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Call: (888) 454-7015

Private Courses

In our “private courses” a couple or family learn skills to manage a medium sized day sailor (OSS 101) and larger cruising boats (OSS 103/104/114) in a private environment on the water. The only other person aboard is one of our expert instructors. However, if the course you choose includes classroom sessions ashore (a small but important element) please understand that those classrooms sessions are shared with others who may be learning that same week.

Learn Big Boat Sailing Skills Together 

Buy-the-Boat Private Cruising Lessons are for couples and families who wish to reserve a cruising sailboat or powerboat and Offshore Sailing School instructor for private instruction. You get double the amount of learning time on the helm and as crew while learning aboard. As stated earlier, on-shore classroom sessions, if part of the course you choose, are not private.  Request a Quote today.

Couch to the Captain’s Chair in One Week

Buy-the-Boat Private Fast Track® Cruising Lessons take you from the “couch to the captain’s chair” at buy-the-boat pricing. Fast Track® to Cruising is our most popular sailing lessons program where normally those learning aboard may or may not know each other. In a private Buy-the-Boat course, while aboard (not in the classroom where others may be present) you share an experiential getaway that surrounds you with newly-gained confidence in the great outdoors, while dolphins play in your wake and ospreys fly overhead.

Choose a Sail or Power Private Cruising Course

In the Fast Track to Cruising® Sailing Course, your first two days and three nights are spent ashore while learning the basics of sailing on a lively, open cockpit Colgate 26 – specially designed by our founder Steve Colgate to allow you to advance quickly to larger sailboats. Your on-water lessons are private; the classroom sessions each morning are not private. Then you  board a 40′-50′ monohull or catamaran cruising yacht, with plenty of space for you and your instructor, enjoying six days of private sail or power education.

For those who want to learn on powerboats, the Fast Track® to Powerboat Cruising Course is a 6-day experience on a 37′ to 50′ power cat (short for catamaran) where you board the boat Sunday evening and live, learn and dine aboard (except two dinners ashore) with your private instructor, Monday to Saturday.

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

If You Already Have Basic Sailing Experience . . .

If you already have US Sailing Basic Keelboat Certification and are competent sailing boats up to 25’, or have equivalent experience, you can choose just the Private Buy-the-Boat Live Aboard Course.

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

So What Are You Waiting For?

Bring a friend, a loved one, or your family. Sign up today for the time of your life – in a private learning experience guaranteed to give you the confidence to enjoy sailing or boating forever! Choose your private on-water learning experience now in SW Florida or the British Virgin Islands!  Private flight options to RSW airport in Fort Myers, Florida, or EIS airport on Beef Island/Tortola in the British Virgin Islands for your consideration. We’re happy to provide a list.

Receive peace-of-mind and everything we’ve always included:

  • Your complete course and applicable US Sailing or US Powerboat Certifications
  • Textbooks sent in advance to study
  • Course certificate and logbook
  • Accommodations at the resort where the course is located – 3 nights for Fast Track® sailing courses, 1 night for Live Aboard Sailing Courses
  • Resort fees and taxes where applicable
  • All breakfasts, lunches and three dinners aboard the yacht

The Fast Track to Cruising course far exceeded our expectations! 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

Choose a Location and Sign Up Today

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