sail