You'll Just Love Where we Sail

Print this chart of our fabulous cruising waters to select your weekend destination with Sail Long Island. We have so many choices, we can go where the wind blows us. Combine learning to sail with a fabulous destination you have always wanted to visit.

And Yes! You've Found the Best Place to Learn to Cruise

Just look at our vast choices for adventure sailing to a terrific destination port. Join us this summer for a special three or four day expedition to Block Island or Newport RI. If you only have 2 days, perhaps one of our star gazing weekends will appeal to you. No matter how many days you spend onboard, our primary goal is for you to master your sailing skills. To learn about cruising, we think you should learn to provision the boat, participate in anchoring, eat some meals prepared in the galley, sleep aboard and really experience the cruising life. Have morning coffee on deck as we plan our day's sail. On destination cruises we will plot a course and monitor how well we are following it. We will work on sail trim, boat handling, piloting and navigation,rules of the road and knots. Ah, so much to learn and so little time. There is no substitute for "sea time" and and this is the perfect way to get it.

Check our schedule then pick your favorite adventure port of call: Mystic, Block Island, Cuttyhunk, Block Island, Watch Hill, Fishers Island, Stonington, Essex, Newport, Sag Harbor, Montauk, or 3 Mile Harbor. We'll visit all of them this summer. Learn to sail en route to one of these romantic places you've only read about. All can be reached in a single day from Greenport. Shown here are photos of just a few of these great destinations. Call to book now while space is still available for your favorite destination at 917-912-6342.

Mystic Seaport Museum, CT

Up the Mystic River in CT. is Mystic Seaport, a maritime treasure. With interesting exhibits, planetarium shows, and special events, this is a very special treat as part of a longer sail. The trip up river is one in which you must mind the channel markers and pass through two bridges which open for mariners. Once we arrive, we become part of the museum itself while tied up at the dock. Landlubber visitors willl admire the Joie de Vivre as they walk by. At night, when we are still tied up in the boat basin after the museum closes, you will be transported back a century to the time when whaling and coastal ships were built in the Mystic River. You'll love the photographic opportunities here at sunrise or at sunset so be sure to bring your camera along.

Cuttyhunk, MA

Cuttyhunk is 12 miles south of New Bedford MA and is the western-most of the Elizabethan Islands which lie between the coast of Cape Cod and Martha's Vineyard, left behind by the retreat of the last glacier 10,000 years ago. The description of Cuttyhunk on its own website is as follows: "Cuttyhunk Island is a place to do a whole lot of nothing. Cuttyhunk Island has a small beach (which seems to have sand that moves about every year!), a great harbor, good fishing, a few dozen houses, some great ice cream(!), and some beautiful hiking trails. Cuttyhunk does not have discos, bars, malls, a singles scene, a party life, video games, parking lots, traffic, or much action. What Cuttyhunk does have is a quiet, isolated, beautiful, ocean environment, perfect for getting in touch with yourself and your family, or just catching up with your reading! Cuttyhunk is famous for fishing and relaxing." Cuttyhunk derives from the Indian name Poocutohhunkunnoh. Bartholomew Gosnold landed there in 1602. The famous Cuttyhunk Raw Bar Boat delivers freshly dug shellfish right to our cockpit in the harbor.

Newport, RI - The Sailing Capital of the East Coast

There's a lot to do in Newport, the yachting capital of the East Coast. The America's Cup Competition was held here for decades. Visit the Museum of Yachting and IYRS (the International Yacht Restoration School). Tour the famous mansions of the Vanderbilts and Whitneys and a host of other industrial titans of the 1800's. Enjoy a walk along Thames Street and enjoy the shops. Or take a walking tour of historic Newport. Many buildings date back to the 1600's. Religious Toleration made its way into our Constitution because of the founders of Rhode Island including Anne Hutchinson (as in Hutchinson River Parkway) and Roger Williams. Visit the Tuoro Synagogue, the oldest synagogue in the United States where you can see the proclamation of tolerance signed by George Washington. Visit the Redwood Atheneum, the oldest private library in the U.S. or the Newport Historical Society. You have the opportunity to visit Newport with us this summer en route either to or from Maine in late July and mid-August.

Block Island, RI

While you can reach Block Island via ferry from Montauk or New London, it is most thrilling to arrive via sailboat. The New Harbor is in Great Salt Pond which was washed open in the great hurricane of 1938. Learn why sailors flock here for Block Island Race Week year after year. Take an hour island tour by taxicab and you will learn that the center of Block Island is actually below sea level. Walk, bike or rent a moped. Enjoy the beautiful beaches. Eat a local lobster. This windswept island has undergone quite a revival in recent years as a wedding and even a winter destination for a romantic weekend near NYC. You will be transported to another time and place. Come see why. We'll be heading here once or twice in 2010. Call for details.