We're Now On Our First Open-Ocean Voyage and Ready to Improvise Like Jazz Players (If Needed)

⛵︎ Logbook 8/10/25: 54 days into our global sailboat odyssey

Ahoy fellow explorers,

The prospect of our first multi-day passage on the open ocean was equally thrilling & intimidating. It felt like a final exam you studied for and yet knew the teacher was the type to throw a few curveballs. But Corey and I built the necessary foundation. We compared notes. We tracked the relevant signals to gauge our environment. All we could do was walk into that exam hall when the teacher told us that it was time. And in our case, when Nature presented a decent weather window, we’d begin flying our little sailboat, Chérie, the 120 miles across the salty waters to New York City and directly through whatever surprises she threw at us.

If you’re reading this on or soon after Sunday, August 10, we already departed from Cape May, New Jersey, and will be well on our way.

The reason this passage on the open ocean is so significant, however, is not just because we’re sailing to New York City. Sure, we’re thrilled to stroll Manhattan, eat the best pizza in the world at Bleecker Street, and reflect on how incredible it is that we made it there in our little sailboat from North Carolina. And yes, it’ll be the first time we’re so far from land. We’ll have a lot of other firsts, too, like sailing for >24 hours straight.

But it’s also a big moment because sailing on the open ocean will soon be the norm.

Fewer than 8 weeks ago, we knew very little about sailing or operating Chérie, and now, from here, we keep climbing up the East Coast, continuing to learn all of her joys & quirks. Then, when the prevailing winds shift in September, we’ll have more multi-day passages on the Atlantic back down south as the hurricanes stop throwing their tantrums for the year.

Then, we’ll head to the Caribbean and beyond.

If this voyage has taught me anything so far, it’s that we’ll never feel 100% ready, but that can’t stop us from pushing forward.

This week’s Logbook is about anticipation. It’s about that feeling of knowing a big moment is imminent and not being able to predict how it’ll turn out — including the challenges, lessons, and splendors to come. It’s about knowing when you’ve done your best to prepare, and then trying to tap into that ancient wisdom of letting things go their own way. It’s also about understanding why we’re all able to improvise better than we imagine. And it includes lots of new pics of the furry crew.

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Thanks for reading Radical Paths! The Logbook is a weekly invitation to follow our latest happenings on the water during our global sailing odyssey. If you missed last week’s Logbook, check it out here:

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

In the coming weeks & months, in addition to the Logbook, I’ll keep cooking up more articles with inspiring stories about real-life adventurers, that offer guidance on how you too can achieve your “crazy” dreams big & small, and 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 still love to hear from all of you in the comments. And thanks for reading along!

This week’s Logbook will only be available in its entirety to paying subscribers.

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.

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NOW:

Here is this week’s Logbook:

1. We finally entered the American Northeast: We transited the Chesapeake and, before we knew it, sailed through 2 new states. Looking at our little dot on Google Maps makes me super emotional. And it fills us with smiles.

2. Anticipating showtime (though, by the time you read this, we’ll already be gone): We waited for the weather window to NYC. We sat in anticipation. But we realized when it was time to hand it over to Mother Nature and believe in our ability to improvise, if needed.

1. We finally entered the American Northeast

We didn’t know our final days in the Chesapeake Bay would come as soon as they did. We had some fast passages from Annapolis to the mouth of the Chesapeake & Delaware Canal. The currents were looking good, so we went for it. Then, we entered a new body of water that was much different and less hospitable. And that final leg to Cape May was nothing like we expected it to be.

In just a few days, we moved from Annapolis, out of the Chesapeake, through the Chesapeake & Delaware Canal, and to Cape May, New Jersey.

The Delaware Bay is a 60-mile stretch of saltwater that we knew would be rougher than places we’d experienced up until that point.