THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend two hours aboard a private 36-ft Jeanneau in Oyster Bay Harbor with a USCG-licensed captain, stand-up paddleboard, swim platform and pool floats included. Ideal for sunset sails, casual swims, and hands-on introductory sailing on Long Island Sound.
Spend two hours aboard a private 36-ft Jeanneau in Oyster Bay Harbor with a USCG-licensed captain, stand-up paddleboard, swim platform and pool floats included. Ideal for sunset sails, casual swims, and hands-on introductory sailing on Long Island Sound.
The bow cuts through a pale-green swell as WilDSWEPT unfurls its sails and the harbor opens: a fringe of stately waterfront homes, a working marina, and the constant, bracing breath of Long Island Sound. Wind picks at your jacket; gulls wheel and the captain calls out landmarks—piers, oyster beds, a distant headland—while the boat settles into an easy rhythm.
Verified experiences and guided adventures in the surrounding area.
Operated by Windward Sailing Charters · Oyster Bay, New York
The bow cuts through a pale-green swell as WilDSWEPT unfurls its sails and the harbor opens: a fringe of stately waterfront homes, a working marina, and the constant, bracing breath of Long Island Sound. Wind picks at your jacket; gulls wheel and the captain calls out landmarks—piers, oyster beds, a distant headland—while the boat settles into an easy rhythm.
Oyster Bay Harbor sits on Long Island’s historic Gold Coast, a shoreline shaped by the last glaciation and later dotted with 19th- and early-20th-century estates. Nearby Sagamore Hill, Theodore Roosevelt’s home, anchors the town’s cultural memory, while the harbor itself remains a mix of marina infrastructure and tidal flats that host shellfish and migrating birds.
On a private two-hour charter aboard WINDSWEPT (a 36-ft Jeanneau), expect a compact, hands-on outing: a USCG-licensed captain, shaded cockpit, swim platform, floats, and a stand-up paddleboard are included. You can join the helm, sunbathe, swim off the transom, or drift and watch osprey hunt for fish.
Practicalities: the launch from Oyster Bay Marine Center delivers you to the boat; LIRR runs from Penn Station to Oyster Bay station nearby. Charters accommodate up to six guests—ideal for a short celebration or an introductory sail. Bring layered clothing (offshore wind chills the afternoon), reef-safe sunscreen, and a towel; plan an evening slot for sunset light. If you’re prone to seasickness, take preventative measures before boarding. With basic planning and the captain’s local knowledge, this two-hour outing is an accessible way to experience Long Island Sound’s shoreline energy and harbor-scene serenity.
easy.
2 hours.
Suitable for most fitness levels; basic mobility to climb a short launch ladder and move on deck is helpful
Private charters aboard WINDSWEPT accommodate up to six guests.
WINDSWEPT is a 36-ft Jeanneau and typically includes a small marine head; confirm specifics with the operator when booking.
Yes—bring snacks or a light picnic. The boat has refrigeration and a YETI cooler; alcohol policies are set by the operator so check ahead.
Take the LIRR from Penn Station to Oyster Bay station; the marina is a short walk and a provided launch service will ferry guests to the dock.
Oyster Bay’s waterfront grew during the Gold Coast era; estates and yacht culture expanded in the late 19th and early 20th centuries while native oyster harvesting shaped the harbor economy earlier.
The harbor supports shellfish beds and migratory birds; choose reef-safe products, avoid disturbing seabed habitats when swimming, and follow captain guidance to minimize wake near shore.
Windward Sailing Charters operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
The bow cuts through a pale-green swell as WilDSWEPT unfurls its sails and the harbor opens: a fringe of stately waterfront homes, a working marina, and the constant, bracing breath of Long Island Sound. Wind picks at your jacket; gulls wheel and the captain calls out landmarks—piers, oyster beds, a distant headland—while the boat settles into an easy rhythm.
The bow cuts through a pale-green swell as WilDSWEPT unfurls its sails and the harbor opens: a fringe of stately waterfront homes, a working marina, and the constant, bracing breath of Long Island Sound. Wind picks at your jacket; gulls wheel and the captain calls out landmarks—piers, oyster beds, a distant headland—while the boat settles into an easy rhythm.
Oyster Bay Harbor sits on Long Island’s historic Gold Coast, a shoreline shaped by the last glaciation and later dotted with 19th- and early-20th-century estates. Nearby Sagamore Hill, Theodore Roosevelt’s home, anchors the town’s cultural memory, while the harbor itself remains a mix of marina infrastructure and tidal flats that host shellfish and migrating birds.
On a private two-hour charter aboard WINDSWEPT (a 36-ft Jeanneau), expect a compact, hands-on outing: a USCG-licensed captain, shaded cockpit, swim platform, floats, and a stand-up paddleboard are included. You can join the helm, sunbathe, swim off the transom, or drift and watch osprey hunt for fish.
Practicalities: the launch from Oyster Bay Marine Center delivers you to the boat; LIRR runs from Penn Station to Oyster Bay station nearby. Charters accommodate up to six guests—ideal for a short celebration or an introductory sail. Bring layered clothing (offshore wind chills the afternoon), reef-safe sunscreen, and a towel; plan an evening slot for sunset light. If you’re prone to seasickness, take preventative measures before boarding. With basic planning and the captain’s local knowledge, this two-hour outing is an accessible way to experience Long Island Sound’s shoreline energy and harbor-scene serenity.