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Private “Buy-the-Boat” Courses

Offshore Sail and Power Courses can be booked as a private couple or private family sailing school or private power cruise school experience. We call this “Buy-the-Boat!”

Little or No Sailing or Boating Experience?Private Sailing Lessons for Couples and Families

Get started in sailing with a “Buy-the-Boat 3-day basic sailing course OSS 101; or go from novice to cruise-ready in a “Buy-the-Boat” 8-day Fast Track® to Cruising sailing lessons experience. Want to gain big power boat experience? The 6-day “Buy-the-Boat” Fast Track® to Power Cruise power boat course is your family’s ticket to a world boating fun.

Already Know Sailing Basics?

If you everyone in your party has Basic Keelboat Certification on 26′ or larger sailboats, you can all “test-out” of the first two days of the Fast Track® to Cruising course and book a private “Buy-the-Boat” Live Aboard Cruising Course, learning to handle a 40-50′ monohull or catamaran.Private Sailing Lessons for Couples and Families

“Buy-the-Boat” Private Sail or Power Lessons — the Ultimate Learning Experience

Just you and your spouse or significant other, or you and your immediate family benefit from learning together aboard. “Buy-the-Boat” Private Sailing Lessons or “Buy-the-Boat” Private Powerboat Lessons give you double the amount of time, learning to skipper and crew.

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Please note: The only other person on the boat is one of our expert instructors. If the course you choose includes classroom sessions ashore those classrooms sessions are shared with others who may be learning that same week in the same course on other boats. Maximum 5 allowed in the OSS 101 Learn to Sail course, minimum age 7; maximum 6 in next step cruising courses, minimum age 12.

From start to finish, our instructor was prepared, engaging, patient, and encouraging. The resort was lovely, every detail was in place,  My husband and I both worked in education, so we know that knowing the material is great, but being able to TEACH IT, is a true gift. I can’t believe how much I learned in a week! The course is total submersion – you live, and learn it . . . truly the best kind of instruction.

Susan (and Scott) Mitchell – Ocala, FL

High points of my trip: First is the fun I had on the Colgate 26 and the confidence I developed sailing a small boat in strong winds and decent size waves.
Second is the confidence and patience of my cruising instructor and how his attitude for the sea is contagious. Several times we practiced man-overboard to pick up trash that had fallen off someone else’s boat. His combination of being good steward of our oceans and his asking me to put theory to practice are inspiring. Third is the confidence I gained. I’ve been sailing my Catalina 28 and J/24 on a small Indiana lake for the past decade and I wasn’t sure what sailing on the Gulf of Mexico would bring; by the middle of my week at Offshore Sailing School I knew I was up to the task. I am confident sailing and docking the large Jeanneau 439. I’m ready for the next step in my sailing education.
It is not a coincidence that my three standout memories from my OSS experience involve confidence. OSS develops within its students confidence in their instructors, confidence in the boats, and most importantly confidence in their other abilities. Thank you to you and your wonderful team.

Timothy J. Fry – Miamisburg, OH

The Fast Track to Cruising course far exceeded our Private Sailing Lessons for Couples and Familiesexpectations! We had a great time and learned a ton. It was an amazing week. The best money we’ve every spent! Cheyenne is a great instructor. His calm and unflappable demeanor kept me calm and focused on the task at hand. He is very knowledgeable and willing to share that knowledge and experience. He’s also a great host!

Deanna McCollian – Darien, IL

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To speak to one of our knowledgeable sailing advisors, call 888-454-7015, or 239-454-1700, or email