Private Sailing Lessons: Couples Sailing Courses & Romantic sailing getaways

Is your sailing dream to...?

Own or rent a mid-sized sailboat and a couple sailing near home in your free time?
Get into racing and enjoy friendly competition together in local fleets?
Sail a big boat on short or extended cruises together?
Charter in the Caribbean and exotic ports all over the world for a romantic sailing experience?
Try something new and productive on your next getaway?
Enjoy learning together - just the two of you on a private sailing getaway?

You can do all this and more at any Offshore Sailing School campus, in private couples sailing courses. Seasoned sailors call it “short-handed” sailing. Sailors who know the sheer delight of sharing a sailing adventure alone - with a spouse, son, daughter, or best friend – call it sheer bliss.

Our sailing for two lessons are designed for couples, friends, parents and siblings that plan someday to sail or cruise together with no one else aboard, or just want a unique and rewarding time away without others around. When you take one of our private sailing lessons vacations, the inspiring gift of trust and confidence in one another is realized. In less than a week you will have found a new and wonderful lifetime pursuit and developed respect for each other’s abilities to handle a Colgate 26 or large cruising boat with ease.

“My wife and I had not sailed for over 20 years. The course was a 25th anniversary gift. You have made me a hero!”
Chris Walker - Ipswich, MA

Private Learn to Sail Lessons

You’ll stay at a fabulous destination resort in Florida, the Chesapeake or the British Virgin Islands while enjoying private sailing lessons, learning to sail the award-winning Colgate 26 – training boat of choice for the U.S. Naval and Coast Guard Academies. You may also take these couples sailing courses at our New Jersey and New York locations on weekdays and weekends.

With our Private Sailing Vacations, each day is a new adventure as you take the helm and work as a team, learning to sail this state-of-the-art performance daysailer with your expert Offshore Sailing School instructor. At course end you’ll sail together on your test sail without the instructor aboard – a super bonus and start of a lifetime of happy days as a couple sailing together on the water.

Private Performance Sailing Lessons

When you have mastered the basics, you may want to learn more about go-fast sailing and round-the-buoy racing couples sailing lessons. Performance Sailing is also taught on the sprightly Colgate 26, which is used for International Team Racing competition each summer. You may take this course on a three-day or week-long schedule at two Florida resort locations, on the Chesapeake and in New York City and New Jersey. If you live in the New York Metro region you can join our New York and New Jersey Sailing Club on the Hudson River after you finish and have a ball racing with other club members all season long.

Private Fast Track to Cruising Lessons

Private Sailing Vacations Combine your Private Sailing Lessons from your Learn to Sail adventure with a cruising course and go from no experience to ready-to-cruise in just one week. This is Fast Track to Cruising® - the fastest and easiest way to get ready for big boat sailing.

You’ll start with two days on a Colgate 26, then segue to a 42’ to 51’ cruising boat, either staying ashore the entire time or living aboard for the duration of the cruising course. Depending on the location you choose, you’ll sail on the perfect catamaran or monohull for charter from The Moorings, or the latest live-aboard cruising design from Hunter Marine or other manufacturers chosen by Offshore Sailing School for their performance, living space and comfort aboard. At course end you’ll marvel at all you have learned and enjoy deep respect for each other’s skills and command aboard. Best of all, you can look forward to many years ahead of living the sailing life with endless sailing opportunities to share.

If you have good sailing experience on mid-sized daysailers, you can go direct to one of our cruising courses described at the links below. You’ll need Colgate Day Sailing Certification or US SAILING Basic Keelboat Certification but you may “challenge” these tests for a nominal fee during the course.

“Our experience with OSS was one of our most memorable, challenging and life-changing experiences. We tackled the private live-aboard to see if the two of us could handle a boat of that size and to see if it might be a lifestyle we could enjoy. We did, and it is. Within one week, we gained confidence in our skills. We went home and put our house up for sale. Mere words cannot describe the emotions we developed for the love and respect of the sea . . . and each other.”
Larry and Mimi Amerson – Springfield, GA

THE FAST TRACK TO CRUISING COURSE FOR TWO

THE LEARN TO SAIL COURSE FOR TWO

THE PERFORMANCE SAILING COURSE FOR TWO

THE BAREBOAT CRUISING PREPARATION COURSE FOR TWO

THE LIVE ABOARD CRUISING COURSE FOR TWO

to get a quote on Sailing for Two and the couples sailing courses of your choice today!