Your Voyage Aboard SailSelinaNY
Your journey aboard SailSelinaNY begins as we glide gracefully out of Greenport Harbor, where the working waterfront blends old-world shipbuilding charm with modern maritime life. As we set sail, you’ll pass Mitchell Park Marina, the historic Greenport Carousel, and the bustling docks where local fishermen unload their daily catch. Across the channel, you’ll see the Shelter Island Ferry crossing peconic sound carrying passengers & cars alike.
As we make our way into the Peconic Bay, the scenery opens to sweeping views of Shelter Island Sound and the sparkling waters that connect Gardiners Bay to the Long Island Sound. Keep an eye out for wildlife—graceful ospreys nesting atop channel markers, cormorants drying their wings in the sun, and turns diving for fish.
Once out on the open bay, you’ll have the option to help raise SailSelinaNY II’s magnificent 1,000-square-foot gaff-rigged sail, or simply sit back and relax as the wind fills the canvas and the golden light dances across the water. With her gleaming mahogany trim and quiet dignity, this 1926 wooden yacht offers a sailing experience that’s equal parts adventure and nostalgia—an unforgettable way to experience the timeless beauty of Greenport and Shelter Island —an elegant blend of Long Island heritage and timeless nautical adventure.
Planning a sunset cruise, sailing day trip, or a weekend getaway? Just minutes away but worlds apart, Greenport, New York, is the ideal destination for your sailing vacation or getaway, offering a peaceful escape that’s just a short drive from NYC. It’s also the perfect spot for sunset sails and scenic cruises with SailSelinaNY.
Once you’re here, you’re steps away from charming pubs, world-class restaurants, shopping, wineries, the Greenport Brewery, our historic waterfront, and a variety of other activities including kayaking, golfing, biking, and our fantastic spas.
For the best weekend getaway, book a room at one of Greenport, New York lovely bed & breakfasts or stay on the water at the Sound View Inn, Silver Sands Motel & Beach Bungalows, or The Harbor Front Inn. Greenport, New York is also home to many exciting events throughout the year, like Greenport Cherry Blossom Fest, Greenport Maritime Festival, North Fork TV Festival , Reggae Fest, Shelter Island Fireworks , Fall 5K Run/Walk — Shelter Island, Floating Sound Bath & Wellness Series — Greenport, Greenport Farmers Market — Greenport (Mitchell Park), Merry Merfolk Parade — Greenport, Camp Pridwin Seasonal Celebrations — Shelter Island, and the East End Seaport Maritime Festival.
When’s the best time to sail Gardeners Bay?? It’s a tough question since it depends on the experience you’re looking for. Winds are lighter in the morning and evening, with the strongest breezes around midday. If the weather takes a turn, our captains make the call at the time of departure. Should it be unsafe or unpleasant, you have the choice of rescheduling, receiving a gift card for a future cruise, or getting a full refund.
SailSelinaNY is conveniently located at the Harbour Inn’s dock at 101 N Harbor Road in Greenport, New York. We hope to be the first name that comes up when you search for “sailing near me” or “sailboat sunset cruise.”
And yes, we are pet-friendly! Bring your furry friend along for the adventure.
After your excursion, we’ll ask for your feedback—your input helps us continue to provide the best boat ride in Greenport, New York.