Adventure Sailing

You'll Just Love Where we Sail

Our Fabulous Sailing Waters

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 avariety of terrific destination ports. 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 and improve 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, Newport,  Block Island, Watch Hill, Fishers Island, Stonington, Essex,  Lake 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. Email us at CaptJoan@SailLongIslanCall to book now while space is still available for your favorite destination at 917-912-6342.

Mystic Seaport Museum, CT

Mystic, CTUp 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.

Newport, Marblehead, Salem,Martha's Vineyard and other stops along the way in 2015

Cuttyhunk Raw Bar In 2015 we'll be cruising  from Greenport on Saturday July 25th returning to the North Fork by Wednesday August 12th.  We'll leave Greenport and head East to Rhode Island for a  night  or two in fabulous Newport.  Then on to the famous Back Eddy restaurant for dinner in Westport MA. We'll head across Buzzards Bay to Onset to be ready to transit the Cape Cod Canal en route to Scituate MA. Then we'll continue on with other boats to the Boston Islands, Marblehead, Salem and back to Boston for a crew change.  Then back through the Canal and Buzzard's Bay for a night in Hadley Harbor the finest gunkhole on the East Coast of the United States to swim and bird watch., We'll head through Wood's Hole and head across Vineyard Sound to Martha's VIneyard for two nights. Like Boston, it's a good place to fly in or out on Jet Blue. From there we'll return to Newport on our way back to Greenport. Check our schedule for the planned dates in each place.  Time of arrival in all locations are subject to weather considerations that may impede our progress. ASA instruction along the way for those who want to do both things at one time. Costs will be based on how many days you spend aboard and whether you want ASA instruction and certification so be sure to call for details after you have checked your own calendar. This is a very special trip for intermediate and advanced sailors that is sure to fill up fast. Some dates have already been spoken for.  Call Capt. Joan for complete information. 917 912 6342 or email her at

Newport, RI - The Sailing Capital of the East Coast

Newport, RIThere'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 Touro 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. We will be in Newport over July 4th weekend, and again from July 25-27.  

Block Island, RI

Block Island, RIWhile 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 in June 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.