Our cruising plans started one winter day, 8 months before our actual departure. We wanted 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, 2 years later we are making plans to stay as long as we were happy cruising.

Casting off from home

We left our home port, just north of Long Island Sound, Connecticut, in mid September of 2023. It was a foggy morning, and we were bound west to New York.

As we called back to the bridge “Thanks for the opening and see ya next year” there was a moment of joy, bitter sweetness 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 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 think of that moment to this day, so confident the captain as they precisely executed their maneuver then continued on their journey like nothing ever happened. We took a much different approach; beating into the weather like we were driving a car down the highway 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.

First stop: Thimble Islands

Our first stop of the trip would be Thimble Islands, 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. It’s beautiful, and can remind you of the Maine coastline.

We dropped 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, waiting for nightfall.

Awaking to our first emergency

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 for us. We set the pin as soon as we drop the hook and now keep the app open on our phone upside-down in our cabin so the light doesn’t affect our sleep.

At 3 AM, we were suddenly startled out of bed. We arose to find the boat dragging in 20-25 knots with the wind flipped from the opposite direction to where it was when we turned in; clearly I didn’t recognize the forecasted change at this stage in our cruising life.

We immediately started the engine with Anna at the helm, and safely motored forward out of the danger of the rocks. SV Bogumila had dragged a 1/4 mile from our initial position; we were in the channel on our way out to 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 events that create havoc, I thought about what we could 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 a lack of thought about what needed to be done, and I think eventually it happens to everyone. Either way our dream could have ended on the first night out, but SV 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 confidence, we picked up the anchor and put an end to our first anchorage with a few new lessons learned.

Waiting out a hurricane in Norwalk

As we left the Thimble Islands, another sailing family who also departed New London passed by en-route to the Bahamas as well. We said a quick hello, and later created many memories together. They turned into harbor just after passing by New Haven, but we had plans of making it to Norwalk to find a place to hide while Hurricane Lee passed by.

The forecast for what the storm was going to do wasn’t clear at the time, but we picked Norwalk because of its protection from the Sound, and the availability of moorings and marinas. Having made no reservations prior to our arrival, we called a few places and quickly realized 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 night’s 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 is more closely related to a NYC suburb than the quaint Connecticut town you think of when you see a Yankee Magazine. That said, it had enough to keep us busy while we were there. We happily visited the Norwalk Aquarium, the local mall, grocers and a few restaurants during our four 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 you’re in town.

Southbound to Port Washington

After the hurricane passed by to the east, it was finally time to leave. A quick stop for fuel (of course I dropped the fuel cap into the water) we were on our way to Port Washington, on the southern Long Island Sound shoreline.

Port Washington, for those of you who may have not visited yet, is probably one of the most convenient stops in all of the Eastern Seaboard. It has two public dinghy docks along with several marinas and yacht clubs, a public park within the anchorage, a grocery store across the street from the east dinghy dock, West Marine is a 1/4 mile north from the dock location, and there are several very good restaurants within walking distance.

One of the best parts of this anchorage was the access to the LIIR railroad station, no more than a mile away from the dinghy dock. This train goes directly to Penn Station in New York City, taking about 45 minutes to get there. That gives you access to the entire city via public transportation at a fraction of the price of staying in Brooklyn or on the New Jersey side of the Hudson River. If you’ve never been to NYC and enjoy visiting cities, you have a plethora of options from this harbor.

The second best part about Port Washington makes it perfect for the weary sailor; those who are lucky enough to catch an open mooring, have access to the town via a free water taxi. Unfortunately as of 2025 the moorings are no longer free on the first night, which was the most welcoming part, but at $35/night with launch service it can be an appealing place to rest after a long sail. The last ports are a longer sail from Port Washington for northbound yachts, so it can be a welcoming sight to tie up to a mooring. Southbound yachts can also stop here to make the best timing of the East River and infamous Hell’s Gate. You certainly can not go wrong with stopping at Port Washington while going in either direction, and we highly recommend it to anyone transiting this area.

Through the East River and past Lady Liberty

After a few days in Port Washington it was time to leave. From here, transiting the East River is an breeze. It takes 2 hours or so to to get from the harbor to Hell’s Gate, making timing this run very easy. We had done Hell’s Gate a couple times in the past, and there is a plethora of information online, in pilot guides and other resources to help plan your trip in either direction, as you must be aware of the tide and strong, swirling currents.

Navigation aside, it is a truly great experience to see New York City from the water, a very exciting day that ends with a view of the Statue of Liberty.

There is something that enamors us 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. There are also places to anchor right next to Liberty Island, if you’d like to linger.

After this sail by we typically stop at the marina just north of Ellis Island on the Hudson River, to top up with fuel for the next leg down the New Jersey shoreline. We quickly topped up our tank and headed to Atlantic Highlands for a rest, before facing the long stretch south along the New Jersey shore.