Get yourself a thirty-footer and go!

By Matt Bracken


This essay is directed to all freedom-lovers, but primarily to young unmarried American men. (At my age I count thirties as young, and would readily grant special dispensation beyond that.) It’s dedicated to the guides who showed me the stars, and to thirty great years of both calm and stormy weather.

If you are a Millennial who feels that the Land of Opportunity has at least temporarily suspended the offer, leaving you stranded in somewhat less-than-hoped-for circumstances, I’m writing this for you. Maybe you did the Sandbox trip, and maybe you didn’t. Set that aside. But nonetheless, America has left you feeling like an unwanted cat or dog tossed out of the family SUV at a distant highway rest stop. If that’s you, then let me suggest a novel idea for making a fresh start, one that is particularly well suited to a young man in these uncertain times.

A bit of bio for context. I learned to sail on the Chesapeake Bay in the 1960s and ’70s by accepting crewing invitations with a relative here, a friend there. From Sunfish to Hobie Cats to my beloved Aunt Louise’s Columbia 26 Panacea, I knew a sheet from a halyard before I was a teenager. Learning to sail isn’t rocket science, it’s more like learning to ride a bike. From dinghies to schooners, the same principles drive sailboats through the water.

Almost exactly forty years ago when I was a junior in high school, I had the good fortune to spend my Christmas break in the Caribbean aboard the 33-foot wooden sloop Maica, owned and sailed by my sister Mary and Dai, my Welsh brother-in-law. Over my vacation we sailed between a half-dozen Caribbean islands and I was first exposed to the cruising scene. This was during the winter of the much-anticipated Comet Kohoutek, and if that name does not ring a bell, you are younger than I am.

Even in 1973, long-distance sailors were already crossing the oceans on everything from steel schooners to ferro-cement ketches to plywood trimarans. Free as the wind is more than just an expression—it’s a way of life for blue-water cruisers! Even then, cruising sailors were producing their own electricity with solar panels and jerry-built wind generators. Diesel engines pushed and powered the boats when the wind wasn’t cooperating.

Other aspects of the cruising life immediately appealed to a young man of sixteen, such as the abbreviated swimwear worn by the suntanned French and Scandinavian girls. I was ready to quit high school and remain in the Caribbean as a hitchhiking sailor, crewing for my berth and board, but Mary and Dai persuaded to finish my education, at least through college, and return to the islands as a boat owner, and not merely as a hand, paid or otherwise.

During a college summer break, I made a three-handed trans-Atlantic voyage aboard Maica with my sister and brother-in-law. College led to the Navy, but soon enough I returned to sailing, first aboard a 35-foot fiberglass sloop with my young bride, and later on a 48-foot steel cutter of my own construction. I’ve been through the Panama Canal a couple of times and I’ve been around the cruising scene long enough to have learned a few things that might not be common knowledge in your possibly landlocked or frozen neck of the woods.

And as a writer of near-future dystopian fiction, I’ve done considerable research into various historical periods that I believe have lessons for the times in which we are living. Here, then, are a few of them I’d like to pass along. They’re not original to me, but I believe they are worth restating to the next generation.

Sometimes new situations present themselves as special opportunities for certain generations. Leaving the old country for the new world. The 19th century’s Go West, young man! American soldier ex-pats remaining in Europe after both world wars. The Hippie Trail across Asia in the seventies. Each presented a unique opportunity for the generation then coming of age.

Today another set of circumstances presents another generational opportunity. It involves a glut of perfectly good older fiberglass sailboats, coinciding with an at-best stagnant economy and worse, the steady erosion of liberty in what we used to call the land of the free and the home of the brave.

I understand that the convoluted sentence immediately preceding this one has just lost the interest of 97 percent of my readers up to this point. That’s okay, the essay is not written for you. Go in peace.

Still here? Good.

Some believe that America is morphing into a socialist police state. Couple the diminishing freedom with the lack of economic opportunity, especially for today’s non-minority, un-preferred, un-affirmative-actioned and basically unwanted excess of young males, and an obvious question presents itself. Why stick around the States during this dismal stretch of history? Why not see the world instead, or at least be ready to go on a moment’s notice?

Another history lesson. Sometimes “getting out of Dodge” and far away from trouble and tumult is what matters the most. Ask the Greeks at Smyrna in 1922 about the importance of booking a ticket out in time. Ask the Russian “kulaks,” or the European Jews, or the Vietnamese boat people, or Christians in the Middle East today about the importance of having a viable escape plan. History repeatedly teaches that by the time freedom is conclusively lost in a nation, the exits have usually been nailed shut to prevent unauthorized travel by “bad comrades” and various other scapegoats for regime failure.

Back in the 1990s I was tied stern-to the quay wall in the inner harbor at Hilo, Hawaii, during a trans-Pacific pit stop. While there, I met a Russian family closing in on a circumnavigation aboard a rather crude and basic 40-footer. It had taken them a number of years to circle the globe from Vladivostok. Before that, the father had built their rough-and-ready but seaworthy escape pod from the scraps he could scrounge.

These mad Russians set out for the freedom of the outer world while the Soviet Union was imploding and the Russian ruble (along with their savings) was virtually worthless. They didn’t stick around Mother Russia’s Far East to endure the chaos and deprivation accompanying the collapse of the Evil Empire. Instead, they took a flyer and they sailed around the world for five or six years, teaching themselves English and French, home-schooling their small children, and working along the way.

So let me say this to any young American man who has read this far: you have it a lot easier than Ivan and Natasha did, Bucko! Today in America the escape pods are already made for you, and they’re cheaper and more plentiful than ever. Right now there are entire fiberglass forests of suitable mini-yachts going for a song, just ripe for your plucking!

So, maybe it’s time to consider getting off that rat wheel you call a job and sidestep the sideways-eight over to where infinity is represented by 360 degrees of ocean and sky, where foreign ports beckon from every point of the compass. You would be joining the worldwide fraternity of semi-stateless expat nomads who have already been out there for years and decades, living off the grid, always mobile, literally sailing under the radar.

Still here? I thought so.

“So how do I get there, Matt? I’m just a cubicle rat trapped in Philly or Phoenix, and I don’t know the first thing about sailboats. How do I go about pulling this off?”

Well, start with the supply side of the equation. (The demand is your desire.) There has never been a better time to find a seaworthy 30-footer and go sailing. They are everywhere, thousands of them, cheap! Why do I pick that size? Because that’s plenty of sailboat for a young man, or for a fellow with a young bride or girlfriend along for the adventure. Thirty feet is enough sailboat to cross an ocean while creating your own electricity, carrying your own food and water, and most importantly, charting your own course and choosing your destination. It’s a big world out there, and it’s not all going to hell in a handbasket. Just ask Ivan and Natasha.

Can you live aboard an even smaller vessel and safely cross oceans? Certainly, but below 30 feet you will usually sacrifice standing headroom inside your boat, and you won’t be able to convince many young ladies to try living aboard a severely cramped micro-cruiser with an interior like a roomy coffin.

But for the record, very tiny sailboats can safely cross oceans, and this is not a recent phenomenon. Read about John Guzzwell’s epic circumnavigation aboard his homemade 17-foot sloop Trekka way back in the 1950s to understand what is possible. Or read the books written by Robin Lee Graham or Tania Aebi or the many others who have successfully circumnavigated on vessels smaller than the ones we are discussing. And those pioneers did it without GPS or long-range communications! Their books and many more about living aboard sailboats and the cruising life in general are languishing on the shelves of your local library, just waiting to provide insight and inspiration to future ocean sailors.

What about vessels larger than 30 feet? In my opinion, the “sweet spot” for a young bachelor of limited financial means is an older fiberglass sloop (single mast, two sails) between 30 and 35 feet in overall length. If you can afford a 40-footer, by all means go for it. You will be able to carry more stuff, your ride across the ocean waves will be more comfortable, and more members of the opposite sex will be impressed with your lifestyle. But your annual outlay for marina fees, bottom paint and so on will be quite a bit higher. Since you will need a financial “cruising kitty” to live on while sailing, you shouldn’t sink every dollar you have into a bigger boat than you can afford to maintain over the longer term.

Why I am I discussing only fiberglass boats? Because unlike previous generations of rot-prone wooden yachts, with minimal upkeep most fiberglass sailboats just go on and on, decade after decade. There are now a half-century’s worth of fiberglass sailboats still afloat or waiting in boatyards for your inspection. This annually increasing backlog means the prices for sound and solid older boats have been going down for years.

A spanking-new name-brand 30-footer might sell for $150,000 today, yet there are near clones of that shiny new yacht selling for between $10,000 and $50,000, depending upon age, make and condition. Sometimes even cheaper (and usually older or storm-damaged) sailboats can be found. But a remarkable feature of even old fiberglass boats is that in most cases, with the steady application of elbow grease and some basic fiberglass and woodworking skills, they can rapidly be brought back to “like new” condition.

This, then, is the gambit, and why this essay is primarily directed to young single men: in my experience very few young women have a taste for enduring the ordeal of rehabbing an old sailboat from keel to masthead. Fiberglass work is filthy and nasty. It is guaranteed to involve weeks or months of hard, miserable work in stifling hot boatyards. Often while in sweat-soaked Tyvek coveralls with a dirty respirator strapped to your face. Fun? Not.

At the lower financial limit of the possible, you will live aboard your vessel in a DIY boatyard while fixing her up. As each section is refurbished you adjust your living and working areas until your older sloop is once again shipshape. Or you might not care much about the cosmetics, you just want a seaworthy boat that is ready for the ocean, and in that case your time in the boatyard will be commensurately shorter. Some projects can be done after your boat is back in the water, and you will get your first taste of living afloat.

How can this plan be executed, practically speaking? First, you need to do some research on the internet until you are familiar with the makes and models and conditions and costs of fiberglass sailboats built over the last 40 years. Then you should travel to the coastal locations where the boats are found.

Start with eBay and other more specialized websites such as Boat Trader. Then visit working boatyards and roam around—you will learn a lot by observing dozens of boats out of the water. A road trip to visit a string of large marinas and working boatyards along a stretch of coastline would be more advantageous than flying in to inspect one particular boat for sale.

After you make your selection, if the boat of your dreams is not yet ready for the ocean (and she won’t be if you bought her on the cheap), then it makes sense to do the rehab work near her location. Overland truck transport is a possible but very expensive option. Most often, boats in rough shape are fixed up in the boatyard where they were purchased, or they might be launched and towed or motored to another nearby DIY yard offering better rates.

If you can already do yacht painting, fiberglass work, wood joinery, diesel repairs or have other applicable skills, you might even get a day job right in the boatyard where your future dream yacht is located, while you live aboard and fix her up after yard business hours and on weekends. It’s a tried-and-true shoestring financing tactic I’ve seen replayed many times in various boatyards over the decades.

But if you have enough money saved up to work on your boat full time without needing an outside income, the project will move ahead much more rapidly. Working on your boat full time also shortens the number of “lay days” you will spend in the yard, and minimizes your ultimate yard bill. Each day in the yard costs money, and “no cash, no splash” is the policy at every boatyard regarding their tenant boats up on the dry ground. (And why a lot of boats in arrears wind up on the used-boat market at divorce-sale prices.)

If you can move your yacht to a friend’s back lot, warehouse or dock where you will not be charged rent, you will save even more money. However, it’s not a trivial matter to haul a 30-foot sailboat over the road, so in most cases, you will initially do the work in the boatyard where you discovered and bought your vessel. Depending on the purchase cost, your marketable skills and other factors, it’s reasonable to estimate that a bachelor on a very tight budget might need six months to get an old sloop ready for the ocean again.

On the other hand, if you can afford an outlay of $30,000–$50,000, you can buy a “turn-key” sailboat that is cruising-ready from day one. This also opens up more options to those who could not or would not contemplate months of filthy boatyard work, including, of course, many gung-ho women sailors bent on the cruising life. If you have an even higher budget, boats over 40 feet become an option. How much equity do you have in that unloved mortgage trap where you currently hang your hat?

A caveat: if your physical limitations mean that sailing the ocean waves is not a realistic option, then sidestep again over to my other top recommendation. Substitute “houseboat” for “sailboat” in the above essay. You will give up the ocean-crossing potential of a sailboat for much greater access to thousands of miles of inland waterways, from Texas to the Chesapeake Bay and beyond. Thousands of miles of rivers, lakes, estuaries, bays and creeks that are physically separated from our crowded cities and highways, if that thought has any appeal.

Don’t overestimate your physical abilities. Sailing on the ocean requires agility and stamina. Bad weather can last for days, throwing up terrifying waves that will challenge both your boat and you. Sailing on the ocean is not for everybody. A houseboat or trawler is for everybody else. You can’t cross oceans on a houseboat, but you will live aboard a mobile and nearly invisible escape pod, moving inconspicuously along the Intra-Coastal Waterway from state to state as liberty and economic opportunities wax and wane.

Whether you choose sail or power, the bottom line is that you can sidestep a decade locked in a cube in Rejectionville by living aboard an old but perfectly sound fiberglass boat that you buy cheap and fix up. You can stop running in place on the government or corporate rat wheel and escape from the matrix of our burgeoning new American police state. At least for now, the only chains holding you down in your dead-end burg are those around your mind. Remember Ivan and Natasha from Vladivostok, and count yourself lucky.

Keep in mind that owning a sailboat that can cross oceans doesn’t mean you have to. But if the proverbial shit ever hits the fan, and the day comes that you need to put on your seven-league boots and head for another country or even another continent, it’s as simple as aiming your bow past the breakwater and sailing straight over the blue horizon.

But before you click over to the websites advertising used sailboats, click over to where you sample music and check out “Sideways Eight” by Echo and the Bunnymen. It’s perfect mood music for discovering infinite new horizons. And while you’re there, check out “Stormy Weather,” “Seven Seas,” “The Killing Moon,” and many other songs performed by the greatest English rock band that most Americans have never heard of.

Now, while those oceanic freedomista anthems are blasting through your ear buds, start looking for great deals on old fiberglass boats. How much cash could you realistically scrape together? $15,000? $20,000? That’s enough to begin searching for your very own escape pod. If you start now, you could be in the islands by the summer of Comet Ison, a round 40 years after my life-changing winter of Comet Kohoutek.

(Matthew Bracken is the author of the Enemies Trilogy, Castigo Cay and other short stories and nonfiction essays. He graduated from the University of Virginia and Basic Underwater Demolition/SEAL Training in 1979. He is married and lives in Florida while plotting his next escape.)

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Dim Witte
Dim Witte
4 years ago

You are dreaming, if older than 30 and want to sail a 30′ on the oceans. Better to be ready to bug out on a week-ender for coastal cruising, using it locally and inland waterways. I like the story about the office worker who went directly to his boat on Friday, changed clothes, sailed downriver to a nearby town and binged, wrote stories on boad Saturday, and sailed home Sunday. Like the story of the retired farmer in Oregon who spent his time working in the barn, which his wife carped about. Then one day he removed one end of the barn and towed away a sailboat on a trailer, never to be heard from again. Investigation revealed that he stopped at a town to fully provision his boat, then went to a landing on the Willamet River and sailed downstream.

4 years ago

As an older guy in mid 40’s who learned to sail, I think one must be extremely physically fit and agile to be able to do this. That and have a large cash stash to buy provisions and spend the time. It is not viable option for most people.
3 years ago

I found my boat .. now how am I going to get sailing lessons this sounds expensive and I’m putting my savings into the boat I want to live on