Sailing Lessons

Private Instruction on Your Boat can be Offered Every Weekend From June to September

The more you sail, the more confident you will become in your vessel and your ability to handle it safely in different conditions. Private lessons may be just your answer. You may have recently acquired a new boat and want to accelerate your learning curve on how best to handle it or modify how it is rigged. You might want to improve one specific skill.  You may not need an ASA certification. Most sailors approach docking like getting their teeth drilled. They know one gust of wind at the wrong moment can make the task truly daunting. With coaching we can help you to dock your boat with pride instead of dread. You might want to know how best to trim your sails to really go fast. If you are not in Greenport, we can send an instructor to you at a port along Long Island Sound, or LI's  South Shore,at the best time for you. The instructor will be matched to your needs to ensure you reach your goals. Surprise the sailor you love with a gift certificate for one or more private lessons. He might never think to buy lessons for himself but might find it a unique and special gift for Father's Day or his birthday. Gentlemen, you might like to do the same for a special lady in your life for Mother's Day or a birthday so she can assist more when underway or provide safety backup for you. Fee: $85 per hour with a 3 hour minimum for one or two people on YOUR  boat nearby in Greenport.  Fees by prior arrangement in other locations based on travel time to you. Four hour minimum if we come to you. Please call or email your interest in private instruction. 917-912-6342 or

Special 6 Hour Intro to Sailing Classes for Men and Women

Sail Long Island is offering half day classes (Saturdays 9:00 a.m.-noon) to introduce you to the basics of sailing so you can see if you like it. Perhaps you are considering the purchase of a small boat and want to understand the wind and how to harness it. Originally conceived as a special introductory course for women only, several men have asked us to offer them the same course so they, too, can learn the very basics of sailing. So why should we be sexist about it? Ladies, if you prefer a class with women only, tell us and we will try our best to arrange one if you don't have your own group. As with learning to drive, it is often best to learn from a professional instructor, not a friend or relative. Maybe you envy the folks you see out sailing when you are ashore. It is our end goal to empower you to understand that you can handle a sailboat with aplomb with proper training.. Optimizing mechanical advantage, you can learn to do all the tasks on a larger sailboat needed to safely leave the dock and head out onto the briny. Gals should know boat handling basics even if they plan to just sit in the cockpit, and enjoy the view. What if you are out sailing with friends and something happens to the "Captain" or you need to take the helm immediately in an emergency? What if the person you are sailing with needs to go below and you are the only other crew person on board? Do you know how to use the VHF radio to call for help if something goes wrong? Can you assist in sail trim? Do you understand the basic Navigation rules of the road to avoid a collision?  Would you be able to recover a person or a pet, or something else that may have fallen overboard? My family has recovered practice questions for a math test, boat shoes and hats that have fallen into the drink so Overboard Recovery Drills are more practical than you may think. This program might also appeal to you if you have bought a boat of your own and want to sail it with confidence. These intro classes are a good first step. They will not lead to an ASA certification, but we hope you will enjoy them enough to proceed to the ASA Basic Keelboat course (16 hours of instruction is $595 per person including ASA study materials, test and first year ASA membership). Sailing is much more fun if you know what is going on around you. It's safer, too. $295 for two half days (total 6 hours) of basic instruction. Please call 917-912-6342 or or email

Interested in Learning the Basics of Non-Spinnaker Big Boat Racing?

The Joie de Vivre racing past the competition  The best thing about racing is that it sharpens your skills. We will be racing Joie de Vivre in a few local races during the season starting on June 18th in the Brewers TIME Warp Regatta.; (Photo here is of the tired but happy Whitebread Crew accepting our 2nd place trophy in Whitebread 19 in Columbus Day weekend 2012); In 2010 we won the Brewer End of Season race. Mostly we try to have fun. Call us if you would like an inside look at racing a larger boat around the buoys. The keys to success are wind and water strategy, sail trim, and steering the best course. Most important is to have a great day on the water. Fee is $125 per person for a fun day on the water from June, through September; only $100 per day in October including North Fork hot apple cider to keep you warm in the fall. Please call or email your interest in racing with us. 917-912-6342 or


Star Watching Sails on Moonless Weekends

How about sailing lessons during the day followed by star watching in the evening? If you are into star gazing you know how hard it is to enjoy in New York City or any other urban environment with all the city lights. The moon is also a big impediment to viewing the night sky because of how bright it can be. This year our two star watching opportunities will be combined with our cruise to New England, ports as yet to be determined. Maybe Maine for Advanced Coastal Cruising students or to Martha's Vineyard last week of July and first 10 days of August. Check back for more details  Some dates on the cruise will coincide with days when the bright moon won't be hampering our view of the stars. Armed with a few trusty star charts and some flashlights to show our fellow boat mates what constellations we see, we can enjoy these special opportunities if the weather cooperates and doesn't foil our efforts with a big cloud cover.  Note our annual 4 day holiday trip to Newport over July 4th will include possible stops in Block Island, Stonington CT, Lake Montauk or Fishers island depending on where the wind blows us and crew preferences. 2 day adventure weekends, $595 per person; 3 days, $950; both + provisions. July 4th four day trip to Newport special price of $1095 per person. Discounts for 2 or more people sharing a cabin. Please call for details. 917-912-6342 or email