A wooden footbridge leading to the beach

Our Blog

Sailing Sarasota’s Seas And More

If you have your own sailboat while here in the Longboat Key and Sarasota area, lucky you. If not, no problem. There are schools, charters, cruises and many other means to gliding across the water available. Sailing in Sarasota is more than just fun, it’s a learning experience. The area’s rich ecosystem is teeming with life, whether you’re navigating through the bay or setting out on the open sea, a.k.a the Gulf.

If you’re a novice, this is the perfect place to learn. If you’re an expert mariner, you’ll be in good company. There’s a vibrant culture built around boating here, with over a dozen marinas and several yacht clubs, not to mention regattas and races. One of the best places to start is the Sarasota Sailing Squadron, where young and old can learn to sail. This historic hub for all-things sailing offers instruction, rentals, dockage, social activities, volunteer opportunities and much more. Similarly, Sara-Bay Sailing School & Charter, an ASA affiliate, offers personalized instruction as well as charters and rentals.

If you love the idea of a sailboat but don’t necessarily want to captain one, spring for a charter. Key Sailing will help you achieve that wind-in-your-hair, salt-on-your-skin feeling in no time. Captained by a U.S. Coast Guard Master, this yacht takes groups no larger than six from Marina Jack out to sea on day or sunset sails. For a different kind of sailing experience, Kathleen D Sailing Catamarans does daily public excursions as well as private charters. Choose from Dolphin Watch, Sunset Sail, True Sail or Longboat Pass Adventure, which includes sailing, snorkeling and kayaking and leaves from Longboat Key.

Once you’ve sailed to your heart’s content, explore some of the other ways to enjoy the water here. Siesta Key Watersports is a one-stop shop for visitors looking to try out parasailing (the highest in the area) or a three-seater jet ski. And while there’s nothing like a sailboat coasting over the surf, sail flapping in the wind, renting a hurricane deck boat is a definite blast. Luckily, there’s no reason not to do both during your stay here.