Sailing in Rye

Select Local Merchants

The ASA-certified instructors of New York Sailing School have been teaching the exhilarating art since 1968. With access to a fleet of beginner-friendly Sonar 23 skiffs, they instruct courses both on land and water, venturing out into the Long Island Sound with tender-footed aquanauts and Waterworld fanboys alike. NYSS alumni and ASA-certified sailors are also welcome to rent boats for daytime jaunts across the water.

22 Pelham Rd
New Rochelle,
NY
US

Since 2004, the first-aid- and CPR-trained crew at Port Sailing School has ferried passengers over Manhasset Bay for sailing lessons, charters, camps, and certification courses aboard the school's fleet. The outfit's nine noble vessels include such seafaring specimens as the J 24 keelboat, the two-cabin Beneteau 36, and the Sonar 23, designated as the fleet’s primary lesson boat for its roomy cockpit and no-mutinies record. Aboard the Sonar 23, students learn sailing skills and marine laws through instructional courses that range from private introductory sailing lessons to state safety certifications. Based on the course topic, lessons may focus on such boating aspects as docking, mooring pickup, anchoring, or advanced racing techniques, each dictated by the desires of the student and the daily attitude of the sea.

86 Orchard Beach Blvd.
Port Washington,
NY
US

Atlantic Outfitters facilitates maritime excursions with its stable of paddle-propelled vessels. From the fiberglass-ensconced safety of two sleek kayaks, or from the commanding view afforded by two standup paddleboards, seafaring friends can spend two hours exploring the watery expanses, tributaries, and wooded shorelines of the pristine Manhasset Bay. During the journey, paddlers can picnic on the open water, use their feet as anchors in the shallows along sandy beaches, or reenact favorite scenes from a documentary about waterfowl. Numerous kayak launch sites along the coast provide easy access to the bay.

405 Main St
Port Washington,
NY
US

The future of Oyster Bay is in good hands with The WaterFront Center, a nonprofit U.S. Sailing–accredited facility that teaches both youths and adults to conserve their local environment. In addition to demonstrating the importance of environmental responsibility, the center also instills sailing skills in people of all ages, from their Lil’ Luffers class for third and fourth graders to US Sailing certification for those ready to take the boat out on their own. For corporate groups, they teach a different kind of lesson out on the water with outings designed to teach team development or effective communication. The WaterFront Center also rents sailboats and kayaks to veteran boaters or trustworthy gusts of wind.

1 West End Avenue
Oyster Bay,
NY
US

A new graduate of Martin van Breems' Basic Keelboat course out on his first sail was pounded by driving rain and battered by winds raging at almost 35 miles per hour, but he kept his cool. When his fellow sailors found him, his jib was rolled, his main was reefed, and Breems recalls that it, "felt pretty darn good to see him doing exactly what he should have done in difficult conditions, instead of panicking."

Founded in 1986, Sound Sailing Center’s expert sailors introduce students to the Sound during their professional-quality classes. Their instruction philosophy ensures the proper learning environment for each student with classes that span several days with fewer students per class and a fleet equipped for single-handed sailing. The center also offers a variety of membership options.

54 Calf Pasture Beach Rd
Norwalk,
CT
US

The Boat Locker, founded in 1957, continues to furnish all manners of outdoor activities with boats and boating gear alongside an extensive stock of snowboards, standup paddleboards, and accessories. Careen across wintry slopes or down carpeted escalators atop a selection of Arbor snowboards ($299+) while outfitted in Burton boots, binding, and apparel ($20+). Standup paddleboards ($799+) surf down shores while sets of Anon goggles ($65+) shield eyes from chilly mountain breezes. The protective lenses of pairs of Kaenon, Maui Jim, Oakley and Gill sunglasses ($70+) safeguard wearers’ mugs against harsh elements when snowboarding or after accidentally falling face-first into the office koi pond.

1543 Post Rd E
Westport,
CT
US