Summer in the Hamptons – New York to Long Island Sound


Sailing up the East River, under the Brooklyn Bridge and past the United Nations, we headed out of NYC for Long Island Sound (LSI) on Friday, July 28.   Rowland and his beautiful, bright daughter Savannah had rejoined us as we began our new adventure of exploring the small towns on Long Island including the Hamptons.

map of long island (2)

Long Island Sound

72817 up East river beneath Brooklyn bridge

Sailing under Brooklyn Bridge, NYC

Port Jefferson, LI, NY

First stop was Port Jefferson, a town that was recommended to our daughter Emily by a co-worker that lives on Long Island.   With high winds forecast the next day for LSI, we opted to spend an extra day in Port Jefferson and we were glad we did.  It’s a lovely little town that was filled with summer tourists.  I hate to admit it, but my most vivid memory of Port Jeff will be of the fabulous bread pudding we found in a little spot called Sweet and Savory which had at least 20 flavors…almost as good as Izzy’s ice cream back home.   Savannah was only able to join us for a day, so she caught a ferry back to the mainland later in the afternoon.

72917 minne in port jefferson NY

Port Jefferson and Minnehaha

72917 port jeff on long island sound NY

72917 rowland patriots fan

Who let this New England Patriot’s fan onboard

72917 with sunset port jefferson NY

Minnehaha at Sunset in Port Jeff

Sag Harbor, LI, NY

Sag Harbor was our next destination, with its reputation of being a summer haven for wealthy New Yorkers to escape the city’s summer heat.   We refueled for the first time since leaving Miami in May (you can go long distances when you spend most of your time under sail versus engine power) and as it turned out, winds died and we ended up motor sailing most of the way.  First a stop at Orient Point, at the most eastern point on the northern shore of Long Island (LI) to drop Rowland off so he could catch a ferry and head towards home in Connecticut.

73017 cookin bacon on sailto sag harbor

Cooking breakfast on the aft deck

73017 hunting pesky flies

Tennis?? No. Killing a sudden influx of biting flies with the zapper.

73017 doug returns from drop rowland@ ferry

Doug returning in the dingy after dropping Rowland at the ferry

73017 goodbye Rowland...miss you

Good bye Rowland, Hopefully we’ll see you in Newport

73017 along sail to sag harbor

Light house on Long Island Sound near Orient Point

Hard to believe, but after all this time it was the first time that Doug and I were truly on our own sailing.  Time for the ‘little birds to leave the nest’ and the security of having an experienced captain on board.  I hoped that our first ‘flight’ would not be as difficult as these little birds have when they leave a nest in the video below.

In terms of weather, Sag Harbor did not disappoint.  Gorgeous, bright, summer days with a mild breeze and no humidity—completely understandable why someone would want to spend their summer there.  Sag Harbor is a small town, towards the end of LI, whose population swells in the summer as well as the traffic.   We arrived on a Sunday and there was a steady stream of helicopters flying out of the area-  undoubtedly bringing residents back to the city from their weekend vacation home.

Safely tied to a mooring ball, and relaxing on our aft deck, we saw our bigger beautiful ‘sister’ Nala, HH 66-03, sailing into the harbor.  Sag Harbor is Nala’s summer home port.   It was the first time that an HH55 and HH66 catamaran were together in the same location anywhere in the world, other than the factory in China.  Of course, we had to head over and say ‘hi’ to the captain.



We spent a few days in Sag Harbor, exploring the town, doing laundry (same drill, different laundromat), and relaxing.  Sailing is popular in these parts and kids start learning early.   We loved sitting on the boat while the classes would sail around us in their little ‘Optis’ (short for Optimist) -boats that are designed and used extensively for teaching kids to sail. The youngest age group reminded me of soccer games of 5 and 6 year old kids – they all seem to be confused and congregate together in one location on the course.

8317 dering harbor shelter island sail school

Sailing school- getting positioned for a race

8317 dering harbor end sail school

Sailing school over- ‘little ducks’ get towed back to shore

Shelter Island, LI, NY

On Wednesday, we pulled up anchor and headed for Shelter Island.  Shelter Island is only short distance from Sag Harbor and can only be reached by boat.   We took advantage of the 15 mph winds and took the long route to the island.   We had decided, before we left Sag Harbor, that we needed to get more exercise and should have paddle boards (well, OK, the exercise was an excuse for a new toy).   Chris, who had been our HH commissioning captain in Florida had a friend with a paddle board shop in Greenport, which was right across the channel from Shelter Island.   Once anchored we fired up the dingy and headed to Greenport to get our inflatable paddle boards.  We had decided on the inflatable (SUP) types because they are easier to store onboard.

Shelter Island, day 2, started with our first attempts at paddle boarding- successfully, albeit slowly, I might add, followed by a bike ride around the island.  I loved Shelter Island.   Very limited development, with lots of fields and tree-covered country roads.  We were told that Billy Joel had a home there but alas, no Billy Joel sightings.

During the previous night, a 208 ft. mega yacht named Vibrant Curiosity had sailed into the channel between  Shelter Island and Greenport, well within spying range of our binoculars.  Around 5:00 in the afternoon we watched as a helicopter descended and landed on the back deck.   For those of us living in a different region of the country, not to mention income strata, it was exciting to see.  Try as I might, the binoculars were not strong enough to get a good view of who was dropped off.  Just call me the neighborhood snoop.

8317 Vibrant Curiosty @ shelter island NY

Shelter Island with Vibrant Curiosity mega yacht



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