Joie de Vivre - Our Flagship vessel is a  Pearson 36-2

Welcome to Sail Long Island!

Our American Sailing Association sailing school is located on Long Island's beautiful North Fork at the Brewer Yacht Yard in Greenport, New York. Whether you are a beginning sailor or have years of experience, we are here to help you acquire or improve the skills you need to handle a sailboat safely, knowledgeably, and confidently. Through our American Sailing Association affiliation, we can offer you certification if that is your goal. Our location is in the heart of some of the best sailing destinations on the East Coast of the United States. Think of the America's Cup races in Newport or the excitement of Block Island Race week, both held nearby because of the great winds at the eastern end of Long Island. Sail with us in 2015 to historic whaling ports like Mystic and Fishers Island and Stonington, CT and to sailing meccas like Block Island, Cuttyhunk and Newport, RI. You can also cruise with us in late July  and in August this year to Newport, New London, Buzzards Bay, through the Cape Cod Canal and onto the Massachusetts Coast. Visit the Boston Islands, Salem, Marblehead. Vineyard. Then we'll go continue "Down East" to Maine. We only do this trip about every five years so this is your chance. We'll head to Portland, Rockland and points east. On the way back we'll pass through Buzzard's Bay, probably Woods Hole to Martha's Vineyard, and back to Greenport via Newport.  Pick the days that work for you and join our crew. If you book early you can find reasonable one way fares to Boston, Portland and Rockland for a crew change..

Knowledge is Power (in this case SAIL Power!)

Sailboats are special and the greenest of ways to travel. As you learn how to fill your sails with wind and move swiftly through the water, you will also fill yourself with pride in your growing knowledge. Many of us live in the fast lane. Sailing slows you down in very positive ways. It relaxes and refreshes you. It is as much about "how you get there" as it is about "where you are going." Let us help you learn to harness the wind, understand the water, and to anticipate the weather you are likely to encounter along the way. We will teach you the new skills you need or improve the ones you already have. If our classes are not at convenient times, we offer private instruction.

Learn in Beautiful Surroundings on Eastern Long Island and Join us for big boat racing in the spring and the fall in the waters near Greenport. Come along for the famous all day Whitebread Race around Shelter Island on Columbus Day weekend.

While the days are shorter, Fall sailing has its own special charms.  Its cooler and more comfortable and the winds are better.  It's also when Sail Long Island offers its best opportunity for you to get time on the water for a very reasonable price.  Come sail for the day for just $125 per person for hours and hours on the water.  Captain Joan will provide North Fork Apple Cider and a great time. Big boat races are fun and a great way to learn so be sure to sign up early. And now and then, we win a trophy when we race. Other days we just go out and day sail

Excellent Instructors Who Love to Sail

Our owner, Captain Joan Lappin, first learned to sail in nearby Shinnecock and Peconic Bays. She knows the local waters around Shelter Island and Eastern Long Island Sound like the back of her hand and knows what a great place they are to learn to sail. No wind shadows from skyscrapers. No cruise ships, tug boats, or water taxis to dodge as you learn to come about. Reading books is helpful but like every other sport, practice makes perfect. There is no substitute for time on the water. Our instructors are USCG licensed captains and each has attained ASA certification. They love to sail, have been sailing for decades, and they enjoy sharing what they know with you.