Sailing Cruises

We offer 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.


Charleston Harbor Sailing Cruises

Does the thought of a lazy day, lounging on a boat, smelling the ocean air, and being caressed by a comforting breeze blowing through your hair while watching the dolphins jump and play 'til the sun sets sound relaxing?

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

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!

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!

Take an Intro To Sailing Class
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!

Join us for a Sunset Cruise or a Wedding Event 
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...