Learn to Sail with Sarasota Sailing Squadron

The Sarasota Sailing Squadron (SSS) is a sailing club located right here in Sarasota on City Island near Ken Thompson Park.  It offers a variety of sailing-related activities and services to its members and the community.  The club is known for its vibrant community, diverse fleet of sailboats, and active racing calendar.  It offers affordable access to the beautiful Sarasota Bay.

History of the Sailing Squadron

The Sarasota Sailing Squadron has a rich history dating back to the late 1930s when a group of teenage buddies formed their own “down to earth” sailing club on the City Pier (where Marina Jacks is located today).  The club ceased during the years of World War II and reformed when the sailors and veterans returned home in 1946, naming it the Sarasota Sailing Squadron.  Their goal was to promote the sport of sailing and make it accessible to the local community.

The initial meetings and activities took place on a small, sandy spit of land near the Ringling Causeway.  The members built makeshift facilities to support their sailing activities.  Over the years, the club grew in membership and facilities.  The early 1950s saw the construction of a clubhouse, which became a central hub for social and sailing events.  The club was officially incorporated as a non-profit organization in 1958.  This formalization helped in organizing events, securing funds, and expanding the club's reach.  From its inception, the Sarasota Sailing Squadron has been deeply embedded in the local community.  It has hosted numerous regattas, races, and social events, drawing sailors from around the region and beyond.

Over the decades, the club's facilities have expanded significantly.  The addition of new docks, boat storage areas, and upgraded clubhouse amenities have made it a premier sailing destination in Florida.  Today, the Sarasota Sailing Squadron continues to be a vibrant and active sailing club.  It hosts local, regional, and national regattas, supports a thriving youth program, and serves as a social hub for sailors and the local community.

What They Sail

The Sarasota Sailing Squadron (SSS) supports a wide variety of sailing vessels, catering to both recreational and competitive sailors.  Some of the boats include:

Dinghies: These small, lightweight boats are popular for both racing and training.  Common classes of dinghies include the Optimist, the Laser, 420 and Sunfish.

Keelboats: These are larger boats with a fixed keel that provide stability and are used for both racing and cruising. Some popular keelboat classes at SSS include J/24, the Sonar and Flying Scot.

Multihulls: These boats have more than one hull, offering speed and stability.  The most popular ones are the Hobie Cats.

Cruising Boats: These larger sailboats are designed for longer voyages and comfortable cruising.  Less common than racing boats, they are part of the Squadron's diverse fleet.

One-Design Classes: The Sarasota Sailing Squadron often hosts races for specific one-design classes, where all boats are identical or similar, ensuring that races are determined by skill rather than equipment advantages.

Custom & Unique Vessels: Members sometimes sail custom or less common boats, reflecting the diverse interests and skills of the sailing community at SSS.

In addition to these boats, the club supports a variety of racing formats, including fleet racing, match racing, and regattas, accommodating different skill levels and sailing interests.

Sailing Lessons for All Ages

It’s never too late to learn to sail and the Sarasota Sailing Squadron offers lessons to members and non-members alike.  The club has a long-standing commitment to youth sailing, offering programs to teach young sailors the basics and advanced techniques of the sport.  These programs have produced many skilled sailors who have gone on to compete at high levels.

So whether you are young or young at heart, there’s no excuse to experience the excitement and fun of sailing!

Participate in a Regatta

A regatta is a series of boat races.  Generally speaking, a regatta will sail 2-3 races with its a fleet and then switch to 2-3 races with its B fleet.  The Sarasota Sailing Squadron hosts numerous annual invitational regattas each year, including a Labor Day Regatta and a Sarasota Bay Multi-Hull Regatta as well as many regattas for its members.

For more information about the Sarasota Sailing Squadron, please visit their website.

After a day on the open water, it doesn’t make sense to go home to a crowded hotel.  Sailing is about freedom and your accommodations should reflect that.  At the Inn on Siesta Key, you can experience vintage Florida and its coastal charm.  Here, life is more secluded, relaxing, and quiet; just like a day of sailing on the waters of beautiful Sarasota Bay.

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