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Travel by Sailboat Earn Money Selling in Streets

ZIPOLITE, Mexico- Captain Jim was peddling his handmade soaps on the main street of Zipolite when I found him framed in the view finder of my rolling camera. I was shooting a video about the traveling street vendors here, and as I was taking in the soaps, massage oils, and other cosmetics and curios that [...]

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ZIPOLITE, Mexico- Captain Jim was peddling his handmade soaps on the main street of Zipolite when I found him framed in the view finder of my rolling camera. I was shooting a video about the traveling street vendors here, and as I was taking in the soaps, massage oils, and other cosmetics and curios that Jim had for sale we struck up a conversation. He told me that he was the owner of the wooden sailboat on anchor in the harbor of Puerto Angel. I had been searching for this guy for two weeks, I wanted to go on his boat. I quickly sheathed my camera and got down to finding out who he was and what he was about.

Captain Jim, originally from Iowa, now travels from port to port in his 35 foot sailboat, selling home made soap and cosmetic supplies to make up his daily bean money while taking on paying passengers to meet the remainder of his costs. A better travel strategy I have seldom come upon.

But this article is not just about Jim’s travel strategy, to do this would miss the main lessons that I learned from him. What is truly of essence about this guy is how he seems to approach life, business, and travel. The man is a born success — not the success of the millionaire, but the success of a man who constructed a life for himself out of his own mettle.

Captain Jim’s wooden sailboat in Puerto Angel

Most of the entries in the Independent Travel Work series focus on the whats and hows of starting a micro business to raise funds for travel, this entry focuses on the background philosophy that is needed to make one of these businesses a success.

“This series is about the double dream,” I spoke, “the dream of working for yourself combined with the dream of perpetual travel.”

I was explaining to Jim why I wanted to interview him. He quickly agreed.

As we spoke, Jim wove a tale of one entrepreneurial venture after another. He owned a popular toy store in Ithaca, New York, started up a hot tub rental service, various other small businesses, and then he told me that he use to travel around selling organic crepes. My ears perked up at hearing this. Anyone who has ever bought crepes knows that there is a large gap between their cost of production and retail price. I was beginning to think that Jim really knew what he was doing.

Traveling organic crepe vendor

In their simplest form, crepes are just flour, eggs, water, fruit, other stuffing, and topping. All the ingredients are relatively cheap, and when combined together form a delicious and trendy specialty food that can be sold for many times over its production price. I realized then that I was interviewing someone who could feel out the lay of the land before stepping upon it. With a laugh, I grilled Jim about his crepe business, wanting him to mention the disparity between the overhead cost and retail value. He did, with a sly grin on his face.

For well over a decade, Jim traveled around the USA selling crepes at concerts, fairs, festivals, markets, and other events. He would roll into town, pay up to the health board for a permit, and set up shop. He implied that his stand was usually rocking. Crepes are good, and in the USA there are few places to buy them. Captain Jim’s crepes were also organic, yet another excellent buzz word for business. Eventually, Jim’s traveling crepe business grew to the point where he had numerous employees and a 60 passenger bus.

But he lost this business in a flash. Leaving most of his rig parked outside of his uncle’s home in Seattle, he took a trip for a couple of months. When he returned, he found that his truck and trailer had been towed and confiscated.

“My uncle said I could park it there,” Jim told me about the ordeal, “He had been living there for 20 years so I figured he knew what he was talking about.”

Having complications with reclaiming his possessions, Jim resolved to just buy them again at the impeding auction. A confusion about the date of this auction led to Jim not being present, and his business sold off to another buyer. This was the end of the crepe business.

“What did you do then?” I asked.

Jim just shrugged easily and said, “Well, I’d always wanted to learn how to make soap.”

Traveling soap maker

As quick as that, Uncle Merlin’s Soap was born. Jim transitioned to another project, learned how to make soap and massage oils, and then began traveling around the USA selling these items. Interestingly enough, he named this new business after the uncle who was partially responsible for the extermination of the crepe business.

Of course, Jim made this new business a success. Again, he chose an occupation where the retail prices of his merchandise was exponentially greater than the cost to make it.

“I sold the soap for five times what it costs to make. In Mexico, I still get wholesale price,” he told me. Wholesale price is roughly two and a half times over cost.

Jim said that he pulls in an average of 600 pesos per night of selling in the streets of Zipolite — 50 USD. He later added that, over the holiday season when Zipolite was packed with tourists, he had three consecutive days of making over 1,000 pesos. This is very good money for a street vendor anywhere, especially one that sells handmade soap, massage oils, and funny colored elf hats from Thailand out of a few beat up cardboard boxes.

For sure, Jim was one of the highest grossing street vendor in Zipolite. He sold something different, and people responded. Throughout Mexico and Central America, there are many traveling vendors selling handmade wares in the streets. The problem is that 95% of them sell the exact same things: wire wrapped jewelry, semi-precious stones, beaded work, macrame this and that, friendship bracelets, and a few knit handbags. In this sea of sameness, it is easy to take what these otherwise very talented artisans make as just a part of the commercial landscape.

Somewhere, at some point in recent history, some hippie probably sold a macrame butterfly. The legend of this sale must have spread through the hippie ranks like wild fire, and now lots of people are making and trying to sell these macramé butterflies in the streets of Latin America. They do not seem to be flying off the shelves. While few people are selling what Jim does here, and he brings in the money because of it.

Sailing and living on a boat

Captain Jim

After many years of recreational sailing, four years ago Jim bought a 35 foot wooden sailboat which he immediately made into his home. Upon taken the sailboat down to where he was living in Washington, he moved out of his apartment and right aboard. Each night after packing up in Zipolite, Jim hitchhikes the short distance back to his boat in Puerto Angel where he sleeps.

After hearing very contrary positions over the years about the cost of sailing around the world, I asked Jim if traveling by boat is expensive. He laughed at me as said no way. Again, it was reasserted to me that it is free to anchor a boat just about anywhere in the world. If you stay away from the bourgeois ports and don’t feel the need to park in a dock or a marina, traveling the world by sailboat is cheap: you always have a free bed. Jim told me that on only one occasion in his journey from Washington state to the south of Mexico did he need to pay to anchor out in a harbor. Though the charges for taking a boat in and out of a country’s waters is hit and miss as far as expenses go, it probably beats paying nightly for accommodation. And with auction sites like Grays, buying a boat can be more affordable than you think.

I was now sitting on Jim’s boat bobbing around out in the harbor of Puerto Angel. The boat was not huge, but, at 35 feet, there was adequate room for sailing and living. Inside the cabin, Jim had decked the place out into a full operating home. I sat on one of the benches that ran along the inside of the cabin and admired how much sunlight got in there as the boat had a skylight — a great addition that I am unsure is not on more live aboard sail boats. Jim cooked me a good breakfast in the fully equipped though space conscious kitchen. This boat had a comfortable feel, though, like most all sailboats, the living space is more or less a corridor.

Upon eating a breakfast that Jim cooked, he took me around the ship to show me some of its goodies. Inside, he had a Katadyn pump that converts sea water to drinking water that can be operated with the boat’s engine or by hand. Outside, the boat once had an electricity generator that was both wind and wave powered (now broken). A couple solar panels sat near the cockpit. A GPS antenna rose above on top of the mast. This ship was decked out for long term travel.

Although boat repairs, when needed, are expensive, by taking his home with him, Jim keeps his expenses relatively low — a key element of any successful independent travel business — and he also has enough cargo space to keep the materials and supplies which give him a livelihood on the road. One of the biggest obstacles for a traveling street vendor is answering the following question:

How to carry your merchandise and the supplies needed to make it?

Dan, the traveling silversmith from a previous interview, lives and travels in a van, but most wandering artisans often limit themselves to only dealing in  light weight goods — most defaulting towards jewelry.

Sailing adventures

Sailboat for passengers

Captain Jim also makes money taking on paying passengers. For $825 per month, you can travel, most expenses paid, on his wooden sailboat. There is also a work/ trade option to allow some passengers the option of reducing this cost.

But taking on passengers has also put Jim in some very precarious situations. One passenger intentionally beached his boat. She, apparently, thought that a shipwreck would created the perfect backdrop for romance. Captain Jim did not agree. Another set of paying passengers cleared Jim out in California. They came on board, stayed for a few days, and then stole all the boat’s expensive electronic gear and dinghy. As Jim told me these rather awful stories, the amiable smile did not leave his face. I found this odd — if someone did me in for $10,000 or crashed my ship I would more than likely remain perpetually pissed about it.

Personality advantages

I could sit in the street and sell the greatest things known to man and I would be a pauper. This is just me, my character is not that of a salesman. So much of selling things is contingent upon personality, and Jim can boast this ability. As far as I can tell, it seems as if Jim’s salesmanship is an amalgamation of his natural talkative nature and well calculated banter.  If you sit me in the street selling Jim’s soap, I would close the day broke; put Jim in the picture and he takes home 1,000 pesos.

Part of starting an independent travel business means knowing yourself and what you are good at — identifying your skills and weaknesses — and then building your capabilities in a way that they can win you a living. Not all independent travel businesses can be done successfully by all travelers, the trick is knowing your strengths and contorting them in a way that sells.

Jim is one of those people people. He is talkative, non threatening, friendly. If you stand next to the guy for more than a moment you stand the chance of being there two hours later, deep in conversation. He sells well.

Sailing and selling in the streets conclusion

Jim is a successful person, not someone who found success. There is a big difference. There is a way of approaching life that recognizes the avenues more than than the walls, possibilities rather than obstacles. Knowing that there is always a way around a roadblock is perhaps the climatic step between arriving at a desired destination or going home. Nobody ever found success without some tribulation, and difficulties are often a sign that you are making progress rather than something is wrong.

From the stories that Jim told me about his independent businesses it became clear that he takes dead ends as the impetus for changing directions, not as a directive to stop and give up. I asked Jim what his future holds, and he mentioned that he was considering studying massage — another good travel business.

A traveler must be like a lab rat stuffed into a maze: when they hit one dead end, they must turn around and try another way, onward, onward, until they find the cheese at the end of the labyrinth; they must keep trying new things, doubling back when hitting solid walls, ever going in new directions until they find a what they are after. In a world of infinite possibilities, in a maze of infinite directions, you can never be defeated: as there is always a way through to the other side. Though I must admit that I have met few travelers — few people — who live like this. Captain Jim is one.

If you want to travel the world by sea, making money selling soap in the streets, I am here to tell you that it is possible. This entry about Captain Jim is meant to be an inspiration — Hey, this guy is sailing around the world, working for himself, living the double dream — you can do this too. It is possible to make a good life chasing dreams, all too often the only thing to it is to do it.

Filed under: Boat Travel, Independent Travel Business, Mexico, Work

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3705 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

8 comments… add one

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  • G January 16, 2011, 12:38 pm

    Wade, Great story. All your traveling profession pieces have been good but this really stands out. Sounds like an inspiring fellow, the sort of person we can learn a lot from. I believe any one can learn to be a good salesman or businessman, it just comes easier for some people than others. A sincere smile, enthusiasm, and a desire to relate to people go an awful long ways. Captain Jim obviously has it. G.

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    • Wade | Vagabond Journey.com January 16, 2011, 12:56 pm

      Very true, G,

      With the proper cultivation and time, it is my impression that most people can become good at most things. It is just a matter of staying on the path. Though it is probably a little easier to start with something you show a propensity for first haha. There are tons of paths that can potentially lead towards what you want, and if you try them all you are going to find something that works. It is good to see this this lifestyle acted out in reality from time to time.

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  • mike crosby January 16, 2011, 7:00 pm

    Excellent job Wade. I would think that with the people you meet, at times it must be hard to leave. But then again, if you do run into some of these people later, it must be a wonderful experience. That would be an interesting post–stories of people you met in one part of the world, and met somewhere else.

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    • Wade | Vagabond Journey.com January 16, 2011, 7:21 pm

      This would be an interesting topic, as I do meet up with a few people all around the world. Thanks for recommending it.

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  • Alia February 25, 2011, 6:44 pm

    I know Captain Jim, and you sure did capture him in your story! Thanks for writing about his epic journey (part of it), that was awesome.

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  • august June 20, 2011, 7:28 pm

    Just found this web site… real great advice… great site!! How would I get in touch with the sailor? Would be interested to charter his boat?? Thank you for any help.

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