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Summer Pleasures: Sunset Sailing on Lake Montauk

Sail Montauk Captain and crew
Sail Montauk Captain and crew

If you’ve ever dreamed of sailing off into the sunset but don’t know port from starboard perhaps it’s time to check out Sail Montauk’s Tuesday night summer regattas.

Sail Montauk is located on Star Island just off West Lake Drive on a pier in at the Montauk Yacht Club. They have a fleet of four Catalina 22s available for charter, lessons or you can plunge right into the sailing experience by signing up to help crew on one of the Tuesday night regattas—no experience necessary.

Darius Ali is the Captain. He learned to sail on Lake Montauk and left New York City after a stint working in medical billing to start up Sail Montauk.

Tuesday night marked the kick-off of the Tuesday night regattas for the summer of 2014. Fifteen people arrived with various degrees of sailing savvy and Darius assigned them to crew for his four captains. The October Rose—better known as the Montauk Water Taxi—accompanies the racers out to the middle of the lake for those who’d rather watch the races and enjoy the sunset without getting their hands wet. The water taxi is also a great option if you want to bring a picnic or just hang out and watch the sun setting over Lake Montauk.

The Catalinas and the Water Taxi are berthed behind the Montauk Villas and each one is helmed by a licensed skipper. Upon arrival each guest is briefed in the basics of sailing: port (left,) starboard (right,) and tacking (the maneuver of turning into the wind between starboard and port tack) as well as basic sailing safety.

Just after 6 p.m. the boats, accompanied by the water taxi, left the slip. There was a brisk wind ruffling the lake and the temperature quickly dropped as the boats made their way out onto the water.

The next two hours passed quickly as the spectators enjoyed complimentary beer and ice tea while cheering on the boats.

Darius had set up the course beforehand by stringing up giant buoys into a large triangle. At the start of each race the boats must each pass through the start line by tacking back and forth until the signal is given. The four boats must make the loop of the buoys, without touching each other, three times.

On Tuesday night the boat captained by Ali Spoelstra, who is engaged to Darius Ali, won with two first place finishes and a second. The boat was nicknamed the “Pink Ladies” as it was all girls.

After the third race the boats made their way back to the marina, it was just after 8 o’clock. The wind had dropped considerably and the sun was sitting almost at the horizon.

The Montauk Sail regattas are held every Tuesday night during the summer at 6 p.m. The cost is $95 per person. Sail Montauk is an ASA affiliate. Charters, lessons and sail and swim packages are also available. For additional information visit Sail Montauk.

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