Flipping Sail: The New American Dream

Excerpts from Sailboat Cowboys

Published in the August 2018 Issue March 2020 Feature Vanessa Oler

We learned that we have contempt for the word “can’t” and the people who use it. If you have a work ethic, are able to see absurdity and laugh and can think outside the box, then you can flip sail. We knew what we were after and modified the path as we learned. And we never gave up.

We watched Storm Sandy hit the east coast with its frightening intensity. More than 50,000 damaged boats was a mind-boggling number. We began looking into this weather disaster and the possibility of getting that yacht we deserved. We originally planned to have a paying vacation and see that part of the country by repairing and selling just one damaged sailboat, not the 15 we ultimately flipped.

I was born and raised on the Gulf Coast and had owned boats and grown up in the world of beaches and water. I had trade skills and the idea of living on a cruising sailboat while repairing it had the advantage of affordable living with the aura of a romantic adventure. Girlfriend was Arizona born and raised and when I brought up the idea of flipping damaged cruising sailboats on the east coast she said, “Cool! Count me in!” Bless her heart. Never mind that our kids were scandalized, called us “old hippies” and quit talking to us… we had the dog!


We began living with the insurance companies and their auctions, marinas, buyers and sellers and learned the goals and motives of the people in the world of sailboats and made it pay. Dealing with sailboats and the sail community is often more art than craft, unlike the more worldly and practical powerboat market. We found ourselves puzzled and laughing often as we pampered ridiculous people who thought they were going to sail off into the sunset to lie in a hammock, swill rum and live “The Dream.”

“Play it by ear,” was said often and became our mantra. We found prospect boats north of the economical do-it-yourself marinas on the lower Chesapeake where we began to repair them and that in turn was often north of where we sold them in the sailing Meccas of Pamilco Sound and the mid-Atlantic coast. We let this be our excuse to travel on a sailboat, easily convincing ourselves to sail a boat north or south for “business” or to “a better market area.” We became familiar with the eastern waterways of America from Buffalo, N.Y., to the Carolinas then Savannah, Ga., and down to the Tombigbee River to the Gulf of Mexico at Mobile, Ala. From there, we traveled west along Mississippi’s casino strip and around New Orleans, La., and the mouth of the Mississippi River to Aransas Pass and Corpus Christi, Texas. The different sights, geography, and people we encountered became the focus of flipping sail; the money we had down pat by this time.

Living on a boat while repairing it makes sense and it's as fun as camping out. We made the interior livable in short order; the head needs to work and you have to be able to make coffee. A color-matched microwave and refrigerator from Walmart takes care of the cooking and is a major selling point. We use a French press for making coffee so we can heat water either on a propane camp stove underway or in the microwave at the dock.

On our first epic journey down the Intracoastal Waterway of America’s east coast we went prepared with no more than a batch of notes, thrift store charts and a cell phone. We didn’t have a VHF radio or a depth finder. The angels must have been charmed by our innocence.

The Erie Sideline

The owner of this sailing school in Buffalo, was a talented and eccentric character for whom we soon developed a sort of protective instinct, often protecting him from himself. We developed an affection for the members of the sailing school, they were too decent and funny not to feel kily disposed toward. They had more “captains” and “commodores” than the English Navy and were enthusiastic without any harm. I would wander through knot tying class and throw together something unusual and they’d again have their notebooks out like E.F. Hutton was speaking. I know. It was an ego thing.

By this time, I’d repaired every mechanical issue that plagued them, which never amounted to more than a few minutes and had them opping with delight. We picked out a 1978 Mariner 28 from among the donated boats and repaired and registered it. We looked at the Erie Canal on the Internet… the history, scenery, the canal towns with ehri free dockage complete with electricity and had put it at the head of our must-see list the year before. The great thing about doing this with boats is the opportunity to talk ourselves into doing this you just want to do, telling yourself it's in the best interest of selling a boat. We’ve been from Buffalo to Corpus Christi because we decided a boat would sell better around the next corner, bay or ocean.

I slung a rope between a tree and another boat to let the mast down and secured it on deck for the trip down the Erie Canal. A member of the school asked me how I got to do this and how much it had cost. “Let’s get one thing straight,” I said. “The very thought of anyone getting close to any of my vehicles, boats, or even my lawnmower with so much as a screwdriver in their hand makes me nervous.” He backed off like I was some kind of nut, which I guess I am.

This stuff is so easy. That sailboat was within $400 and four days of work from being viable and it had sat neglected and useless for ten years. A thousand dollars would have bought it. We motored and sailed it 1,000 miles on what was an adventure of a lifetime for many and then sold it for $5,000. What is wrong with people?

The Erie Canal is an economical ten day trip and a piece of Americana all should experience. The scenery is spectacular, especially with the fall colors when we made the trip just after Labor Day. This waterway was built almost 200 years ago and the history of America is intertwined within. The dozen canal towns are quaint, friendly, and history laden American scenery. You can spend time playing tourist and get a comprehensive American history lesson by reading the many plaques and markers along this inland highway. The locks are manned by helpful, cheerful outdoor types and are nothing to fear… all 35 of them on the 350 miles to the Hudson River. The lock keepers are calm and can’t be flustered no matter how many questions you ask. The next lock will be notified and waiting for you. New York State has this under control and the entire canal experience is a safe and wonderful event.

The only “event” on the entire passage was on Lake Oneida when we were really pushing hard to get across before dark. Just when we’re about to leave the lake and enter the channel between hard and ugly rock tetties in the fast fading daylight, the powerboat behind us ran out of fuel. Girlfriend suggested not seeing them and though tempted, I just had to go back. After all, they were waving so pitifully. I gave them my outboard gas tank, never expecting to see it again and began the careful process of picking our way into Sylvan Beach in the black of night. An hour later, the family of gypsies from the power boat walked up to us with our fuel tank refilled and couldn’t thank us enough. On any body of water, you absolutely must render assistance. It’s the Way.

What’s Next?

We’ve now finished this month-long jaunt down the Erie Canal, New York Harbor, Lady Liberty, Atlantic City, Delaware Bay and the entire headwaters of the Chesapeake and down into Virginia, which is for lovers. As always, we had convinced ourselves it was business and it just couldn’t be avoided.

The owners have long forgiven us for making such a profit so quickly…well, mostly, and as we were cold and tired and exhilarated, we put the little marina up at less than 100 dollars a month and QUIT.

But we’ll be back. As soon as we get bored or excited to see an opportunity to experience something odd or new we’ll be back getting wet and cold and laughing together again.


For More Information:

Sailboat Cowboys

Available on Amazon:


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