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Oh wow, this is actually happening, huh? – Early September 2026

“For his voyage was made in the right direction; not speeding away from his spiritual self, but moving inward – while traveling with the winds.” 

– Walter Magnus Teller, from the introduction to Joshua Slocum’s “Sailing Alone Around the World”

To view all photos from this phase of the trip, see the Google Photo Album Here


September quietly arrived while I was enjoying the beauty of Boston Harbor, and in a way it took me a bit by surprise. As the end of the passage to Boston arrived, and I spent a few days hanging out with friends, the end of the week approaching felt like it must be about time to wrap up a week of sailing – a thing I’ve done nearly every summer for the last 4 years. To have the repeated realization that the trip will continue was something both quiet and yet very profound.

I started the month with a trip ashore to drop some laundry off. Always nice to start with clean clothes. I dropped my gear off with a wash and fold place as it was worth the extra cost to not be tied to a machine for a couple hours, and then made a long round of the harbor and hit the Aquarium, a visit we made when I was here as a kid. 

The New England aquarium is, I think, the best of its size that I have visited. The central tank is always breathtaking and the peripheral tank exhibits are varied and delightful. I checked with the staff and the display information, and confirmed that at least three of the residents and I had been there before, as Myrtle the main tank turtle, and Amelia and Trumpet in the seal tank were there in 1986. (I have always loved seals, as Selkie’s name might suggest, and it’s always joyful to watch them just fully occupy the water in bliss.)

Amusingly, from my mooring in the harbor I kept wondering what mechanical process it was that sounded like a sea lion barking… only to remember that… there are sea lions at the aquarium. RIGHT THERE. Barking.

I met my friend Megan for dinner and catching up, and then back to the boat for a solid, if slightly tipsy, night’s sleep. (If you’re a martini fan, the Smith and Wollensky at Atlantic wharf makes a KILLER martini)

The next two days I had the pleasure of my partner Ann’s company and we largely decided to just chill at the boat and catch up, as we’d not spent much time together in a while, and the rain set in – making a cozy if humid setting for reading and hanging out. Then made another day ashore and visited the USS Constitution for the literal other end of the sailing vessel reality.

Finished with people catching up, I took the opportunity to get in one last SCA event, at the local group’s fall blowout “Falling Leaves” which was a really nice chance to give some hugs before I’m away for a time. (I also made the final 6 of our rapier tournament, and won a period sword book I don’t own and had wanted)

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Last night under the lights of Boston

Then, it was time for the passage to NYC. 

I’d looked over the essential path, and figured that I needed at least 4 days to make the trip running solo. The plan, in general, was to make the leg from Boston to Plymouth, then Plymouth to Newport RI via the cape cod canal. From Newport I could make my way to somewhere in the middle of Long Island, and then the last push to City Island in The Bronx.

Reality, naturally, disagreed.

The seas in cape cod bay were pretty steep, but the sailing was good, and the winds were going to make Plymouth bay pretty rolly for the night, so I pressed on toward the canal, hoping to stop for the night in Sandwich at the marina there. I got to Sandwich and entered the canal at the right time to take the southwest flowing current, but despite pulling in to the marina, there was no room and they wouldn’t let me stay at the fuel dock overnight.  So… I ended up needing to run the Cape Cod Canal at night, solo. 

Daunting.

BoatNote: The man-made Cape Cod Canal has a tidal difference on the west (Buzzard’s bay) and east (Boston) side that means the water flows into and out of the canal as the tides come and go. This difference and the tidal movement creates a current as the water flows in and out, which will flow different directions depending on the tide state, and can be up to 6 knots at times – aka the general max speed of my boat. The canal rules govern how you can transit it, and one of them requires you to be able to do it in a certain time frame, and the only way for a boat my size and speed to manage that is to go with the current and ride it the right way, so timing is everything.

Despite the elevated pulse and blood pressure, the canal was fine. The shores are largely a long park and have streetlights, making a nice visual path, I had my new AIS system installed that helped keep me aware of boats coming my way, and the current gave me speeds up to 10 knots at times, so it was a quick trip. I rounded the peninsula on the west end, and made anchor in Phinney’s harbor out of the prevailing westerly wind for a much needed night of rest.

My next stop was Point Judith in RI, a large open harbor but a good night’s rest, and then pushing onward into Long Island sound, where I had one set of plans of where to anchor, but Niantic CT was where I wound up just due to seas and wind. That made it the 8th of September, and my mooring in NY started the 11th, so I had 2 nights ahead of me, and some big winds coming the following night from the East. Looking over my options, I made for Port Jefferson Long Island, a tight and well-protected harbor on the west side of the island, and nicely out of the big winds. Booked a night with the Port Jefferson Yacht Club (lovely folks) and stayed snug and sound while gale force winds swept in from the Atlantic.

My second night, for money and recording reasons, I spent out at anchor in the outer end of the harbor in some of the most beautiful scenery I’ve encountered in a while. Shore birds on the sand dunes a hundred yards away, and still and silent morning. I was sad to leave it behind, but I have plans in the city!

City Island is the most unique place I’ve ever visited in NYC. At the elbow of The Bronx, out past Pelham Bay Park, it truly feels like a Cape Cod village in New York. Highly multicultural, plenty of pizza, NY Metro busses…. And nautical bric-a-brack everywhere and one Main Street that little avenues branch off of, nearly all of them dead-end. Fascinating. I enjoyed their showers, and had some things shipped there I thought about needing while I was out on passage, and used them as a base to go in to the city – a 3 hour round trip from the dock.

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City Island is… where???

While in NYC I had the opportunity to swing by Simon and Schuster and meet one of the producers I’ve only worked with digitally, so we could do corrections for a book I recorded in my Maine studio back in August. A lovely morning, and quickly done, and I took the afternoon to go to the Statue of Liberty and Ellis Island.

We had climbed the statue in 86, and I got the chance to climb to the crown and recreate a photo my dad and I took. I’m sorry he couldn’t be here to do that with me again – miss you, dad. 

A fun bonus of the day was that my coin-and-return locker at the base of the monument had a coin in it when I got there, and it wasn’t a quarter! So now I have a Moroccan 1 dirham coin as a fun souvenir of the trip.

A horrifying moment was witnessing how horridly the spotted lantern fly has invaded NY, as the base of the monument had hundreds of them crawling all over. I squashed at least 30 before catching my ferry to Ellis island and steeping myself in the general history.

The end of a long day of work and adventure and travel found me back at my floating home, and ready to begin the second half of September… next time!


Comments

3 responses to “Oh wow, this is actually happening, huh? – Early September 2026”

  1. Sara Tremblay Avatar
    Sara Tremblay

    So proud of your true sense of adventure and ability to make this vision a reality! ❤️

  2. Steve Booth. S/V Gandalf Avatar
    Steve Booth. S/V Gandalf

    Thanks for allowing us to enjoy this trip again vicariously. When I sailed south the second time I did so much more offshore so I am enjoying your stops and time in the Chesapeake. Be safe. Enjoy!

  3. Jennifer Morris Avatar
    Jennifer Morris

    I, your mother, took the photo of you and your father at the top of Liberty’s crown. In 1986 I had only an inexpensive camera that took a roll of expensive film. Of course, selfies weren’t a thing, and digital cameras something beyond my imagination. Computers came into our lives many years later. Your Dad never cared to take photos, but I’ve always loved photography so I snapped pics as often as possible.

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