Sailing and boat tours in Greenport, Oyster Bay, Oakdale and Montauk

A private escape awaits at Long Island's sailing ports whether you lock in a tour, an educational cruise or a sunset sail.

SAIL WITH A SUNSET

ABOARD Christeen, a restored oyster sloop from The WaterFront Center in Oyster Bay

The view from the 60-foot sailboat includes Gold Coast mansions lining Centre Island. A U.S. Coast Guard-certified captain helms the ride through Oyster Bay Harbor and Cold Spring Harbor. You’ll learn about the history of Christeen, built in 1883 in Glenwood Landing and a National Historic Landmark since 1992.

WHEN | WHERE 6 p.m. sunset cruise most days through Labor Day ($55) from 1 West End Ave., Oyster Bay, reserve online. The center offers other sailing experiences, including a two-hour harbor tour ($45), marine ecology cruises ($35). Private charters available (starting at $1,500).

MORE INFO sailchristeen.org, 516-922-7245

SAIL WITH A SWIM

ABOARD The Mon Tiki fleet of catamarans in Montauk 

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 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. There's plenty of time to take a plunge into the water from the vessel's swim ramp and paddleboards (life jackets provided). Two- to three-hour private sails start at $275. 

WHEN Through early October

MORE INFO sailingmontauk.com, 631-668-2826

SAIL AND SIGHTSEE

ABOARD Priscilla, a restored 1888 oyster sloop from the Long Island Maritime Museum in West Sayville

The Long Island Maritime Museum's historic oyster sloop Priscilla hosts two-hour cruises on the Great South Bay. Most sails have included vouchers for lunch or dinner at The Snapper Inn restaurant in Oakdale. Sails include 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. It became a National Historic Landmark in 2006.

WHEN | WHERE 4 p.m. Tues. sail only: $45 ($20 ages 12 and under); 4 p.m. Wed.-Fri. dine and sail ($80, includes $35 food voucher; $20 ages 12 and under, no food voucher); 1 p.m. and 4 p.m. Sat.-Sun. ($80, includes $35 food voucher; $20 ages 12 and under, no food voucher). Registration is required. Arrive 30 minutes before sail time at the dock behind The Snapper Inn restaurant, 500 Shore Dr., Oakdale.

MORE INFO sailpriscilla.org, 631-854-4974

SAIL AND JAM 

ABOARD The Moon Chaser in Babylon 

Get ready to rock out with a live band that performs a full concert on the top deck of a 65-foot boat, for a three-hour evening cruise on the Great South Bay. A hot food buffet and soft drinks are provided while a cash bar is available to purchase cocktails. Music ranges from classic rock to reggae to ’80s pop to various tribute bands for a crowd that maxes out at 200 people. $58, ages 21 or older.

WHEN | WHERE Fridays, Saturdays and Sundays, May through October (times vary); Captree State Park, 3500 E. Ocean Pkwy., Babylon

MORE INFO themoonchaser.com, 631-265-1848

SAIL NEAR SHELTER ISLAND

ABOARD Layla, a 45-foot sailboat docked in Greenport

Capt. Liz Gillooly leads private sails from Greenport that explore the waters around Shelter Island. Options include shorter morning and sunset sails (from $750 for a private charter up to six passengers) and traditional half-day charters. Guests may bring their own snacks and drinks, catering options available.

WHEN | WHERE June 1-Sept. 15 (times vary); Safe Harbor Sterling Marina; 1410 Manhanset Ave., Greenport, Dock H11

MORE INFO 631-319-0161, laylasailing.com