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Desirable Destination: Montauk, Long Island

Fallin' for the East End | September


It amazes me that no matter what the weather forecast is on Labor Day weekend, Long Island’s South Shore waterways are jam packed. It appears that this is everyone’s last hurrah of summer. Then on the Tuesday following this long weekend, the sounds of TraveLifts hauling boats for winter storage reverberate from East Rockaway to Amagansett. But just because September marks the end of summer, that doesn’t mean it’s the end of boating for the year. In fact, it’s one the best times to explore a boater’s heaven called Montauk.

This “quaint drinking village with a fishing problem,” according to the T-shirt available from the town’s fish-tale-filled Liar’s Saloon, is a summertime seaside tourist mecca. Montauk lies at the tip of Long Island’s South Fork, where it juts out into the Atlantic Ocean and Block Island Sound and is easily accessible by boaters from both southern Long Island and down the coast. Growing up on the South Shore (and spending a lot of my down time out here), I favor Montauk at this time of year. There are many reasons why.

The first is why this place is famous: fishing. In September the waters offshore are still warm and offer opportunities to chase tuna, swordfish, and other hard-fighting, good-eating pelagics at the nearby canyons. I do at least one fall trip out here each year to fill my freezer with steaks and fillets. And if you don’t feel like using your own boat, there are plenty of charter boats. Coastal fishing is also good, with light-tackle game like striped bass just off Montauk’s famed lighthouse.


That lighthouse, by the way, has a storied place in local history. It was the first one in New York and is the fourth-oldest working lighthouse in the country. Construction was authorized by the Second Congress in 1792 under George Washington and was completed in the fall of 1796. There are 137 steps to the top, and its 2.5-million-candlepower light can be seen up to 19 nautical miles away. So even if your boat’s GPS goes wacky, you should be able to find safe entrance to Montauk harbor--just follow the high beam. I’ve been in the lighthouse, and it offers the best view in Montauk (although I don’t recommend looking into the light).

The local restaurants, bars, and colorful characters (Liar’s Saloon, again) that are Montauk can make for a great off-season, on-the-water retreat, but there is pampering available these days, too. Well-known inns such as Gurney’s, which I used to visit with my family as a kid, now offer everything from a fitness center to facials to full-day spa treatments. Ah, what better way to treat your significant others after they have agreed to spend the morning catching cow-size bass with you than with a facial and a thalasso bath?

There’s also shopping at boutiques both in town and the ever-expanding Gossman’s dock, which has several eateries that offer views of the harbor and great seafood. I’ve spent hours here just watching boats pass in and out of the harbor while my food got cold and my beer got warm. If you really want to end the day in style, make a call to Montauk’s Deep Hollow Ranch and ride horses on the beach during sunset.

So call off the TraveLift, fuel her up, and point the boat to The End. It could be the beginning of some of your year’s best boating.

Desirable Destinations

January: British Virgin Islands
February: Great Abaco Island / Bahamas
March: Little Harbor Cay / Bahamas
April: Los Sueños / Costa Rica
May: Monaco
June: Massachusetts
July: Washington, D.C.
August: British Columbia
September: Montauk, Long Island
October: Hudson River, New York
November: Half Moon Cay / Belize
December: St. Barts

This article originally appeared in the December 2006 issue of Power & Motoryacht magazine.