We Finally Embarked On Our Huge Sailing Odyssey and I Already Thought My Husband Would Die

⛵︎ Logbook 6/20/25: 3 days since setting sail

Photo of our sailboat, Chérie, heading away from the boatyard in New Bern, NC, for the final time.

Ahoy dear readers,

I don’t know about you, but I usually begin panicking when it feels like I’m standing at the bottom of a giant mountain, and I’m planning to climb to the peak, but I can’t even see the top. It feels impossible. That is, until I remember that’s not the correct approach whatsoever. The only way to start such a mammoth-sized climb is to not think much about the summit on a given day. You begin with one step, then another, then trip over your feet for a bit, and keep walking — no matter how long it takes. That’s basically the only path to progress.

But that doesn’t mean my goal isn’t to climb the damn mountain.

As you may know, my current pinnacle is to sail around the world.

Corey and I just set sail on Wednesday with our cat, Pineapple. We spent nearly a year of grueling work in a dusty boatyard in rural North Carolina rebuilding our 31-foot sailboat, Chérie, by ourselves. We also bet our life savings, sold most our stuff, and quit our careers to dive 100% into this new life.

But I’ve learned that “sailing around the world” is way too much to chew off at once. It’s extremely overwhelming, especially given how much we need to learn and how far we’ll need to travel. This will happen YEARS from now (I hope), but we’re only on day 3 of our amazing sailing journey. Plus, we need to enjoy all the ups, downs, and in-betweens.

So, here’s the compromise: We are only focused day-to-day on getting to the Chesapeake Bay and learning to thrive aboard our new floating home.

That’s not too hard now, is it?!

This week’s Logbook is about how it’s necessary to crawl (but sometimes dance) toward an Everest-sized goal in order to make it feel more achievable and protect our mental & physical health. It’s got some hard-earned lessons already! In it, you won’t hear anymore talk of sailing around the world, because that’s not what we’re doing right this instant. Right now, we’re coming to terms with this colossal change to every aspect of our lives. We’re learning how to sail Chérie to the Chesapeake and gain confidence along the way. We’re still learning how to get started. That’s it. That’s much more manageable and also more enjoyable.

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If you’re new to Radical Paths, welcome! I recently launched the Logbook as a weekly invitation to all subscribers to follow the latest happenings on our wild odyssey at sea. Once I get in my groove on the water, I’ll be publishing other types of articles in addition to the Logbook. I’m planning deep dives into diverse topics, including inspiring stories about real-life adventurers (not only sailors), how to achieve dreams big & small (not only sailing dreams), reflections on living a life with different goals than the majority, and more.

Here’s how it works:

• Paying subscribers: You’ll get ALL my regular articles, the endless archive, and a new Logbook each week.

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This week’s Logbook will be available in its entirety to all subscribers of Radical Paths!You can also become a paying subscriber and check out last week’s Logbook here. 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 my floating family reach our dreams, sustain our adventure, and keep sharing with you all for years to come.

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NOW:

Here is this week’s Logbook:

1. The final steps to the starting line: Letting go was the only way to keep moving forward. But I also fantasized about tapping out.

2. Getting our sea legs (with a side order of fear): We’ve now sailed for 3 days, anchored multiple times, and I thought Captain Corey might die ONCE.

1. The final steps to the starting line

It’s been quite the week. On Sunday, Corey and I handed in the keys to the little house we’ve been renting in New Bern for the past 10.5 months, and we moved aboard the sailboat we fixed up with our bare hands. We also moved our old tabby cat aboard (thankfully Pineapple loves it). We tried our best to organize the stuff we did needed with us on Chérie, and either sold, donated, or gifted the rest.

It might be surprising to you that these steps would be challenging at all. You may be reading this and thinking, “Man, he’s living the easy life!” Someday hopefully! But each of these items on the to-do list felt like lifting a huge boulder in the moment, and it was hard to get my arms around it. These pauses were filled with second-guessing and sentimentality.

But then, like magic, the difficulties all faded.

I’d take a final look at a thing, feel flush with nostalgia and doubt, and then, I’d say good-bye, and move on pretty soon after. Of course, I’ll always think fondly of it. But the jagged edges of those moments faded into the ether. Poof!

And I just kept moving forward.

For example, I sold my beloved Subaru hatchback on Tuesday. This hunk of metal has taken me thousands of miles exploring the U.S., and it brought my little family from Denver to North Carolina to the biggest adventure of our lives. Then, it served as our honorary work truck while fixing up Chérie.

Photo of my old car, all clean and pretty, in front of our sailboat, Chérie, on the final day before I sold it.

But then, riding in the Lyft back to my sailboat, carless, it hit me: this was absolutely the right move. Selling my car was the only way to keep moving toward my goal. And, in fact, selling it paid off all the bills we had accumulated in the final 2 months getting our sailboat ready to go!

All these good byes became more like thank yous.

• Thank you to the rented house that we called home for the past 10 months, and our kind landlords, while we worked toward this dream.

• Thank you to all the stuff we found useful enough to bring or buy while here, even though it no longer serves a purpose.

• Thank you to my car!

These salutations are sincere because they got us to this moment, where I’m writing this newsletter aboard Chérie, anchored 22 miles away from where we fixed her up, with my husband plotting our next sail and Pineapple sitting beside me on my hand-sewn cushions.

Thank you, thank you, thank you.

However, multiple times this week, I fantasized about how relieved I’d be if I just tapped out.

Almost instantly, though, I knew that wasn’t the answer. The second-guessing, doubts, feeling the weight of the challenges ahead — it’s gotta be normal when doing something this big. But I’m here for the adventure and the self-discovery. I’m so damn curious how all this will turn out and the endless surprises coming down the pike — good, bad, or indifferent.

The only way for me to find out is to keep on stepping forward. Hurdles, then lessons. Tripping, then getting up again. Small steps. Sometimes crawling. Then, before I know it, I’ll have made it around the first challenging leg on my way up that impossible mountain.

2. Getting our sea legs

I felt nothing but delight as we left the boatyard docks on Wednesday for the final time. We fired up our engine that Corey installed himself, I guided us away from the docks with my boat hook, and we motored out of the narrow channels to the brackish Neuse River, which leads to the ocean.

We waved good-bye to the boatyard workers as we headed off. Some of these guys were aghast that we weren’t planning to come back. One of the workers told us the “right way” to start a sailing adventure like ours would’ve been to first do some overnight or multi-day sailing trips, then come back to the boatyard and reassess. But no, no way — that’s not how we would do this. And this was one thing we were very stubborn about. If we were going to have problems, it would be somewhere away from where we started. Somewhere new.

When we got to the Neuse River, we decided it was time to turn off the engine and sail. We got out the working jib, which is an everyday sail that connects to the wire cable running from the bow of the boat to the top of the mast. It was a pretty windy day — with 10-15 knots of wind and occasional gusts up to 25 — so we figured we wouldn’t raise the mainsail (the one that you run up that mast). At least, not yet. We could just rely on the working jib to take us, slowly, to our destination.

Given we had just left the boatyard, and we’d only begun a new phase of learning how to thrive on the boat, we were in no hurry — at least in theory.

So, we turned off the engine, felt the wind fill our working jib, and got Chérie to about 4 knots, which equates to 4.6 miles per hour. This might not sound like a lot, but our little sailboat is only designed to sail optimally at about 6 knots. And if you’re crossing oceans at 4 knots, on average, that means you can cover 110 miles in a single day. That speed is excellent!

Photo of the captain, and my husband, Corey — at the helm of our sailboat.

We sailed to the coastal North Carolina town of Oriental, where we planned to spend a few days practicing some sailing. This area is right near the Pamlico Sound, which is a stretch of water protected from the open ocean by a string of narrow islands off the coast. It’s sometimes super windy and choppy, but we figured it would be a great place to break in the boat for the first couple days.

We made the 22 nautical mile journey in a single day. I felt like a champion having finally sailed on a one-way trip to a new spot on the map!

But, for about a 10-minute period, I honestly thought Corey might fall off the boat.

We had become impatient with 4 knots. Going down wind, it didn’t feel that exhilarating. So, even though we knew it’d be gusty, we ended up hoisting the mainsail, little by little, then reassessing our speed and vibes, until we got the sail all the way up to the top of the mast. We got Chérie going to 5.5 knots (6.3 mph), which felt incredible. And it went off without a hitch — at least, for the first few hours. But then, the conditions got choppy.

Photo of Chérie from the deck, with the working jib and main sail hoisted to the top.

I should remind you again that Corey has more sailing experience than me, but he admits he’s not an expert sailor. He used to sail small dinghies in the Boston Harbor with no instrumentation, and he was a boss at it. I’m still learning. I knew the lingo, some basics, but not all the actions. So, this part of the journey is about both of us getting up to speed and becoming a solid sailing couple.

But as we were approaching Oriental to look for our anchorage, the winds picked up and the water became dicey. While I was in charge of steering, Chérie heeled over a couple times, meaning she turned about 60 degrees on her side as the wind roared. Corey talked me through how to get out of it, but it really flustered me. I heard a bunch of stuff below deck falling to the floor, and poor Pineapple started howling, likely terrified about what was happening to her new little house. I was also freaked out!

Given our level of experience operating Chérie, we decided to get the sails down ASAP and fire up the engine so we could approach our anchorage with full control of the boat.

To lower the sails, though, Corey needed to go out on deck in the tough waters, and I needed to stay at the helm with a single order: just steer into the wind. Steering into the wind would de-power the sails and make them much easier to pull down. Plus, we wouldn’t be at risk of sudden jerks or more heeling. But I was shaken up. The steering control is opposite by design, meaning that you need to pull the tiller if you want to go the OTHER way, and the wind instrument has an arrow pointing the direction the wind is coming from relative to the boat, which is confusing to interpret as a newbie. I couldn’t figure out how to keep the boat in the wind with 100% certainty, given my brain was so frazzled.

I asked Captain Corey if we could wait 5 minutes before he went out on deck and he said “No, we can do this.” And then he went out on deck.

I stayed at the tiller aiming Chérie into the wind, and sometimes, I admit, I was guessing which way to pull the boat and just keeping my eyes on the wind gauge to tell me whether I was right or wrong. I couldn’t think. I didn’t have my intuitions yet. This was NOT second nature.

There was a point when we started to heel over again while Corey was out on the deck, and I pictured him falling off the boat. These sorts of man-overboard situations can be huge disasters, especially in waters like these. I wouldn’t have been able to get him. I saw my whole future flash before my eyes without my husband, my best friend of 17 years, and this was a thought I couldn’t bear. My soul would wither into nothing. I’d also want to die. And yet, I realized the intense gravity of the moment we found ourselves in. His fate — our fate — was in the hands of Mother Nature, me at the helm, him on the deck, and the result of decisions we made together this time last year to sail a small fiberglass vessel across big bodies of waters with limited skills.

But he got back to the cockpit. He had pulled down the sails without any issues. He had a huge grin on his face and said, “That was hairy, but good job, babe.”

We debriefed about this after and we now realize we made some unwise decisions. In addition to having too much sail up, we didn’t have our life vests out, nor our safety harnesses setup. We were obviously OK. Corey was grabbing onto the boat the whole time (“one hand for the boat, one for me”). But we put ourselves at extra unnecessary risk. Stupid, stupid, stupid. But we learned these lessons the easy way. We have a sailor friend who has told us, “I learn a new hard-earned lesson everytime I’m out sailing.” But we’ll never do anything like that again without the proper skills and protection.

I understand that this is not how many folks would advise us to learn, and it may sound a bit too extreme, but this is how we’re doing it.

The next day, we went out and sailed again in even stronger winds — with 15-20 knots of wind and occasional gusts up to 30 — but we only put up the working jib. It felt like we were flying at 4.5 knots! And I freaking killed it at the tiller, guys. I learned so much on that outing, like how to prevent heeling and how to keep the working jib from fluttering. We crossed the wind multiple times, which involves some skill, and it got my confidence way higher. We had an amazing sail — even through choppy waters.

But in this moment, I can’t tell the difference between courage, confidence, or stupidity. Is it possible we’ll regret taking this approach sometime soon? Absolutely! But I have immense faith that we’ll figure this out.

Learning to thrive aboard Chérie will include taking baby steps to becoming more-expert sailors. We will fight the impatience that we learned in our previous career-centered and busy city lives. We’ll take our time going forward and not put ourselves into situations that are too risky.

But every aspect of this new life — or any life — can be challenging, full of risks, and contain hard-earned lessons. A couple people we know who have done what we’re doing for a long time said the most risky thing they’ve ever done in their lives was to drive 65 mph on a two-lane highway.

We know we’ll never get to zero challenges, no risks, or eliminate all mistakes. We just need to do what we can, work together, and learn from our lessons.

As we were looking for anchorages around Oriental on our first night, we realized quickly that this would be another challenging part of our sailing life. Finding a good anchorage, avoiding the endless crab pot buoys, setting the anchor, and ensuring that we weren’t dragging — all of that is a lot!

The second night, though, we motored through some really treacherous waters where the depth got down to 1-2 feet to the left and right of us, and I steered Chérie like a boss. We anchored in a beautiful spot with no one around us. We swam around the boat. We showered in saltwater using our solar shower bag and it was spectacularly rejuvenating. The wind got up to 30 knots and it rained overnight, and our anchor still held as firmly as our resolve.

Photo of author (left), who is the first mate, and Corey, the captain of Chérie. This is us at our beautiful anchorage near Oriental, NC. We freakin’ made it!

Until next time,

—Cory Vinny

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