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Sixty-Something: "Destination Sailing" In The 2020 Hamptons

T.J. Clemente

A recent voyage to Greenport. (Photo: TJ Clemente)

The pristine clear and beautiful waters that surround the Hamptons, along with steady breezes, makes sailing in the Hamptons special. The views rival anywhere in the world, but are especially pleasant in the summer. Besides riding the winds to get an optimal sail, I also enjoy what I call "Destination Sailing," that is leaving Three Mile Harbor, East Hampton and aiming for a port, like Greenport, Orient, Sag Harbor, Montauk, or Shelter Island, landing there, tying up, walking around, and sailing back to East Hampton all in the same day!

Practicing "safe spacing" is not a problem when you are sailing in beautiful Gardiner's Bay and the other waterways of the Hamptons. This summer, for safety, I am exclusively swimming off the sailboat at beaches where folks just cannot get to by car. The water is still cold, but I have a short sleeve spring wetsuit, something I recommend to all sixty-something folks and others who like to be comfortable when swimming in brisk temperature waters. The surfers love them.

My favorite destination to sail to is Greenport because once I tie up on Preston's Dock (free) I am in the middle of a busy sea faring town with Claudio's right there for a quick lobster roll and a beer. I sailed there just this week and enjoyed the feeling of landing on the North Fork.

Another wonderful place to dock for free is the Town Dock at Dering Harbor located on Shelter Island, next to the gas dock. I always stop there to buy fuel. Why fuel for a sailboat? Because as old uncle Don always says, every sailor eventually has to use the iron sail! The iron sail meaning the motor. Marie Eiffel's Market is there next to the Town Dock. Her market, I believe, makes the best lobster rolls on the whole East End, due to her special sauce and her great freshly baked French brioche it is presented on.

A recent voyage to Greenport. (Photo: TJ Clemente)


A little known destination is Orient by the Sea, a restaurant that has free dockage for visitors to their restaurant. Tucked in almost secretly just west of the Orient Ferry location at Orient Point, it is not that easy to find your first time there. However, once there you will discover Orient by the Sea also has a great lobster roll, along with a full diner type menu. There has always been lots of outside dining overlooking the boats. If you have never been there, you should make a point of boating over!

The Town Dock at Sag Harbor's wharf is in its final renovation stage. Docking there, even for a short while, is not free. The renovation was delayed due to the Coronavirus shutdown, so I haven't landed there yet in 2020. Hopefully soon I will because Sag Harbor has a historical charm with all those buildings and homes that date back to the 1700's! Plus, I love to gawk at the multi-million dollar yachts parked on the wharf!

Finally, the biggest challenge is trying to sail to Montauk and back all in one day. The last time I tried the winds died and I was forced to stay overnight tied up to the fuel dock at the Montauk Marine Basin. Luckily my friend, the late Carl Darenberg, the owner of the marina was there and offered for me to tie up as long as I was gone first thing in the morning. It was July 3, so we had a wonderful night in Montauk, eating at Gosman's and singing karaoke at Liar's Saloon before we headed home with favorable weather and winds on a memorable July 4th.

I can't wait for my next destination sail! I am aiming to go to Shelter Island's Coecles Harbor and tie up on the Ram's Head Inn Dock. I love strolling their grounds. They make a wonderful Bloody Mary there too! Hopefully they will be serving them by the time I get there.




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