Imagine smelling the ocean air, with a comforting breeze blowing through your hair, watching the dolphins jump and play while sailing ’til the sun sets the day. Now THAT sounds relaxing!

With Ocean Sailing Academy's customizable cruises, you can let your imagination sail free, and experience the sailing cruise of your dreams!

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We offer private and semi-private sailing cruises on a variety of vessels!

Booking a private cruise means the route, start time, cruise duration, and vessel are up to you! Half day (3 hours) and full day (6 hours) charters include bottle water and koozies for up to 6 people.

Semi-private cruises are a great way to meet others who share your interest in sailing! Semi-private cruises are pre-assigned a vessel, have pre-determined routes and set times. Rates for semi-private cruises are per passenger and include bottled water.

Contact us for more info, or click book now to browse immediate options.

Charleston Sailing Cruises, Ocean Sailing Academy
Charleston Harbor Sailing, Ocean Sailing Academy

Customize Your Cruise!
Below are a few suggestions as to how you can customize and personalize your sailing cruise:

  • Make it a package and receive a hat/visor, koozie, and an OSA T-Shirt
  • Order a boxed lunch or cater from your favorite restaurant
  • Anchor out and swim at the destination of your choice
  • Head to the blue waters for an adventurous sailing cruise
  • Share your sailing dreams with OSA! If you can dream it, we can do it!

Intro To Sailing
Our Intro to Sail is a fun, adventurous, educational boat ride. You will have the opportunity to steer, handle sails and absorb knowledge from one of our awesome sailing instructors! No experience required!

Sunset Cruises
Sit back with your favorite food and beverages as the sunset falls, outlining Charleston’s stately mansions and church steeples. We hope you have a camera, because you’re going to want one for this cruise! Read More...

What To Bring
Below are a few suggestions of what you might like to bring for your sailing cruise:

  • Sunscreen or sun protection
  • Sunglasses and hat
  • Wind breaker or jacket (weather dependent)
  • Camera
  • Closed-toed, non-marking shoes (no flip flops, please)
  • Soft drink, water, or other beverages (alcohol is permitted, NO GLASS bottles)
  • Share your sailing dreams with OSA! If you can dream it, we can do it!
South Carolina sunset taken portside from a Beneteau by Ocean Sailing Academy