We Sailed to NYC and Then I Devoted Myself More Fully to Life on the Water
⛵︎ Logbook 8/17/25: 61 days into our global sailboat odyssey
Ahoy fellow explorers,
As we approached land from the Atlantic after days at sea, the skyline of Manhattan appeared through the haze like a human-built mountain range. We then embraced a different type of exploration.
On Friday, Corey and I traversed the vast, dynamic city on foot.
After living so long now aboard Chérie, at the whims of water & wind, it was refreshingly easy to plan and execute every aspect of the day. Google Maps said it was a 17-minute jaunt to a restaurant, and it was true. A walking tour started at 12pm on the dot. The weather forecast said sunny & 82 degrees and we could reliably enjoy the rays in a park.
The moment I may remember most, however, is my chat with a handsome young bookstore clerk where I purchased a copy of Moby Dick. He had the same edition on his nightstand and it was his goal to read it this year. I told him that I was already hooked after connecting tightly with the first two sentences:
“Call me Ishmael. Some years ago—never mind how long precisely—having little or no money in my purse, and nothing particular to interest me on shore, I thought I would sail about a little and see the watery part of the world.”
I told him about our sailing adventure from North Carolina to NYC and our aspirations to do a circumnavigation. He found it so fascinating and had a list of questions.
But I was sitting there thinking about what it might’ve been like switching places with him.
He lives and works in an infinitely fascinating city. Unlike the narrator in Moby Dick, there was much of particular interest to me on shore. Brilliant architecture, manicured gardens, world-class restaurants, trendy coffee shops, smart & inquisitive people like him. My choice to live on the water hadn’t faced so much contrast for months.
When Corey and I got back to the sailboat, though, I decided that I preferred my new fluid & breezy life. If I was living in Manhattan, I wouldn’t need to worry as much about Hurricane Erin. But I also wouldn’t feel the unrivaled delight of pushing through the unknown on the daily. It’s challenging to plan & execute, but that’s also what makes it an adventure in every sense. It’s much different than walking around a planned city, even one as sprawling as NYC. I’m completely in the moment when I’m sailing and I love it.
I then thought I’d continue to see the watery part of the world.
This week’s Logbook is about being totally committed. It’s the tale of our first open-ocean sail. On our 3-day journey to the Big Apple, one of us needed to stay at the helm at all times. We needed to track the weather and adapt. But we also got to keep experiencing growth & beauty unlike anything I’ve ever encountered on shore. It contains tons of high-resolution photos. And it talks about where we’re headed next.
Thanks for reading Radical Paths! The Logbook is a weekly invitation to follow our latest happenings during our global sailing odyssey. This week’s Logbook is available to ALL subscribers of Radical Paths!
If you become a paying subscriber, you can check out last week’s Logbook in its entirety, which is about the anticipation about our trip to NYC:
Also, this week I published a brief update on the last couple days in Atlantic Highlands, New Jersey, as well as an essay I wrote on our open-ocean voyage:
In the coming months, in addition to the Logbook, I’ll continue sharing more reflections on living a life with different goals than the majority, articles that will be useful to achieve your own “crazy” dreams big & small, and more.
As always:
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NOW:
Here is this week’s Logbook:
Miles from any city — our first ocean voyage: We prepared, planned, and then left Cape May. We spent 3 days at sea and it was a thrilling & beautiful roller coaster — particularly as we approached the NYC skyline.
Exploring NYC like the sailors we are: We spent a day in Manhattan sporting our scruffs, eating excellent food, and basting in the joy of having sailed there from North Carolina. Then, we planned what comes next.
1. Miles from any city — our first ocean voyage
We woke up on Sunday anchored in Cape May, New Jersey, and the weather forecasts still weren’t perfect. If we left then, the weather models said we’d spend 60% of our multi-day trip in winds under 8 knots. That would mean we’d barely make northern progress. We considered waiting another day for the winds to pick up. But it was safe to leave, and we were ready to go. So, we set sail and prayed to whatever Greek or Roman gods were in charge of delivering us some good winds. At least we’d be out on the water.
We motored out of Cape May Harbor fighting a slight current and wakes from the much faster vessels going out on that sunny Sunday. We felt like a little turtle trying to keep up with the speed boats and jet skis. But we were beaming. Once we got through the channel markers, we kept heading east for 5 miles, straight away from land, away from all those machines, before hanging a left and then pointing north.
We raised our sails, turned off the engine, and Chérie started flying. And that was the first time we ever sailed in the open ocean.
We had been anticipating this moment for nearly 2 months. Having only sailed in the protected waters of bays, harbors, rivers, and channels, we honestly didn’t know what to expect. Would the winds feel different out there? What about the waves & currents? Would it feel eerie seeing the coast fade away in the distance as we got further away from shore?
We’d learn all these answers in the coming days.
Immediately, we discovered that the wind gods had delivered. They were stronger than forecasted. We saw steady winds at 10 to 12 knots out of the southeast, which was a dream for Chérie. That meant we were sailing north at 4 to 4.5 knots — a respectable speed for our little adventure pod.
The waves pulsed differently out there than we had ever seen before. The water moved like it was from the breath of a much larger beast than the ones we knew in the bays & rivers. But Chérie handled it as beautifully as all the rest.
As we saw the coast get smaller in the distance, I saw nothing creepy about it. It was humbling, yes. I knew that we were at the mercy of Chérie being able to keep us afloat. But I believed in her. She had not only been my home, but she had been my protector 24/7 for nearly 2 months. We had been through a lot already, and she hadn’t ever shown signs of wavering. I knew that nothing was promised going forward, but the worst case scenarios were the furthest from my mind. I was 100% in the moment and loving every bump of the sea or roar of the wind.
It ended up being a pretty normal day on the water, just as the day-long sails we’d experienced for weeks in the Chesapeake Bay. We took shifts steering. We peered off into the horizon. I went down to check on our cat, Pineapple, only to see her sound asleep on a cushion, just as always. And I started making beans & rice with colorful veggies for dinner.
The big difference came with sunset.
Not only did it hit different on the open seas, but this time we wouldn’t be pulling into an anchorage.
We’d keep sailing.
Every sailing crew manages their night shifts a bit differently, and given we’d never done it before, we guessed on an arrangement that we thought might work. Corey would do the first 1-hour shift at the tiller while I slept, then we’d switch, and so on, all through the night.
But that sucked.
The first couple times we switched off, it was a novelty waking up with barely any sleep in the bank. But then we became more like zombies than sailors. Thankfully the winds were lackluster. They had finally died down to about what the weather models had predicted. We saw 2 or 3 knots at times, which was barely enough to fill Chérie’s sails.
At many points that night, it died down to nothing and then would pulse back. Chérie’s sails would sag, then the wind would come back and fill the sails completely and make a disturbing sound, like they were being overstretched and could burst open.
We let it go on for a bit, thinking we had no choice, but while I was sleeping Corey got concerned that it was too much stress on the sails. He tried to wake me up down below. He yelled for me, but I was fully zonked. He came down below and shook me and I didn’t budge. Finally, I woke up while he was in the cockpit and he was frustrated. I was mad at myself that I couldn’t wake up.
“What happened?”
Our sailboat was at a complete stop.
Corey halted the boat using a method called “heaving to,” which is when you arrange the sails and rudder so the boat steers into itself and remains parked on the water. We weren’t moving, but the winds had been so light anyway that it didn’t matter. It had stopped the pulsing of the sails, too. So, we would stay parked until the winds came back and then we’d continue taking our sweet time north up the Atlantic Ocean.
After we both drank coffee, we shook off our trances and geared up for what would end up being the best sailing day of our lives.
The winds had returned.
The wind was steady at 14 knots and we were soaring through the water.
We celebrated our 17 year anniversary that day. At one point weeks earlier, we hoped we’d be exploring Manhattan already, but that sort of timing doesn’t work out when you’re a sailor. We plan the best we can, but we write any specifics in sand with a stick at low tide. You just roll with it and that’s part of the joy. I still had some plans for a great dinner, which was our greatest guilty pleasure on the boat: shepherds pie filled with mashed potatoes, green beans, carrots, BBQ sauce, and spam (yes, spam). And before you judge, just trust. It’s perfection.
But I didn’t know we’d be eating the meal with some food in our bellies already.
We had decided to throw the trolling lines in the water and try to catch some fish. I had my hook in the water for about 40 mins dragging behind Chérie, and I didn’t get a bite. Then, Corey threw out another hook using a fishing pole we brought with us from North Carolina. He’s not the most patient fisherman. Within 5 mins, he said, “I haven’t even got a nibble.” And literally right after he completed that sentence, he caught a fish!
In the excitement of the moment, we didn’t do the ceremonial picture with Corey holding up his catch. We also didn’t have internet. We didn’t know what kind of fish it was, how to fillet it, or how best to cook it. We settled on a filleting method that left some bones in there (not a good one), and I cooked it way too long (it tasted more like chicken thigh than a fresh-caught fish). But it was the best anniversary snack imaginable.
Later, I asked Corey to reflect on the last 17 years of our relationship. We had been together so long, and had so many chapters together, it was a long discussion.
We had grown up together. We rode bikes to class in Portland in our 20s. We backpacked through India and Asia. We built careers in Boston. We made a home in Denver. We refit a sailboat in coastal North Carolina and began an epic sailing adventure with basically no experience.
I asked him, “What is your favorite chapter?”
He was stumped. “This one? All of them?”
I also couldn’t answer the question.
How does one pick a favorite when there’s a collection of perfect moments to choose from?
This sailing voyage has taught us both that the book is not written. We’re still learning so much about each other and ourselves. And we’ll continue writing until the end of our days.
That next night, we decided to do 2 hour shifts and that worked way better than the night before. I set my alarm on the other side of the boat so I couldn’t turn it off in my sleep. I was fully alert at all points on my watch and loved every moment I spent in that cockpit alone. Thankfully, we had enough wind to engage the wind vane, which is a self-steering system we inherited with the boat that expertly uses the wind to steer. It was the definition of smooth sailing.
At sunrise, I saw shining dots in the sky that I swear were planets.
Then we made our final approach to NYC.
But the wind forecast had changed for the worse.
The weather models suddenly showed us entering NYC in 25 knot winds going against currents, which meant that there was a good chance of seeing huge waves. We hove-to because we would have to time the currents anyhow, but we were a bit stumped about what to do. The winds weren’t predicted to die down until much later in the evening, and so if we didn’t go for it then, we’d likely stay parked all night in the huge gusts and swells. We had sailed in 20 knot winds before, and we felt confident that we could do 25. But we needed to pick the least-bad option.
We decided to go for it.
The final leg on our journey was the roughest we’d ever experienced, but it was also extremely rewarding once we made it through. We saw the high winds as predicted and waves reaching at least 6 feet that hit the back corner of Chérie in quick succession. We got sprayed with water. I went below deck at one point to put away my nice camera and check on Pineapple, and I learned the hard way that I needed to be holding onto something at all times. A wave hit us and my knee bashed into a galley cabinet. We both stayed on deck and Corey steered us through the high winds and waves. We attached our harnesses to the cockpit so we wouldn’t fly off the boat.
We were committed and there was no going back.
We made it through unscathed.
We then motored to a calm anchorage in Atlantic Highlands, New Jersey, which would be just a short ferry ride to NYC.
And by the way, Pineapple was fine.
2. Exploring NYC like the sailors we are
It was a long 3 hours on that rocky & rolly leg approaching NYC, but we finally made it to the protected waters in Sandy Hook Bay. This is a common anchorage for folks making this trip because you can’t exactly stop right next to the skyscrapers in Manhattan. It was only a 45-minute ferry ride from Atlantic Highlands to the city.
That one day traversing the city on foot will be it for us.
However, on our way further north, we’ll sail passed the Statue of Liberty, up the East River, and pass Manhattan on the east side. We’ll head under the Brooklyn, Manhattan, and Williamsburg bridges. Then, we’ll swing around Long Island and out of the city. Stay tuned for next week’s Logbook for the details (and pics) from that voyage!
As much as I love aspects of city life, I realize now that I really love life in general — no matter where it is. There is something to enjoy about any permutation we choose, city or sea. The most significant parts from our recent days were when we were pushing into the unknown, trying new things, and seeing how life could keep surprising us.
I’ll remember the handsome man from the bookstore perhaps the most, and I’ll wonder what he thinks about Moby Dick as I study it over the next couple months. I’ll ponder if he’s thinking about my journey as much as I’m thinking about his. But I know that one isn’t better than the other — as long as we’re both finding aspects that fulfill us.
As sailors, we now set our sights on the next place we can reach from the water. We’re now making plans to leave Atlantic Highlands on Monday, but it depends on what Hurricane Erin kicks up around here before she heads out further to the Atlantic. We could get stuck here a bit longer waiting for a weather window.
Our goal is to head up to Newport, Rhode Island. This is a famous sailing town, which we used to visit by land when we lived in Boston. Like NYC, it’ll be a new perspective on a place that fascinates us and we know has a vibrancy we’ll also soon be saying good-bye to.
I can’t wait for that perspective, too.
Even though I find much to love in all these places we visit, including the fascinating people, we’re fully committed to this chapter seeing the watery part of the world. We can’t experience all the joys of living & working in Manhattan right now. Maybe someday in the future. But right now we’re fully immersed in the moment here in our floating home and we’re loving it. And when we remember that we affirmatively chose this life, it makes us more excited for whatever the future holds.
Until next time,
—Cory Vinny
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I wish you guys stayed longer in NYC! Would have loved to meet in-person! Also, so cool to read that you sailed under the Brooklyn, Manhattan, and Williamsburg bridges! Good luck with the rest of the trip! :)
Cheers to thrilling adventures and big anniversaries! My partner and I also recently celebrated 17 years together and 15 years married. Glad you two are still crazy kids at heart 🤪