Spend a Day on the Water with Sail Montauk

While we marvel at all the powerboats and yachts that parade through the waters of the East End, there’s something special about turning off the motor and letting the wind take you away.

The folks over at Sail Montauk know a thing or two about maximizing your sailing experience. Husband and wife team Darius and Alexandra Ali captain the sailboats and offer a variety of ways for sailors to spend their time on the water.

Located on the north side of Montauk, Sail Montauk primarily takes passengers out on Block Island Sound, Fort Pond Bay and Lake Montauk. “Fort Pond Bay is one of our favorite destinations, and is even good for anchoring and swimming,” says Alexandra, who goes by Ali. “Flat water with lots of wind is what sailors like.”

The plethora of smooth sailing spots at the end of Long Island make Montauk a great place for both masters and nautical novices. However, Montauk is known for its fishing, so you need to be mindful while sharing the water with some of those determined fishermen. But don’t let that discourage you from giving it a chance.

“Being a ‘blow boater’ or ‘rag hanger’ (as the locals refer to us sail boaters) has its ups and downs,” Ali says. “It’s a drinking town with a fishing problem, so naturally powerboats outweigh sailboats. But even so, it’s the people that make Montauk a great place to sail.”

Don’t know how to sail? In addition to private lessons, Sail Montauk offers a Basic Keelboat Sailing two-day course, as well as a junior sailing program for kids.

Sailing may seem intimidating at first, but experts like Ali say it won’t take long for you to get the hang of it. “Sailing is easier than some may think,” Ali says. “Once out on the boat, it makes more sense, it’s definitely a learn-by-doing sport. At first people tend to get hung up on the jargon, but once you understand how your boat works with the wind, everything else will fall into place with practice.”

What if you just want to be at ease on a sailboat without having to worry about the wind? No worries, Sail Montauk offers a handful of private charter options that are hands on—you can do as little or as much as you’d like. To make the deal even sweeter, each sailboat has a cooler stocked with ice, water and Honest Tea. The sailboats are BYOB, and you are encouraged to sip an iced cold drink while you soak up the sun. You can also play your own music by connecting your phone to the speakers onboard.

During the day, you can go out for a two-hour Taste of Sailing to get the feel of being a part of the crew. The three-hour Sail and Swim charter gives you the chance to learn some basics and stops so you can dive in and enjoy the refreshing water on a hot day. There are water guns, noodles and other items that come with the boats to turn it into a day full of family fun.

If you’re looking for a little romance on the water, the Sunset Sail is a perfect way to end the day. Nothing beats watching the sunset light up the sky as you coast along with a glass of champagne in hand.

If you really want to have a party at sea, Sail Montauk offers Flotilla Boat Parties for larger groups to book multiple boats and sail side by side. For experienced sailors, you can charter your own Catalina 22 sailboat for half the day and set sail.

Fishing may still rule the day in Montauk, but sailing provides a fun and interactive alternative. As Ali says, “It seems like the sailing scene grows just a little bit more each season, and we’ve been discovering Montauk has its fair share of closet sailors.”

Sail Montauk operates out of the Montauk Yacht Club at 32 Star Island Road, Slip 412. For more information, visit sailmontauk.com.