My Biggest Barricade To Exploring Forever At Sea Was In My Head (Not My Wallet)
Wind Hippie and Sailor James force us to reconsider our real obstacles
One of my favorite modern stories about a young adventurer is someone named Holly Martin, A.K.A. Wind Hippie.
In 2018, she set sail alone from Maine on her small, 27-foot sailboat named Gecko. She spent 10 months fixing the boat up herself. When she finally left forever, she was in her mid-20s and it was only her third time sailing alone.
Before heading out, her dad spent 45 minutes showing her how to use her self-steering system, called a windvane.
Then, she sailed south 2 days later.
She first voyaged 1,000 miles down the North American coastline to North Carolina. She figured it out alone day-to-day, anchorage-to-anchorage, and without certain amenities like refrigeration, Starlink, or a motor on her dinghy.
Sailor James, in an interview last year with Wind Hippie in New Zealand, responded to her origin story by saying, “That doesn’t surprise me that you did it that way.” He said, “You’re pretty wild.”
She laughed in tacit agreement.
Sailor James is a relatively young guy who also left alone on a small, 30-foot sailboat, Triteia, for a global adventure. He first voyaged from Los Angeles to Hawaii. Before leaving forever, he had sailed as a crew member on other people’s boats. He was coast guard certified. But his boat was also simple.
These two sailors understand each other.
Wind Hippie and Sailor James had <$2,000 in cash the day they set sail.
Both sailors now have been voyaging safely & sustainably for >5 years.
Their stories showed me I could do it, too.

At this point, I’ve found countless stories scattered across the internet and in books that helped me realize that the barriers standing in the way of my sailing dreams were much smaller than I thought.
Before getting started on my sailboat adventure with my husband and cat, I thought this lifestyle was only for the wealthy or retired.
But Wind Hippie, Sailor James, and others showed me that’s not true.
Their stories energized me like mainlining a liter of Red Bull.
In the interview, Wind Hippie explained to Sailor James that her original plan was to circumnavigate, but she had no exact plans. She said, “The joy of living on a boat is you don’t have to have a timeline.”
This attitude makes me swoon.
But I also hear the disapproving voices of so-called sailing gurus in my head saying, “Stop!” “You shouldn’t do it this way!” “You need more experience!” “You need more money!” “You need more crew!”
They swear that their way is the only way.
These doubts often swirl around in my head (and they’re often in my dad’s voice, but that’s another story).
Wind Hippie and Sailor James show that we can sail away forever with more or less experience and resources — as long as we’re not total idiots. And we can do it at an age when most people are wasting away in a cubicle somewhere.
But the crazy thing is there are countless stories of people like this who leave with what they have and just figure it out as they go along.
In the interview, Wind Hippie and Sailor James talk about how there are 1000s of people out there without YouTube channels doing exactly what they’re doing.
These sea gypsies are folks of all ages, genders, experience levels, and budgets. And they make it work, as long as they have the basics and a good head on their shoulders.
You can buy a seaworthy sailboat for the price of a new Honda Accord.
You can learn to sail fairly easily on small dinghies, crewing on other people’s boats, and taking it slow.
Once your boat is reasonably safe and you are a fairly competent sailor, you can join them, too.
And it doesn’t take THAT long or require much money to sustain.
It’s more about your attitude.

Wind Hippie still had basically no money when she made it to the Caribbean, but she said she wasn’t worried about her small pile of coins one bit.
She only spent her cash on food that she cooked on her boat.
No restaurants. No bars. No marinas. No rent.
But so much freedom.
She figured she’d do manual labor on boats when she needed more cash.
In the interview, she told Sailor James, “I figured I’d run out of money and just figure it out. To me, that was part of the adventure.”
“I just wasn’t worried about it”
And she did figure it out. She’s now going on year 7 at sea.
In that time, she’s been through a lot, too.
She’s made it through countless storms on her little sailboat.
I watched a series of her videos the other night where she traversed to New Zealand with no engine, a ripped sail, and her windvane was held together with a plunger handle.
In the interview, she recounts a story of her passage to the Marquesas Islands, which was a 4,000 mile solo passage that took 41 days, and her self-steering failed. This meant she needed to sit at the helm for 1.5 days straight at one point to keep the boat pointed on the correct path. She was so tired that she didn’t even realize she passed the equator, which is normally something that a sailor enthusiastically celebrates.
When Wind Hippie finally made it to land, she said it was one of the most amazing feelings in her life.
But she’s not a fearless psychopath — she just wants this life more than anything else.
In the interview, she told Sailor James about her safety concerns of being a solo female sailor — not from Mother Nature but other humans.
She said sometimes she has locked herself in her boat, because she didn’t feel safe. She sometimes will tell other boaters in an anchorage, “Hey I feel a bit uncomfortable tonight, can you leave your radio on?” (They always say yes.)
But she told Sailor James her safety concerns aren’t enough to change her lifestyle.
“I can’t let that stop me, because that would be sad.”
We’re not solo sailors like Wind Hippie and Sailor James, but I am 100% connected to their motivations for voyaging forever at sea.
Don’t get me wrong — I’m not looking forward to the horror stories. But I am looking forward to getting through them.
I’ve heard a couple sailing gurus tell me that that they’ve been sailing for decades and never been in a storm.
I’ve also heard experienced sailors say there’s nothing more exhilarating than being in a storm when you trust your boat and everything is going right, then you make it out.
I’m looking forward to the memories.
I think we’ll be much better prepared than Wind Hippie and Sailor James in many ways — that is, if we can maintain our kickass attitude.
The last 10 months, we’ve been fixing up our small 31-foot sailboat, Chérie, on the North Carolina coast. We’ve replaced all the major systems from keel to mast.
Unlike Wind Hippie, we’ll have a working engine, reliable windvane, and decent sails (we think).
Though we’ll be living on a similarly small budget as both of these solo sailors, we’ll have a larger financial runway to start. Did we need that much runway? Their stories suggest maybe not.
Our list of boat projects is also quite long. We’ve completed all the projects that we deemed absolutely necessary to get going. However, like Wind Hippie, we’re leaving next month without refrigeration, Starlink, or a motor on our dinghy.
We’ve already had sailing gurus telling us, “You will need that stuff.”
But it’s clearly not true.
I’ll tell these gurus about people like Wind Hippie, and they’ll say, “Well, that’s not the most enjoyable way to do it.” Or, “you’re making it rougher than it needs to be going without.”
Oh really? Well that’s much different than “YOU NEED IT!”
But we’ve considered all this super deeply (and looked at our budgets), and we’ve decided that we don’t want these amenities if we can live without them.
We only want to build complexity if we need it, because it sounds more fun and it’s less stuff to break. Plus, we want to go now!
Wind Hippie and Sailor James show us that you must believe you can do it — no matter where you begin.
Of course, you need basic sailing & survival skills and a reasonably safe boat. But that’s not super hard to get there.
The most important thing beyond that is an optimistic attitude, strong work ethic, and a mindset focused on keeping the dream alive.
We must believe we can do it, too.
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Definitely going to check these two out more
I truly can’t wait to read about your first night at sea! This is super exciting.