Passages South (Long Island Sound and New York Harbor)New London, CT to New York.

Passages South (Long Island Sound and New York Harbor)

New London, CT to New York, NY

The Statue of Liberty stands majestically against the New York City skyline, viewed from the waters of New York Harbor.

Our cruising plans started one winter day 8 months before our departure. We wanted to escape the cold winter of Connecticut, show our daughter that there is more to life than the hustle and bustle of New England living and work created an atmosphere for the previous 10 years that required a break; even for the most strong willed. The plan was to sail for just for a year, head to the Bahamas for a season and come back to some sort of land based life after we returned; little did we know at the time 2 years later we are making plans to stay as long as we were happy doing it.

We left our home port just north of long island sound in mid September of 2023 on a foggy morning bound west to New York, NY. As we called back to the bridge  “thanks for the opening and see ya next year” there was a moment of joy, bittersweetness and anxiety of the unknown. We had done weekends aboard, week long trips and a delivery of our boat from Vermont to Connecticut but this was different. Our daughter Sophia was excited as ever, its funny how kids adapt to new things so easily and this new lifestyle was no different. We made our way past ledge light and out of the mouth of the Thames River; shortly after turning west down long island sound an hour or so into our sail a strong front coming from the northwest came right over the top of us. We watched another sailboat fly past us in the same direction, heave to, wait for the front to pass and then continued on about their journey. I still admire that boat and it think of that moment to this day, so confident the captain as they precisely executed their maneuvered then continued on their journey like nothing ever happened. We took a much different approach of beating into the weather like we were driving a car as rain drove sideways into the cockpit. With the girls downstairs everyone listened to the thunder rumble through the sound as the boat steered under autopilot toward Branford, CT.

Our first stop of the trip would be Thimble Islands which is a small group of islands on the Northern side of the sound named this way because the islands look like small thimbles sticking out of the water. Its beautiful and can remind you of the Maine coastline. We “dropped” the anchor based on the conditions, lowered the dinghy and headed to town to walk the dog. After a brief  walk, a failed attempt to get an ice cream and a dinghy ride back to the boat we settled in for the night. Sophia fished off the forward deck and we sat and enjoyed the view of the sunset and waited for nightfall. Over the years we have used a couple different options for anchor alarms and I have learned a lot from past mistakes made in setting them right now we use anchor pro which seems to work the best of us we set it and now keep the app open on a phone upside-down so the light doesn’t affect us sleeping in our cabin this way it actually alarms when there is a potential issue. As the sun set we turned in for the night, suddenly at 3 A.M. we were startled out of bed. We arose to find the boat dragging in 20-25 knots with the wind coming from the opposite direction than where is was when we turned in, clearly I didn’t recognize the change at this stage in our cruising life. Of course we immediately started the engine with Anna at the helm we safely motored forward and out of the danger of the rocks. A total of a 1/4 mile we dragged from our initial position into the channel and on our way out into the sound. We narrowly escaped rocks, avoided the lobster pots and even missed a moored boat by feet as we frantically worked on raising the anchor and getting the boat back to safety. As I do during the events that create havoc I thought about what could we have possibly done wrong, we skipped a step that our instructor taught us long ago on a previous boat, to back down at a minimum of 2000 RPM. Why? Who knows maybe it was the first night jitters, extra confidence from actually slipping the lines and leaving or maybe it was lack of thought of what needed to be done I think eventually it happens to everyone. Either way the dream could have ended on the first night out but Bogumila had other plans and was looking out for her crew in more ways than one. In the remaining darkness of the night I sat in the cockpit after resetting the anchor and watched the water boil as the sunrise brought in schools of striped bass and bluefish. A quick walk with the dog on shore, breakfast to refuel for the day and a brush off of our egos we picked up the anchor and put an end to our first anchorage with a few new lessons learned.

As we left the Thimble Islands another sailing family who also departed New London, CT passed by us in route to the Bahamas as well. We said quick hello and later created many memories together. They turned in to harbor just after passing by New Haven but we had plans of making it to Norwalk, CT to find a place to hide while Hurricane Lee passed by us. The forecast wasn’t clear at the time for what the storm was going to do but we picked Norwalk because of its all around protection from the sound and availability of moorings and marinas. Having made no reservations prior to our arrival we called a few places and quickly realized that there wasn’t much available unless we went way up the river fortunately we lucked out and found the municipal mooring field, checked in and secured the boat for the night. After the previous nights adventures we were happy to be secured to something we were more familiar with and knew wouldn’t move while we slept. Norwalk is a fairly nice town but its more closely related to a NYC’s suburb than a quaint Connecticut town you think of when you see a Yankee Magazine but it had enough to keep us busy while we were there. We happily visited the Norwalk Aquarium, the local mall, local grocers and a few  restaurants during our 4 day stay. There is reasonable access to the boat ramp to walk the dog if you have one and I can recommend the moorings if they are available when your in town but the marinas are expensive given their location.

After hurricane Lee passed by to the east making more of a presence on the eastern New England shoreline than in Norwalk it was finally time to leave. A quick stop for fuel and of course I dropped the fuel cap into the water and had to replace it in the local ships store, add a rationing chain to the list of things to do. We were on our way to Port Washington, NY on the south long island sound shoreline.

Port Washington, NY for those of you who may have not visited yet is probably one of the most convenient stops in all of the eastern seaboard from our experience. Things that we consider convenient to cruisers are ease of access to land, access to necessities like grocery stores, chandleries and basic needs and access to local attractions for things to keep our the crew occupied. There is 2 public dinghy docks along with several marinas and yacht clubs as well as a public park within the anchorage, the grocery store is across the street from the North dinghy dock and is no more than a few hundred foot walk, the west marine is a 1/4 mile north from the dock location, serval very good restaurants exist within walking distance. One of the best parts of this anchorage is that there is access to the LIIR railroad station no more than a mile away from the dinghy dock. This train goes directly into NYC’s Penn station and takes about 45 minutes to get there. This gives you access to the entire city VIA public transportation at a fraction of the price of staying in Brooklyn or on the NJ side of the Hudson River. If you have never been to NYC and you enjoy visiting cities you have a  plethora of options to see and do from this harbor.

The second best part about port Washington is for the weary sailor. Those that find there way here northbound and you are lucky enough to catch and open mooring you have access to the town VIA water taxi as of 2025 the moorings are no longer free on the first night which was one of the best deals around but at $35/ngt with launch service there is nothing better than resting on a mooring after a long sail. Points south are a long stretch here from Cape May/ Lewes, the Delaware Bay, Norfolk or points south its a welcoming sight to tie up to a mooring to get some good needed rest. Southbound yachts can stop here to make the best timing of the East River and the infamous Hells Gate. You can certainly not go wrong with stopping here in either direction.

After a few days in Port Washington it was time to leave. From here transiting the east river is an breeze from the harbor its maybe 2 hours or so to the gate which makes timing this run very easy. We had done hells gate a couple times in the past and there is a plethora of information online, in pilot guides and other resources to plan your trip in either direction. Its a great experience to see NYC from the water and a very exciting day that ends with a view of the statue of liberty going westbound. There is something that the world is enamored by with this landmark; it has beauty like no other and stands for something almost everyone can relate to. Every time we pass by here there is always several photo ops and no matter how many photos you have of lady liberty there’s just one more you can take. After our sail by we typically stop at the city marina just north of Ellis island on the Hudson River to top up with fuel for the next leg down the NJ shoreline. We quickly topped up our tank and headed to Atlantic highlands for a rest before the long stretch south along the NJ shore.