Just Don’t Be Late
Simple Life was supposed to leave the dock on Saturday, October 17th. Now, two weeks later, it’s Halloween and Preppy and I are out on the bow in the blowing snow trying to wire up a windlass.

It’s Cold!
Our hands are barely working after letting go of the freezing cold anchor chain. We laugh at how ridiculous the situation is.
It’s says it’s 34 degrees and snowing but the raw wind definitely does make it feel like 22 degrees.

Snow! It’s everywhere.



The original departure date was missed but with Preppy aboard we were now ready to depart. Another quick check of the weather and there’s the remnants of a hurricane that are blanketing our area.

Gale Warning
So we give it a couple days and what’s next? A Gale Warning!


The Shanty
With nothing to do but wait we decide to walk to The Shanty for dinner and some IPAs .

Frozen Dock Lines
It’s Halloween morning and Preppy is going home as he has next week’s jobs to prepare for. Preppy had agreed to make the trip over to the fuel dock in the morning before we parted ways. The only challenge now was getting off the dock?
Sometimes I don’t think… I just do. So when Preppy said the dock lines are frozen solid on the cleat, I just grabbed the torch which was right next to me and started heating them up. It was not until Preppy said … Umm.. why don’t we just pour some hot water over them? Duh? Yes, that did the trick!
With the dock lines finally freed we made our way out of the slip and over to the fuel dock.

At the fuel dock were Peter & Leslie of MV Leap of Faith. They were attempting to use the pumpout hose but it was frozen and would not operate. MV Leap of Faith is also heading south for the winter. They travel faster than I do so we’ll stay in touch as we go through text & calls.
I really like leaving with full water tanks and an empty blackwater tank, especially when it’s cold as I’ve run into situations where you try to pull into a marina to get water & pumpout and it’s either frozen or winterized. I spent quite a while with the pumpout hose locked open and in the seawater till it thawed and came to life writhing like a snake. A short suck of the 54 degree seawater and it was time to pump out.

The Lookback
As I pulled away from the fuel dock, I looked back. Every time I leave I look back. There is an undeniable feeling of freedom. It’s the first moments of a 6 month, 5K mile journey. I smile. The world seems right.

As I pass Warwick Neck I can see the snow covered Warwick Country Club.

Point Judith
MV Leap of Faith had already called me and gave me the word that the sea was very calm when they exited Narragansett Bay. I was passing Point Judith Light and slowing coming up on a Hunter sailboat who was also enjoying the trip west down Long Island Sound.


At this moment I noticed that my Garmin satellite tracker seemed frozen. I checked my blog’s current position page and it showed that I was still in Warwick, RI? I quick reset of the satellite tracker and it update my position. Ofcourse it drew a straight line between where I left and where I was when the tracker came back to life. I’m guessing someone is going to ask me how I piloted the boat over the state of RI?

Watch Hill
Soon I was passing Watch Hill, RI and some of the beautiful homes along the coast.


Fisher’s Island
I made my way up the inside of Fisher’s Island. There were fishermen working the current between the island and mainland CT.

I don’t know a lot about Fisher’s Island but it looks beautiful as you cruise past.



On the west side of Fisher’s Island you must keep an eye out for the ferry’s as they can sneak up on you pretty fast.

I had planned to anchor behind Fisher’s Island because I had never done that. However, the sea was calm and the moon was bright. I decided to keep going west. The area around Fisher’s Island is called “The Race” and it has strong currents and often gets pretty choppy. Getting inside the northern fork of Long Island seemed like the right thing to do.
With the sun setting Long Island Sound looked amazing.



As night settled in around me I flicked my running lights on and settled back in the captain’s chair for a long night.

Ultimately I settled on an anchorage with only minimal protection but “just off the beaten path” as they say. Not to far inland that it takes an hour to get in and an hour the next morning just to get out.
I anchored just off Fort Trumbull Beach in Milford Harbor. This location is just west of Bridgeport, CT. There is a small island called, Charles Island with a low-tide land bridge. You need to watch your tides down here near the head of Long Island Sound. If you anchor at high tide you might wake up at low tide with the boat resting on the bottom.


The time was now midnight. It had left Warwick, RI at around 10AM so roughly 14 hours to Bridgeport, CT. The 1st 98NM leg of my Winter 2020 journey looked something like this.

It was around 1AM by the time I took a hot shower and got to bed. I’m typing this blog post as I sit in the captain’s chair navigating leg 2 of my journey. Stay tuned for the Leg 2 post.

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