Long Island sailing and boat tours in Greenport, Oyster Bay, Oakdale and Montauk
Yacht Charter Pro organizes 4-hour private boat tours in the Hamptons aboard a 55-foot yacht. Credit: Shaun Photography
On sailboat cruises from Oyster Bay to Montauk, you can relax on deck, cooled by sea spray and a glass of wine. Or you can get up off your cushion and join the hands on deck in Oakdale.
Here's how to get a taste of cruising on Long Island's waters, whether destined for a swimming hole or merely a photo-worthy sunset to a summer day.
SAIL NEAR SHELTER ISLAND
ABOARD Layla, a 45-foot sailboat docked in Greenport
INFO 631-319-0161, laylasailing.com
Captain Liz Gillooly leads up to six passengers on private sailings from Greenport that explore the waters around Shelter Island. Options include shorter morning and sunset sails (from $700) besides traditional half- and full-day charters. Guests may bring their own snacks and drinks.
SAIL WITH A SUNSET
ABOARD Christeen, a restored oyster sloop from The WaterFront Center in Oyster Bay
WHEN | WHERE 6 p.m. most evenings through Labor Day ($45 a person) from 1 West End Ave., Oyster Bay, reserve online. The center offers other sailing experiences, including a two-hour harbor tour. Private charters available ($975).
INFO 516-922-7245, thewaterfrontcenter.org
The view includes Gold Coast mansions lining the tony Centre Island on cruises aboard the 40-foot sailboat. A United States Coast Guard-certified captain helms the ride through Oyster Bay Harbor and Cold Spring Harbor. You’ll learn about the history of Christeen, a National Historic Landmark built in 1883 in Glenwood Landing.
SAIL WITH A SWIM
ABOARD The Mon Tiki fleet of catamarans in Montauk
INFO 631-668-2826, sailingmontauk.com
The 65-foot Mon Tiki Largo, the 40-foot Mon Tiki and the 26-foot Mon Tiki Mini — all catamarans — are playfully named after explorer Thor Heyerdahl's Kon-Tiki. Amelia Ryan, who owns and operates the line with her husband, Capt. David Ryan, says the cruises explore a world beyond the currently chic resort community. "All of that falls away when you are out on the water with the sounds of the wind, the waves and the natural beauty," which occasionally includes dolphin sightings, Ryan says. Passengers can bring their own lunch and beverages on a two- to three-hour private sail (starting $250) through early-October and there's plenty of time to take a plunge into the water from the vessel's swim ramp and paddleboards (life jackets provided).
SAIL AND SIGHTSEE
ABOARD Priscilla, a restored 1888 oyster sloop from the Maritime Museum in West Sayville
WHEN | WHERE 4 p.m. Tuesdays-Thursdays, $45 ($20 kids) or dinner sail 4 p.m. Fridays, 1 and 4 p.m. Saturdays-Sundays ($75 includes $30 food voucher), reserve online. Arrive 30 minutes before sail time at the dock behind The Snapper Inn Restaurant, 500 Shore Drive, Oakdale.
INFO 631-854-4974, limaritime.org
The Long Island Maritime Museum's historic oyster sloop Priscilla hosts two-hour cruises on the Great South Bay. Some sailings have included options for lunch or dinner at the Snapper Inn restaurant in Oakdale. Sails include plenty of narration that covers the ship's history among a 500-boat fleet that plied the South Shore bays for oysters. The vessel was retired in the 1960s and restored in 2002.
CRUISE THE EAST END
ABOARD A 55-foot power yacht
WHEN|WHERE By reservation, custom trip departures include Hampton Bays and Sag Harbor for half- or full-day experiences (from $3,500 for 4 hours)
INFO 631-599-8048, yachtcharterpro.net
Captain Allison Edelstein leads groups of up to 8 people on private cruises around East End waterways that could include stops at Sunset Beach on Shelter Island or Greenport. Trips include use of 8-foot water floaters and a Jet-Ski with soft drinks, water and towels at your disposal. Edelstein curates VIP add-ons such as catered food onboard or waterfront dining at a restaurant.
