Sailing in Rags & Scruff, I Realized I’m Living My Fantasy

⛵︎ Logbook 8/3/25: 47 days into our global sailboat odyssey

Aug 03, 2025

Yesterday, we sailed under the Chesapeake Bay Bridge on our multi-day journey from Annapolis to New York City

Ahoy fellow explorers,

I’ve become so passionate about my obscure living arrangement that I forget some people could possibly be aghast by the details — especially my friends.

But last week, when I told a friend that, yes, he could spend the night with us in Annapolis, I then wondered: will he be OK peeing in a jug?

I told him about our limited sewage capacity, and while I was at it, I added some other details to set his expectations.

Aboard Chérie, we have few amenities. It’s a very small space. And not everything works as it should. For example, we need to strain our freshwater through a coffee filter to catch debris from our water tank.

“It’s sorta like camping,” I texted him.

He didn’t sound so enthralled.

When he asked about the onshore bathroom options instead, which would require a 5-minute dinghy ride and 10-minute walk, I realized maybe he should get a hotel.

Some of the people closest to me would absolutely see the magic and coziness aboard Chérie, including all the work Corey (my husband) and I did to get her operable, the wood paneling below deck, hand-sewn cushions, and snug beds where you can’t quite stretch out your legs.

But it’s definitely not for everyone.

And that may be what makes me love it most.

This week’s Logbook is about how not everyone who loves the idea of staying the night on a sailboat will understand my particular sensibilities. It’s about how even when you’re part of a big loving community, you’re still going to have your own quirks that differ drastically from the crowd. And sometimes it can make a person (like me) wonder whether they’re the crazy one. But then, we fall back in love with our own way of chugging through life.

Thanks for reading Radical Paths! The Logbook is a weekly invitation to follow our latest happenings on the water during our global sailing odyssey.

This week’s Logbook will be available to ALL subscribers of Radical Paths!

This week, I also published my first ever guide explaining how you too can take a radical path — but it’s about more than becoming a minimalist sailor. It’s a framework that I’ve applied >25 times to usher in new beginnings of all shapes & sizes according to my own metrics of success. I hope you check it out:

7 Steps to Begin & Master Your New Radical Path

Cory Vinny

Jul 31

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In the coming months, in addition to the Logbook, I’ll share more articles that will be useful to achieve your own “crazy” dreams big & small, detail inspiring stories about real-life adventurers, and publish more reflections on living a life with different goals than the majority.

Here’s how it works:

Paying subscribers: You’ll receive ALL my regular articles, all archived posts since the beginning, and a new Logbook every week. And you’ll receive boundless thanks from my floating family 😸⛵️
Free subscribers: You’ll get some regular articles and a new Logbook every other week.

I’d love to hear from all of you in the comments or through DM. Thanks for reading along!

If you become a paying subscriber, you can check out last week’s Logbook in its entirety:

Sailing at Night Was Like Aiming a Spaceship Toward a New Planet

Cory Vinny

Jul 25

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If you can’t swing a subscription, and you’d still like to get all the details about our voyage, you can DM me and I’ll make you an honorary paying subscriber.

But if you’re able and willing, I want to say thank you from the bottom of my heart. Your subscription will help us reach our “impossible” dreams, sustain our adventure, and keep sharing with you all for years to come.

NOW:

Here is this week’s Logbook:

Loving my scruff in Annapolis — even among more-polished sailors: It’s very rare to find other nomadic sailors quite like us in the vast “sailing community.” But that doesn’t mean I don’t love my choices.
On our next adventure to New York City: We’re finally ready to go to the ocean and introduce Pineapple to the Big Apple.

1. Loving my scruff in Annapolis — even among more-polished sailors

Entering Annapolis last week, Chérie merged with 1000s of sailboats to become a small part in what felt like a thriving marine ecosystem. Unlike in Solomons, which felt like it had a similar magnitude of ships but was rather disappointing in terms of seeing people sailing, Annapolis was teaming with sailors out and about. It was a Tuesday evening and yet the whole town seemed to be out in their sailboats. Endless ships scattered the harbor, all shapes & sizes, from the luxurious to the practical to the dilapidated.

We felt like we had arrived.

We paid for 1 week at the mooring in downtown, because we knew this sailing wonderland had supplies & services we couldn’t get anywhere else, and we’d find plenty to keep us busy in this beautiful old city.

For example, we hoped some folks in town could help us pry our metal vang apart before the boom holding up our mainsail crashed on our heads.

We figured we could also work on projects galore.

And maybe we’d meet some cool, similarly-aligned people in this vibrant sailing town who also peed in jugs.

It had been a couple sweaty weeks since we had a freshwater shower, and we had grown quite sticky & scruffy in the extreme heat and humidity.

I’m surprised how comfortable we’ve gotten together without certain luxuries, but it may just mean we’re still excellent life partners, even after nearly 17 years.

Even though I’m shocked sometimes at how I look like my dad when I see my scruff in a window, it’s a perfect reflection of who I am now:

I’m a sailor focused only on his adventure.

Once we got to shore in Annapolis, however, the other residents in this boating paradise were clearly not roughing it like us. It’s a well-polished old city, in some ways an affluent suburb of Washington, D.C. Many of the sailboats we saw when we entered the harbor were 5-20 times more expensive than Chérie. Also, the U.S. Naval Academy is right near where we parked our boat, which meant many of the folks around were some of the best-groomed people in the country.

Even fellow transients in Annapolis, weren’t roughing it like us. I doubt few of these sailors went without fridges or spared any running water to groom themselves.

I suddenly felt like I might as well have been walking around in rags.

And I started to question myself a bit.

The insecurity of not fitting in with the crowd — especially one that I considered to be mine, like fellow sailors — was a devastatingly familiar feeling. It reminded me of how I felt among the straight jocks in high school. The folks decades older than me in alcohol rehab. The botoxed gays of West Hollywood, California. My brilliant classmates at Harvard. My buttoned-up coworkers at my old career.

I have routinely felt like a cat that learns to live in a house full of pooches. The dogs were often admirable creatures, but the situation would cause me to second-guess my instincts doing my cat-like things. So, I’d try to adapt. But I never felt like I was enough.

In the past, I would just try my best to fit in.

But this isn’t what this chapter is about.

As a sailor, I’m living by my principles and I love my choices.

I still held hope that we’d meet fellow budget cruisers at some point soon. I knew there were other sailors living like us on a boat that only has the basics, and that they were loving their lives just as much as me and Corey.

Then, on our 4th day in Annapolis, we finally met a fellow sailing couple named Matt & Lizzy who had lived on their sailboat for more than 1 year. They were anchored for free further up the river and happily took the longer dinghy trip to town. I admired their thrift, as we were paying $25/night in the more centrally located moorings. We shared stories with Matt & Lizzy about our trip up from North Carolina. They told us their tips about living on the cheap and about the amazing anchorages down in Florida at a place called No Name Harbor.

They still thought we were crazy for not having a fridge on Chérie but it was followed by a heartfelt laugh.

Later that day, I’d see a beautiful, perfectly groomed sailboat family ride by us, and I’d briefly question myself again.

I wish I wasn’t so doubtful when I was suddenly faced with people who have different vibrations than me.

I wish I could tell you all that I was the sort of cat that kept chasing the laser pointer despite the dogs looking at him confused.

But my environment has an enormous effect on what I believe about myself.

My ecosystem gives me cues about what’s OK and what’s not.

My primal instincts are wired to feel scared when I realize I may be an outcast.

But the mesmerizing part about being in Annapolis was that feeling getting back to Chérie, where it was just Corey and I, and all my doubts evaporated.

This is the journey that I want.

I wasn’t lying when I said I was so passionate about this way of life.

I love my experimental curiosity and how I’m focused on testing these social norms I witnessed all around me my whole life — and witnessed all over in Annapolis — about what’s necessary and correct for us all.

I did shave and shower the first chance I got, but it was mostly for me. And for Corey, in case I smelled.

But almost immediately, I learned that I missed the scruff.

2. On our next adventure to New York City

We ended up spending more than a week at our mooring in Annapolis. It was sticky in more ways beyond just the humidity. The conveniences in town were addicting. We could get a massive and amazing Reuben sandwich for $12 to split. Homemade ice cream at 4 different spots. Brick-lined sidewalks that we’d walk just to enjoy the buildings and homes older than the country they stand in.

I also overcame the insecurities I felt those first days.

I realized that the words “sailing town” actually indicated a ton of diversity.

And I loved that.

We even found some experts separated our stuck vang for us — for free!

We hauled this vang with us from North Carolina, and in Annapolis we finally found someone to pry it loose (the two metal pieces were stuck together)!

Then, we were ready to leave but Mother Nature told us No.

One day of delays due to severe thunderstorms.

Another because of a weather warning for “small crafts” on the Chesapeake Bay, which we assumed included us, just north of Annapolis.

Then, we were ready to make our escape but it took a half day just to refill our diesel tanks and drinking water. Another night at the moorings!

But then, yesterday, we finally took off,

We headed north at 7am, sailed under the miles-long Chesapeake Bay Bridge, and are making the multi-day (week?) passage to New York City.

We sailed under the 4-mile-long bridge and felt like champs, especially because the other sailboats around us were motoring.

We made slow progress up the Bay in light winds, but it was still a glorious sailing day. We didn’t motor! But we felt great about our progress.

Getting to New York, it’s going to be the first time leaving the protection of bays, rivers, and canals, and finally sailing offshore. It’ll include at least one overnight sail on the ocean.

We’re both nervous, but we also know this is what we signed up for.

We’re here to push ourselves as sailors to walk through the fire that stands in our way and emerge as new people, totally transformed.

And we have our sights set much further than just New York.

We’re only planning to spend one day in Manhattan, mostly to get some Bleecker Street Pizza and bounce. We’re mostly excited for the novelty of having sailed there!

But as we’re walking the streets of Manhattan, I’m certain I’ll feel similar insecurities as I had in Annapolis — at least for a bit. All the beautiful fashion models, serious people in suits & ties, cool-looking artists, parents pushing strollers, and tired folks coming & going from their jobs — reminders of how I’ve chosen a much different path.

But doubting my decisions for a brief moment of a day is a beautiful opportunity in itself. Yes, I’ve made radical choices that differ from the norm in my country.

I could continue being the cat that gives up his cat-like instincts and tries to join the pack of pooches, hoping to “belong.”

I could become whatever “average” is in Annapolis or New York and search for bits of that normal life to enjoy.

But my decision to become a scruffy sailor was one born out of my principles. I jumped in to test out the water. And I organically adapted to this new environment.

I’m a sailor focused only on his adventure.

We met Matt & Lizzy and I now know there are 100s of other budget cruisers like them, like us, who will make me love being that crazy cat.

I’m learning that sailing can look different for all sorts of folks, too, but my embrace of the minimalist brand is all about seeing that there’s beauty hiding under these unturned rocks.

I’m totally uncertain about where it’ll take me or what I’ll learn about my personality and needs going forward.

And that’s the point.