Long Island is, well, a Long Island....

Blown Away Too at Sunset Harbour in East Patchogue
Ben Amato
Wherever in the world you live, life takes on a different flavour when you see it from the water. Ben Amato lives on Long Island, New York, and has been sailing those waters for 40 years. Currently he sails a 32-foot catamaran, Blown Away Too.

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.


Stone jetty at Moriches Inlet looming ahead
Ben Amato

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.


Montauk Yacht Club
Ben Amato

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 Montauk
Ben Amato

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.

Ancient stone fortress The Ruins on the north side of Gardiners Island at Bostwick Point
Ben Amato

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.


Radar Dish at Montauk
Ben Amato

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 thi