Cruising Western Long Island Sound, #25-36
- sondrawinter
- Sep 7
- 5 min read
Updated: 2 days ago
Friday, August 29 through Thursday, September 4
36 nautical miles (NM) / 41 statute miles
Utopia only moved once this past week: from Port Jefferson to Port Washington, but Jimmy and I, along with the crew of Quest II, took a couple side trips by land to two very different places.

Village of Port Jefferson, NY
Thursday, August 28 – Saturday, August 30

Our remaining days in Port Jeff were spent mostly with the crew of Quest II. They arrived Thursday afternoon and we enjoyed a dinner together at Fifth Season. Friday morning the pump out boat came by, and we had Utopia’s holding tank properly pumped out. Friday night dinner was hosted by Quest II, and on Saturday Cam and Denise came to visit Baxter for happy hour.
Port Jefferson to Port Washington
Sunday, August 31
36 NM
Although no wind was in the forecast, we raised the sail before slipping from the mooring ball, and just after 8:00 a.m. we headed out of Port Jefferson Harbor. Luck was not on our side and the forecasts held true with the largest wind gust seen at 8 knots. Keeping a sail up, even when the wind is too light for propulsion it helps balance the boat creating a smoother and more comfortable ride. The jib was deployed for a couple of hours when the wind was above 4 knots.
It was a special treat to see the skyline of Manhattan rise out of the horizon as we approached the entrance to Manhasset Bay. Right before turning south into the Bay, we could see two suspension bridges (Throgs Neck & Whitestone) in the distance that span the East River.
Shortly after 2:00 p.m. we had the anchor settled. Our fatigue from motor-sailing all day was punctuated by boaters on two nearby boats with poor seamanship yelling at Quest II as they tried to find a spot to drop anchor near us. We could hear strong New York accents yelling things like “You’re too close!” and “Go over there!” Maybe it is just our southern backgrounds, but the four of us were surprised at their attitude. The first two places they selected appeared perfectly acceptable to Jimmy and me. Eventually Quest II found a place close to us, and away from the yelling boaters.
Port Washington, NY
Sunday, August 31 – Thursday, September 5
After we all tidied up our boats and refreshed ourselves (ah, the magic of having an abundance of hot water readily available after running the engine for six hours!), we popped over to Quest II for a John Kretchmer Happy Hour. He discussed Heaving-To, something we did a lot on About Time, but ashamedly admit that we have not done so on Utopia. We really do need to practice this maneuver and find a way to hold the self-tacking staysail in place.
Of course, as usual, we took walks around the area. We found this area to be fairly urban and not as touristy. I liked the feel of the town, although I find it lacking proper nature trails. One morning our walk ended at a local bagel shop in which we felt rather compelled to have a second breakfast.
A pair of swans visited Utopia one afternoon and this time Baxter was up on deck for the encounter. He was extremely curious about these large birds and kept putting his front paws over the toe rail. One swan hissed at Baxter, so we had to hold on to Baxter to keep him away from the gunwale (edge of the boat).
On Labor Day, I made a point to not do any boat projects during the day. In the afternoon we got together on Quest II to grill a delicious dinner.
Side Trips by Land
Village of Roslyn
On Tuesday the four of us took a bus to the little Village of Roslyn and strolled around. This area received its first settlers in 1643. It was a cute little village.

New York City

The highlight of our stay at Port Washington was taking a day trip to New York City. The four of us took a dinghy to shore, then a bus to the Port Washington train station in time to catch the 8:30 train to Penn Station. The 45-minute ride collected commuters from Port Washington and Great Neck to Manhattan. It was interesting to note how extremely different the west side of Long Island (our train went through Queens) is compared to the eastern end (Montauk)!
From Penn Station we headed north and had bagels for breakfast before walking on the High-Line in the Chelsea area. This is a former elevated train track converted into a greenway and is about a 1.5 miles long, plus some spurs. It offers a unique view of the city and the Hudson River from a pretty park-like setting.
In the afternoon we grabbed a slice of pizza in Midtown. Here we met a local geotechnical engineer during his lunch break. We found it interesting to hear how incredibly expensive it is to try to raise a family there in Manhattan. He said it was fine living in a tiny box in a fun neighborhood before becoming a parent. Now that their child is a toddler, they needed more space, therefore he and his wife, also an engineer, need to move out of New York.
We finished our lunch just in time to arrive at the matinee showing of the Broadway musical Buena Vista Social Club. This was a fantastic performance telling the story of musicians during the time of the Cuban Revolution and then later, in the 90’s when they reunited for an album and tour. The music performance was spectacular as well as the choreography of the dancers. We all enjoyed the show very much. On the way back to the train station we stopped for a rooftop cocktail, then ate an incredible dinner of Dim Sum back in Port Washington. It was dark by the time we returned home and were greeted by Baxter who appeared to have managed the 13-hour separation from us just fine.

Next Week
The last day in Port Washington was spent provisioning and other miscellaneous chores in advance of our final moments in Long Island Sound. Current plans are to head to Manhattan by our boat, then turn south to Sandy Hook where we will stage for an overnight trip down to the Delaware River as we work our way back to Annapolis.
Our most recent video highlights our stay on Block Island.
Post # 25-36
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