Sail Greenport was created in 1997 to reestablish Greenport as a sailing center, drawing sailors and their boats from the New England and Mid-Atlantic area. Becoming affiliated with WoodenBoat Magazine's WoodenBoat Classic Regatta Series, Sail Greenport is proud to host the Greenport Classic Yacht Regatta in September of each year.

Other Wooden Boat Regattas include the Emperor’s Cup in Marblehead Massachusetts; the Eggamogan Reach Cup in Penobscot, Maine; the Opera House Cup in Nantucket, Massachusetts; the Classic Yacht Regatta in Newport, Rhode Island; the Governor’s Cup Regatta in Essex, Connecticut; the Mayor’s Cup in the New York Harbor; and the Race Rock Regatta in Stonington, Connecticut.

The secondary purpose for Sail Greenport is to educate the resident and transient communities about the sport of sailing and it’s historic connection with the Village of Greenport. To this end the group is teaching courses in navigation, seamanship, coastal pilotage and sailing as well as offering seminars in local maritime history.

Greenport is located on the North Fork of Eastern Long Island and is the terminal end for the Long Island Railroad, Sunrise Coach Lines and the Shelter Island Ferry. Because of its deep-water port and accessible channel, the Village of Greenport plays host each summer to various Tall Ships from around the world. Greenport is a wonderful and easily traveled to, destination village for those looking for a bit of fresh sea air, nautical history, good food and great wines. Please visit the Village of Greenport's website for further information.