How Our Challenging Southern Town Looks From a Sailboat on the Water
We needed to roll with uncertainty & imperfect choices becoming seaworthy in coastal North Carolina
Many years ago, my husband first floated the idea of sailing around the world and I initially said “No way.” Then, I laughed and told him, “I guess maybe when we retire?” My reluctance came from having no clue how anyone in our situation would begin such a wild & new journey. It sounded too extreme. I thought we’d need millions of dollars and decades of practice. But it wasn’t true. We just needed to make a decision to start.
How do I know? Because this time last year, we decided to dive in head first. Now, we’re only 2 weeks away from setting sail from coastal North Carolina.
Self-reflection and a bit of serendipity led me to change my view of this sailing dream. Our lives had become too predictable in Denver, Colorado. We opened the door to turning our routine on its head. We rediscovered the sailing idea by stumbling upon totally normal people on YouTube who had built sustainable, adventure-filled lives cruising in their sailboats at sea. Then, we decided we had the gumption to join them.
The sailors we discovered online weren’t extremists. They weren't rich. They weren’t experts — at least, at first. They were folks motivated by a new challenge, who embraced the adventure, and rolled with all the newness and imperfect choices that came their way. The uncertainty was a feature, not something to fear.
It inspired me like nothing else I’d experienced in years.
Our small sailboat could be our home, transportation, and adventure pod, and we could take it all over the world?! How much cooler can life get?!
So, after completing some initial research, we decided to go for it. But Phase 1 required us to pick a prime place near the ocean to start.
I had devoured Rick Page’s book — called Get Real, Get Gone — about how to become a sea gypsy, where he suggested:
“Buy a boat somewhere nice, where it is cheap to live, that has lots of easy sailing and move aboard.”
Good advice, Rick! But where?
Picking a place to start was one of the most baffling parts about beginning this journey, because every option had its drawbacks. It was the first instance of us converting general advice into something that made sense given our situation. But it was also a prelude to every decision we made going forward. There would rarely be a perfect decision in Sailboat Life. So, we first relied on self-reflection and came up with the following personalized constraints:
Cost. We’d need to find an affordable, furnished place to live while refitting our sailboat ourselves.
Location. We’d need it to stay in the U.S. so I could keep my remote job while getting the boat ready, and preferably it wouldn’t be a place wiped off the map by a hurricane or buried under blizzards.
Resources. We’d need a decent selection of used sailboats, a friendly DIY boatyard, and accessible supplies & expertise.
But we still had trouble finding a place that checked all these boxes. So, one year ago this week, on May 28, 2024, I posted a question in the Cruisers Forum — an incredible online resource for the diverse people of this unique subculture.
Here’s an excerpt from my post:
Over the following week, the good folks of the Cruisers Forum populated my post with 5 pages of comments. It was immediately clear that everyone had their own particular tastes and constraints.
But respondents instantly talked us out of Florida. It was too expensive, crowded, and the extreme weather risk was too great, especially considering we were making our move at the beginning of the 2024 hurricane season.
Other folks talked us out of the Pacific Northwest and New England for cost- & weather-related reasons. Plus, these places were further from the Caribbean!
And then, a bit of serendipity struck again when someone proposed the small Southern town of New Bern, North Carolina.
Decent boating?
Inexpensive living?
Moderate weather?
Check! Check! Check!
But honestly, I had my doubts.
I hate to admit it, but I was freaked out by the idea of living in the American South. I could tell from the map that New Bern was in a super conservative part of the country, which would be a cultural change coming from Denver. Considering I was one half of a same-sex couple, it gave me extreme pause.
And it wasn’t based on nothing. Back in 2014, I had turned down an offer to go to North Carolina for grad school because the program director said it was possible my husband and I would have trouble finding a place to rent because of anti-gay discrimination among landlords.
Would that stop us this time?
New Bern still checked other boxes.
Then I Googled some pictures.
Not bad, huh?
We decided that this new chapter meant we’d need to embrace newness & uncertainty in different ways. I knew from my past that I often overestimated the severity of how bad something would be, and underestimated my abilities to persevere. Plus, I had traveled to 45 U.S. states by that point, including in the South, and I found things to love about it — like the food! And, on our global sailing journey, we’d often be docking in cities, countries, and regions that wouldn’t have the best reputations or be most welcoming to two queer liberals.
But we chose sailing because we were motivated by new challenges. We’d need to learn to roll with all the newness that came our way. This was all part of the adventure! And we’d need to make up our own opinions!
So, we gave it a shot.
Now, it’s been 10 months since we packed our car and drove from Denver to New Bern powered by a dream.
Though we found many aspects to love about our lives here, it’s also the place we’d experience 100 sailboat-related setbacks. And the city had its annoying quirks. But now that we’re approaching the finish line, we have a different perspective on all of it. For example:
We went over-budget on the sailboat, but it always could’ve been worse. After we bought our boat, we couldn’t move aboard right away, like Rick Page suggested. Sitting on stilts in the boatyard, we soon learned we’d need to get a new engine and replace basically every major system on our sailboat. Oops. But it would’ve stung more if we were paying double for housing or marinas in Seattle or Florida. Living in relatively cheap New Bern allowed all the money that I made while working remotely to pay our bills—including boat bills. Win! [🏆]
The beauty wore off, but the area had its plusses. I’ll never forget the initial allure of arriving in the South last summer. The sound of the bugs made me swoon and the humidity felt like a cozy blanket. But then, it became so routine. I’d notice the beautiful sunsets less and less. The people weren’t super welcoming. And our best meals were ones we made at home — not in restaurants like I expected. But thanks to New Bern for being out of the way of hurricanes and blizzards, and for all the easy sailing. [🏆 🏆]
The town may have passed its heyday, but it still helped us across the finish line. The sailing ecosystem of surrounding marine shops & artisans were disappointing. We’d need to drive 2 hours each way to find a guy who could tweak the pitch of our propeller because the guy who used to do it in New Bern had retired. The sailmaker in town almost convinced us to trash our sails even though they were perfectly fine to get started. But our DIY boatyard was cheap and we often found expertise when needed — including from the sailors who passed through over the last 10 months. And the important thing is we got it ALL done. [🏆 🏆 🏆 ]
The reality is that, no, New Bern wasn’t perfect. We didn’t get any explicit anti-gay discrimination like I feared, though it still isn’t somewhere I want to stay forever. It’s not a good fit long-term given my particular tastes and constraints. But, again, perfect was never the goal.
We only had imperfect decisions on where to start our journey, and this is the way it’ll be going forward as well. All we can do is make the best decisions possible with the available info. But the most important thing is that we keep a good attitude, find something to laugh about through all the setbacks, and keep pushing through in pursuit of our goals.
And now, we’re ready for more!
Re-reading that May 2024 Cruisers Forum post makes me so proud of all we’ve achieved over the past year. What an adventure already!
In that post I said:
“[W]e’re going to move near water and learn everything about sailing for 6 months to 1 year…. Then — assuming we’re still as stoked about it — we’ll plan to sail away ‘forever’”.
Ten months later, we’re still stoked about it, so…
A couple weeks back, we finally got the view of New Bern that we had been working toward for close to a year — a view from the water. And it was one of the most gorgeous views of a place I’d ever seen.
It was like getting a new pair of glasses. I couldn’t wipe the smirk off my face.
New Bern looks better from the water now because of how far we’ve come to get here. It helps also that I’m more distant from the financial setbacks, loneliness in a new city, and confusion about how to reach the next phase.
Now that we get to sit on our sailboat on the water, those old challenges are no longer mine. They belong to a previous self who is grateful for all the experiences and lessons learned. And I know that’s how it’ll soon be for every new challenge coming down the pike.
I have a new attitude about all the upcoming uncertainty as we continue on Phase 2 of this journey. This will be the time to learn how to thrive aboard our sailboat beyond New Bern. But now I have much more confidence in my ability to make anything work. And I welcome all the self-reflection and serendipity that will happen along the way as we begin to sail around the world.
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Great post Cory, it’s always interesting to hear the backstory.
Love this, Cory! It's so important to celebrate our wins along the way. And your new perspective, as you're looking back from your boat, is priceless.