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Itís A Really Long Island

Originally Posted: September 18, 2008

Ben Amato

The 'Blown Away Too' at Sunset Harbor in East Patchogue ready for the trip. Photos
by Ben Amato

I've always wanted to see if I actually live on an island, even though it is called Long Island. You commute on the highways, visit the malls or trek into the city and you forget that the shoreline, the beaches and the waves encircle us. My crew and I aboard my catamaran sailboat went completely around Long Island and came to realize it is really long. It took eight days to travel 226 nautical miles, including several stops between Montauk and Manhattan, eight drawbridges, a dozen or so lighthouses, two thunderstorms and crossing paths with one fin in the Atlantic - a sunfish - but I swear I heard the theme music to "Jaws" the whole time we circled it. Here is the first part of our journey.

Casting away the lines which held me to the Sunset Harbor Marina, in East Patchogue was a bit scary. Instead of my natural tendency to compromise and head out for another weekend trip or day sail, it was time to face the unknown and take the first step towards "The End," as Montauk Point is called. The cozy confines of the Great South Bay were replaced with a cathartic exit through Moriches Inlet. People have died there. I've had boats for over 40 years and for the last 30 have lived within six miles of this outlet to the Atlantic. Yet I never ventured beyond the stone jetties and into its ripping currents and breakers until the second day of this odyssey.

The stone jetty at Moriches Inlet loomed ahead.

Inspiration and preparation produced a lot of perspiration, for just moments before we broke free from the inlet's grip, only a wall of white water loomed ahead of us. On the right was the too near Fire Island shore, to the left the breakers and then all of a sudden, up ahead to the south was a channel. There were some swells, one dip of the boat's bow and then we were in the calm Atlantic Ocean. You go through Moriches Inlet, and there's some turbulence and rocking down below and then you're out in open waters before you know it.

The allure of sailing is the sound and sight of being pushed through the water with only canvas, lines and skill to drive you. There is an "ancient" feel to it, making headway without the technology that fills most of our lives. The fear with sailing is that in any confrontation, the ocean wins. So the trick is to avoid conflict through patience, practice and the good sense to buy every nautical toy there is that might keep you afloat, including, but certainly not limited, to a Global Positioning System (GPS), laptop charting programs, automatic pilot, an inflatable life boat, EPIRB personal locator beacon, transponders, radar, sonar, flares, photon torpedoes, and phasers.

The cruisers at Montauk Yacht Club tied to the docks.

And then you plan - there are books to read and guides to ponder. The "Eldridge Tide and Pilot" book offers invaluable information about currents, tides and courses to take. On the paper charts or the mapping program on my laptop, you move your pencil or mouse and visualize your voyage and pleasure. But once underway, the BlownAway Too's Garmin GPS becomes the guide, for along with reporting the course and speed it also indicates every shipwreck, submerged rock and sea monster you will encounter along the way. Sailing is filled with contrasts, tensions between fulfillment and fear, ropes and readouts, sails and software.

The Great South Bay, the Atlantic, Block Island Sound, Gardiner's Bay, Plum Gut, the Long Island Sound, Hell's Gate, the East River, New York Harbor and then back to the Atlantic and home. Some boaters will read this list and cringe. Others will drool over the course while some will wonder why the rush to take all these beautiful waters in just eight days. This circumnavigation was a voyage of discovery, an exploration for future places to visit and linger at.

Commercial fishing vessels in Montauk.

Montauk Harbor is a fisherman's home, where outriggers, coiled nets, and fish traps provide the dockside restaurants the daily catch and tables filled with happy diners. The Montauk Yacht Club on Lake Montauk was our home for the evening. They had us amid the mega-yachts and towering sport fishing cruisers, so clean, new and beautiful compared to the hardened hulls of the fishing trawlers which populate the other side of Star Island. Between these two stood the Coast Guard Station, a brick house of stability in the busy harbor. The wealth and glamour of the Yacht Club had its perks - fine dining, luxurious rooms, a spa, three swimming pools (both indoor and out) and other amenities that illustrate how five stars are earned. But the blue collar feel of the fishing boats tasted like an ageless era gone by, when rods and reels were all you needed for a day on the water, rather than laptops, a Blackberry, and sunblock.

Gardiner's Bay, the Island and the legends dominate my thoughts about the sail between Montauk and Greenport. We skirted the shore of this mysterious island, once a plantation paradise for the original owner Lion Gardiner. In 1639 he purchased it from his good friend Wyandanch, the shaman of the East End tribes, and also received a Royal Grant from King Charles I, establishing it as the first English settlement in New York State.

The ancient stone fortress called "The Ruins" that juts out on the north side of
Gardiner's Island at Bostwick Point.

The Pirates of the Caribbean did not spend the summer down in southern waters off of America's coast. They visited New York and Gardiner's Island, both safe harbors where privateers and pirates could get provisions, new crew and a place to bury their booty. A monument stands on this island to Captain William Kidd, erected by his friend John Gardiner, the third Lord of the Manor. It commemorates the spot where the fabled Captain buried his treasure.

Over the centuries the Gardiner's have seen military invasions by two separate British fleets during the Revolutionary and War of 1812. During Prohibition, their island became a warehouse and haven for another sort of pirate, the likes of Al Capone and Dutch Schultz. Their offshore booty traveled through the East End towards the speakeasies of New York.

The Second World War militarized the East End, symbolized by the gigantic radar dish that still stands at Montauk Point. But just as impressive is the ancient stone fortress called "The Ruins" that juts out on the north side of Gardiner's, at Bostwick Point. Though a target for practicing pilots and gunners, it withstood those years to still protect this refuge from poachers, pirates, and prying eyes. No one is allowed on this island, six miles long and several wide. What remains of the original buildings, now hundreds of years old, or the Captain Kidd monument itself? Even the vast resources of Google could not produce even the text of what is written on the plaque or an image of the monument itself.

The radar dish at Montauk Point.

Southeast of Gardiner's, the sailing was easy. When close to shore, the wind stopped and so did we, for a swim, some lunch and a glimpse of a mystery island I would love to set foot upon. North of the island, our wind and course resumed and Shelter Island and Greenport loomed ahead.

The East End of 2008 is strangely devoid of power boaters, with dozens of sails dominating the seascape. But that changed when we arrived in the bustling harbor of Greenport. Every dock space and slip was filled with happy power boaters, drinks in hand, but they were swapping stories rather than making new ones.

The Town Dock at Mitchell Park is in the heart of the town itself. Pulling into the slip was like parallel parking on Main Street, which was just on the other side of the carousel. At dusk on this near perfect sailing day, as we were tying up the last of the lines, the park before us became an outdoor theater, with hundreds watching the opening scenes of Shakespeare's "Comedy of Errors". We had appetizers at Claudio's and ice cream under a full moon but more importantly, Greenport made us feel like we were at home, or at least what we would have loved for a home.

Shakespeare on the water at Mitchell Park in Greenport.

Three Mile Harbor was the next destination and back-tracking from Greenport to East Hampton seemed to be measured in years traveled into the past rather than miles. Again, sails cluttered the horizon and 20 and 30-year old sloops and ketches cruised with us or crossed out path. The forests of Shelter Island reached down to the water. The homes were massive, perched atop the bluffs or occupying an entire small valley. But this day was meant for the water and wind and arriving very early to Three Mile Harbor's jetties, we turned and joined another pack of sails headed north, to enjoy another hour of a freshening breeze.

Three Mile Harbor is a wonderful example of the East End's different faces. On the eastern shore were the marinas, fine restaurants and resorts. On the west were hills and bluffs dotted by beautiful estates and homes. To the south was the busy inner harbor, every inch filled with power cruisers, yachts and tall masts. To the north was Sammy's Beach, low sandy dunes and brush, exactly as it has been since the first colonists arrived. With a setting sun from a town mooring in the middle of the harbor, it was the dozens of sailboats that surrounded us that took our breath away.

East Hampton marked the halfway point in the trip around the island. The rest of the trip would be towards civilization and city sailing. The pristine harbor that morning was still. I noticed a man rowing a skiff.

Sunset at Three Mile Harbor.

"Good morning," I called out. "You look very happy."

"I am," he answered, not missing a stroke.

"How come?"

"Last night I danced with Signorey Weaver," he answered and his oars dug a bit deeper and his stroke seemed more youthful.

The waterside of the East End can be a magical place, whether docked in a small town, a luxury resort or anchored at nature's edge. Out here anything is possible and with a little luck, you could be dancing with a star.

Appeared In: lifestyle >> on the water