Sailing Sarasota

Sarasota is a sailor's delight. Dolphins leap along side starboard and port, and manatees lumber in our tepid waters; exotic birds nest on mangrove islands and scamper along sandy beaches. Our picturesque gulf, bays and inlets are perfect for dropping anchor, and reveal the secrets of Sarasota’s beauty by sea. There are many ways to explore paradise from this peaceful point of view. From dyed-in-the-wool sailors to babes in the woods, anyone can get on board. 

Batten down the hatches, hoist the sails and take the helm; or sit back, champagne in hand, and see how the mainsail (and sun) sets.

Sarasota Sailing Squadron

Not one, but several sailing clubs here accommodate salty dogs, old or new. If you've got saltwater coursing through the veins, find a special camaraderie at Sarasota Sailing Squadron. The Squadron hosts races, regattas (local and international), cruises, environmental projects, parties and fundraisers. It’s an ideal setting for sailing instruction as well; the Sarasota Sailing Squadron and Sail Sarasota Inc. offer adult lessons and training. As for youth, the Sarasota Youth Sailing Program and for the Ladies the Luffing Ladies all teach sailing from their location near Ken Thompson Park. Veteran sailors Tim and Jan Solomon of Key Sailing describe it as "the place that gave us our passion for sailing back in high school. They are nothing short of amazing."

Sailing in Venice

Farther south, the Venice Sailing Squadron organizes races, cruises and bountiful monthly potluck dinners followed by informative programs related to sailing. It is a sponsor of the annual Crow’s Nest and Shark’s Tooth Regattas and holds around-the-buoy races, distance races and sundown rallies monthly, September through May. The club also plans monthly cruises to various ports of call. Anyone can join, the only prerequisite being an interest in sailing.

The Venice Sail & Power Squadron, a unit of the United States Power Squadrons, is dedicated to boating safety. Regular monthly meetings and classroom instruction affords members the opportunity to further their nautical education to ensure safe sailing as well as power boating.

Sara-bay Sailing School & Charter

Don’t know a halyard from a cunningham? Sara-Bay Sailing School & Charter offers a full range of American Sailing Association (ASA) certified courses. While it also provides captained charters and sailboat rentals for day sailing, its focus is on introducing landlubbers to the rewards of being in control at sea. "We turn people's dream of sailing into a reality,” says Capt. Bill Brooker. He and two other certified instructors have a total of more than a century of sailing experience.

The Basic Keelboat course covers tacking, jibing, points-of-sail, man overboard recovery and more. Basic Coastal Cruising includes docking, anchoring, reefing and other auxiliary skills. Bareboat Chartering prepares students for chartering a boat in the islands, with an overnight cruise down the coast to Boca Grande.

Freedom Boat Club

Once you’ve learned the ropes, or even if you haven’t, consider Freedom Boat Club, where you can “own the water, not the boat.” Members have unlimited use of all boats in the fleets of the club's 59 locations throughout the country. When you arrive your boat is always ready to go; when you return you simply walk away. There is none of the expense, maintenance and concerns that accompany traditional boat ownership.

“Most of our members are powerboaters, but those who want to go back a thousand years and learn what ancient sailors knew can do it here,” explains FBC President Bob Daley. “Part of the package is we teach you to sail. That in itself creates a special bond between our sailing members, the Club and the stars.” FBC is also highly endorsed by the Solomons of Key Sailing, who are lifetime founding members and often avail themselves to teach club members how to sail.

Key Sailing

For the best of both worlds, choose Key Sailing, an award-winning, five-star rated attraction. Capt. Tim Solomon and his wife, Jan, own the Key Breeze, a 1989 41-foot Morgan Classic II Sloop. Their unique philosophy is to limit the number of guests to six, ensuring a comfortable, intimate experience. However, private parties of up to 12 are always welcome. Private charters are affordable, even for two. And all gratuities go to local and global nonprofit organizations.

Tim and Jan learned to sail at the Sarasota Sailing Squadron and have been sailing Sarasota together since 1973. The bayfront veterans' park is named in honor of Jan's father, Chaplain J.D. Hamel, and Jan was named 2009 Siesta Key Chamber of Commerce Business Person of the Year. U.S. Coast Guard Master Capt. Tim is also a licensed ordained minister who performs weddings on board, has a day in the city of Sarasota officially named in his honor and will let guests pose with an authentic key to the city of Sarasota.

As Official Educational Vessel of Sarasota by Sarasota County Proclamation, Key Breeze is host to Sarasota County Vo-Tech Adult Enrichment Programs and also offers annual complimentary field trips to Sarasota County schools. The Key Breeze was a filming site for the 2010 Sarasota Film Festival and has also appeared on national television.

While taking the helm is optional, all Key Sailing guests are treated to Tempur-Pedic cushions, customized music, soft drinks and snacks en route — Jan even makes "Starbucks runs"— personalized photo albums, and, as Jan says, "fresh air, fine chocolates and a few hours of peace on earth."

Whether you are a local or a visitor, a novice or not, when it comes to sailing, there are many fish in the sea. “Ketch” the one that’s right for you, and you’ll never want to abandon ship!