This past month, I woke up in the pre-dawn light on the morning I turned 55, and found a chartreuse post-it note affixed to the table in lieu of a birthday card or gift.
Certain adjustments need to be made for life aboard without stores, cars, or Amazon delivery. I was just glad Colin had remembered the date.
Then I read it. And one little post-it turned into the best gift I’ve received in a decade.
To explain why, I have to take you back to March of 2020. Colin and I were in La Paz, Mexico, near the bottom of the Baja peninsula, aboard our first boat, provisioned up and ready to cross the Pacific to Polynesia. I’d just written a blog post titled It’s Go Time!
Around three thousand miles to the Marquesas lay ahead. Four weeks at sea. One of the longest ocean passages on the planet—and we were ready.
Then Covid closed the Pacific, and almost immediately, Go Time became STOP. Like a game of red light, green light.
So we pointed the bow north instead, toward Los Angeles. Not the next harbor on the way somewhere, but the end of our cruising life for as far as I could see into the future.
I remember thinking as we left La Paz, I’m okay with this. I’ve accepted it.
And then, that first day sailing away, I sat on the cabin top and bawled my eyes out, flooded with grief for the life I loved. The one I knew I was losing.
The years since have brought many wonderful things. Family and friends and writing. But it always felt like a smaller life than our cruising days, and I never stopped feeling just slightly caged.
So when Colin decided we needed a bigger boat to re-start our life at sea, I made an uncharacteristically massive bet.
For all my adventurous spirit, I’ve always been pretty conservative with money. In my twenties I bought real estate instead of cars or clothes. When I earned more, I allowed myself a few luxuries and stashed the rest away for financial freedom—back before anyone had thought to call it FIRE*, much less ignite a movement. Even our first boat was bought on a modest budget, with the house kept as a rental. Always a Plan B.
This time, I sold the house to upgrade the boat. Traded the appreciating asset for the depreciating one and put all my chips on black.
It was either the gutsiest or the stupidest thing I’ve ever done.
Then, I waited.
It took years to get our new boat and in the process, I’d lost much of my sense of who I was. By the time we took delivery of Pristine in January, Colin and I were both exhausted shells of our former selves. This first year turned out harder than either of us expected. Gales, tides, currents, boat problems, and bodies many years older meant fatigue hit harder, recovery took longer, and resilience was a fraction of what it once was.
When people have questioned our choice, I’ve always held a confident, defensive line in the sand. But here’s the part I don’t often say out loud. There have been times since that first red light when I wasn’t sure we’d make it back. Then, times I wasn’t sure we wanted to be there at all.
That’s the underlying stress I was carrying, that birthday morning, when I read what Colin had written on that Post-it.
“Happy birthday, my love. Thank you for dreaming so big. You make us all bigger and better. I’m so happy to be here with you.”
This time, the tears were the good kind.
Pristine, for her part, has been raring to go all along. On a light-wind day from Madeira to Lanzarote last month, we hoisted the gennaker, and she bombed along, joyous as a Goldendoodle with her head out the window. Every boat has a hull speed that physics says she can’t exceed, and Pristine’s is around 8.5 knots. We spent most of that day doing that and more. Then every so often a wave would pick her up, she’d surf well into the 9s, and physics would have to look the other way.
If you read the last letter, you know we were waiting to find out whether Colin’s swim-ladder fix had cured the leak. The verdict: mostly. We’ll sort out the rest somehow. For now, we’re well on our way, and once again looking forward to an ocean crossing. This time the Atlantic. Sometime after Thanksgiving-ish.
Meanwhile, The Navigator’s Ellen has been waiting on a green light of her own. The last time you saw her in these letters, back in June, a nor’easter was picking the pins out of her hair on a South Street quarterdeck, and I’ve left you standing there with her ever since, waiting for the next book in the series.
I know a thing or two about long waits now, so I’m happy to announce that A Course to Steer, Book 2 of The Navigator Series, finally has a launch date: February 6, 2027.
Green light. 🚦
Fair winds,
Cheyenne
*FIRE stands for Financial Independence, Retire Early.
P.S. What dog face are you happiest to see panting out a car window? Dachshund? Boston Terrier? Shaggy mutt? Hit reply and tell me. I read and respond to every one.
P.P.S. Spare a thought for the real Eleanor Creesy on October 7. At 10 a.m. Eastern, when she will finally—175 after her record-breaking voyage—be inducted into the National Sailing Hall of Fame. It’s a huge milestone for women’s sailing overall, too, so raise a glass next Wednesday. And if you’re so inclined, feel free to celebrate with friends, on social, or better yet—with a sail of your own!

Our sailing route is a lot less legendary, but just as full of adventure. :)







This was the other half of my birthday, by the way—sushi dinner. Clearly, I didn’t like it at all.

One more green light, and this one is all yours.
Speaking of history's nearly lost heroines, I’ve teamed up with a group of authors who write novels about them. And we've all made our books free through December 15. Unforgettable Women of History—find yours here.
