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Long Island cruises with wine, music and trivia contests

First Mate Jessica Drennan, of Rockville Centre, runs

First Mate Jessica Drennan, of Rockville Centre, runs the trivia contest last month on the Freeport Water Taxi & Tours evening cruises. Credit: Marisol Diaz

This summer one of Long Island’s most romantic traditions has a creative twist: sunset cruises that spice up the dazzling show on the horizon with a little wine, trivia or song.

Passengers on these specialty cruises can opt to taste wines from one of Long Island’s oldest vineyards, test their memories in a floating trivia contest, or move to the music as popular cover bands play on deck.

Here are sunset cruises that will add a toast, a laugh or classic tunes to the end of a summer day.


WHEN | WHERE Tuesdays through Aug. 29, departs between 7 and 7:30 p.m. (depending on sunset) at Freeport Water Taxi & Tours, 211 Woodcleft Ave., Freeport

INFO 516-874-4082,


Set sail for a floating game show that will test your memory for trivia in a variety of subjects. Aboard Freeport Water Taxi’s 44-foot yacht, contestants are asked to form teams for three rounds of questions. You’ll be quizzed in categories including movie titles, 1980s songs and sports awards, says Emily Cohen, one of the hosts. You’ll also be asked to identify photos of anything from famous monsters to famous mustaches.

“The emphasis is definitely on fun and laughter, and being goofy,” Cohen says.

Prizes are given on out each trivia cruise and winners’ names will are entered into a drawing for a catered sunset cruise for 28 people.

As a bonus, there’s quite a view as your ship cruises around Jones Beach, Freeport and Point Lookout.

“On clear nights, in the distance you see One World Trade Center and most of lower Manhattan,” says Cohen’s father, Freeport Water Taxi skipper Rick Cohen.

ALSO TRY Freeport Water Taxi also does a wine and sprits-tasting sunset cruise on Thursday nights through Aug. 31 ($25).


WHEN | WHERE 6 to 8 p.m. July 21 and Aug. 11, from the 103 Third St. dock, Greenport

INFO 631-734-7537,


Toast a glorious East End sunset with a fine vintage aboard the 80-foot Peconic Star Express. Bedell Cellars of Cutchogue, a family-owned winery known for handcrafting wines in small batches, pours reds, whites and roses.

The view is “gorgeous — they take us around Peconic Bay and Shelter Island,” says Molly Deegan, Bedell’s executive vice president of marketing. Peconic Star Express Capt. Dave Brennan says the sights include the Long Beach Bar lighthouse, a beloved local landmark known as the “Bug Light.”

Looking to pair your beverage with something savory? Stop at the onboard raw bar stocked by Little Creek Oyster Farm and Market in Greenport, or the antipasto served up by Lombardi’s Love Lane Market in Mattituck.


WHEN | WHERE Select Fridays to Sundays through Sept. 16 aboard The Moon Chaser, departing from Captree State Park, Babylon.

INFO 631-265-1848,

ADMISSION $40 to $55

Whether you like Sinatra, reggae, the Eagles, The Grateful Dead or Jimmy Buffett’s “Margaritaville,” you can dance until the stars come out on a series of summer cruises featuring live music by local cover bands.

The Moon Chaser, a 65-foot vessel is more or less a seagoing bar-restaurant. Find a seat on the fully enclosed main deck or the canopied upper sun deck to enjoy the sea breezes on the Great South Bay, past the Fire Island Lighthouse, to Fire Island Inlet.

The $49 cruises include beer, wine, soda and a hot buffet catered by Marconi Manor, of Islip. A mixed drink can be purchased at the bar for $8.

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