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Private Courses

Boating and sailing have become very popular ways to get away during stressful times. Across the country, sailboat sales and powerboat sales are at an all-time high. There is something truly special about being out on the water, mastering the sailing skills to confidently handle a big cruising yacht, in the open air, propelled by wind alone.

Learn Big Boat Sailing Skills in a Private Setting

Now you can do just that with confidence, in a private setting with a dedicated, professional sailing instructor whose time is solely yours throughout this unique sailing lessons opportunity. Our Buy-the-Boat Private Cruising Lessons option allows you and a loved one or friend, or your family, to reserve a cruising sailboat and Offshore Sailing School instructor just for yourselves. You get double the amount of learning time on the helm and as crew. Request a Quote today.

From Couch to the Captain’s Chair in One Week

These Buy-the-Boat Private Fast Track® Cruising Lessons take you from the “couch to the captain’s chair” at special pricing. Fast Track® to Cruising is our most popular sailing lessons program where normally the class group is up to four who may or may not know each other. In this private Buy-the-Boat sailing lessons setting, you’ll 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.

First You Learn Sailing Basics, Then Step Aboard an Amazing Cruising Yacht 

In your Fast Track to Cruising® Course, your first two days are spent 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 quickly. Then you board a 40′-50′ cruising yacht, sailing or power catamaran with plenty of space for you and your instructor.

In our Fast Track® to Powerboat Cruising Course, you live, learn and eat aboard the power catamaran from Monday to Saturday, except two dinners ashore.

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 forever! There is just one cruising boat at each of the locations below, so first come first served to purchase a Buy-the-Boat package. There are also 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
  • Textbooks sent in advance to study
  • Three US Sailing Certifications for Fast Track to Cruising – Basic Keelboat, Basic Cruising and Bareboat Cruising
  • Two US Sailing Certifications for Live Aboard Cruising only – Basic Cruising and Bareboat Cruising
  • US Sailing Catamaran Endorsement Certificate if you learn aboard a catamaran
  • Course certificate and logbook
  • Accommodations at a partner resort – 3 nights for Fast Track® courses, 1 night for Live Aboard Courses
  • Resort fees and taxes where applicable
  • All breakfasts, lunches and three dinners aboard yacht from Monday lunch through Saturday breakfast

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