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Casual Sailing

When no one has to serve on Race Committee and there's clean air for everyone

Weekly Portsmouth Sails

We have an active and diverse Portsmouth fleet: from A-Cats to Force Fives, Sunfish, Wetas, and Hobies.


In the summertime we take advantage of the long evenings with Wednesday night sails, and in the winter we wrap up our weeks with a casual Sunday Sail.


We'll throw a few Portsmouth boats on the water, burgers on the grill, and later grab a dark and stormy to watch the sunset on the pier.

Day + Overnight Cruising

Buttonwood Bay is amazing, but there is so much more to see and do sailing around the Florida keys. 

Every so often we get our crews together and assemble our bigger boats and head out beyond Buttonwood Sound: Pumpkin Key to Lignamvitie to Thursday’s Cove, or sometimes up north to Key Biscayne. Just to name a few.

From overnight cruises, joining forces with neighboring clubs, or just meandering around our beautiful island, we always have a great time.

Full Moons, Picnics, etc.

There is always a good excuse to go sailing, and we take advantage of every one we find.


Whether it's an all-comer's sail below a full-moon or a group trip to take a picnic to the wild beach and turquoise waters of Nest Key, 

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