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Buying a Sailboat to Travel the World by Sea

Travel the World by Sea — Vagabond Family Looking to Buy a Sailboat — “”If I found myself anywhere or amongst people I did not care for, all I had to do was to heave up my anchor and go somewhere else. That’s one of the main advantages of living aboard a boat. When you [...]

Travel the World by Sea — Vagabond Family Looking to Buy a Sailboat —

“”If I found myself anywhere or amongst people I did not care for, all I had to do was to heave up my anchor and go somewhere else. That’s one of the main advantages of living aboard a boat. When you want to go away there’s no packing, no taxis, no tips, no trains and no bother. And you haven’t got to find a place to lay your head when you get to your journey’s end. In a boat you must move on and your sitting room, your kitchen, your bedroom and all your little personal comforts and conveniences move on with you. And when you get to your destination there you are — at Home.”
– The &200 Millionaire

“Keep her pointed right into the setting sun,” spoke the captain as I gingerly manned the helm of his 28 ft crusier.

I maneuvered the tiller on our downwind course as the sails filled out fully without luff. The gentle seas flopped against the hull, the day was cinching itself up into its nighttime sack, and port slowly rose out of a sea the flashed an end of the day triage of oranges, blues, and blacks.

As I steered the ship with a newbies keen attention to detail, I made sure to take peaks outside of my bearing at the kaleidoscopic melee of color, as the day transitioned into night over the sea.

I too, was going through a transition — in life, in mind, and in the always brisk winds of life’s intent. I knew that I would soon be a family man, that the tracks that I left behind would now forever be sure to stay in my wake. The road that I was on could now only go rapidly forward: to the new breezes on the lee side of a mountain that I have never before climbed.

Chaya at the helm

Chaya at the helm

My new wife, Chaya, was sitting in the cockpit at my side. She had one hand places softly on the tiller next to my own, as she also was eager to learn the mechanics of sailing. Our child still squirmed inside of Chaya’s belly, and we were all looking forward at a myriad of paths that stretch ahead of our small family to be.

We would continue traveling, we knew that for certain. How? that question would be answered after we take the next big step: after the baby is born.

Though in this moment, as we sailed back to Maine’s Belfast harbor, we knew that we had strapped on a new pair of boots for a road ahead that would be very much unlike the one that brought us here. New methods would be needed to enable us to continue traveling the world with a baby, a little kid, a teenager, and, eventually, as two old raggedy cottonball heads.

We knew that we were stepping onto a new Road, and that it  would be of a very different terrain. As we manned the helm in tandem, Chaya and I both knew that the new road ahead would be one of wind, waves, open skies, and the gentle splashing of a helm on the open water.

It became clear in that moment that our travels will now be by sea.


“Why don’t you two just get a boat and sail around the world?” spoke our midwife at a consultation meeting a week before.

At the midwife’s words a siren storm of lights went off in my head. Chaya and I looked at each other, and our bright eyes and smiling faces were enough of an indication that this suggestion struck fertile ground with both of us.

“Yeah, we should,” I replied, “It would be good to have a sense of home for the baby, a place that we could always return to every night, as we travel.”

This has always been my dream: to voyage around the world by sea, though it has always been an undertaken that I have put on hold. I always figured that I would get a taste of the watery parts of the globe in my later years.

It was a startling revelation to suddenly realize that I did not have to wait until mid-maturity hit to allow this dream a grasping breath of reality: Chaya and I could buy a sailboat, learn to sail, and live the good life of a wandering family in a floating home.

“Sailboats are selling really cheap now, too,” the midwife added as she tossed out the approximate price range in which we could get a decent cruiser.

$10,000 was the price she reckoned.

I could save $10,000 in a handful of months.

We really could get a sailboat and travel the world by sea RIGHT NOW. In a flash it became apparent that there was no better time to begin sailing. Chaya and I were ready to have a baby that would be born at any day, and the notion of providing our child with a freebooting sort of home sounded real good.

With a boat, my family could have a home WHILE perpetually traveling.

I have no qualms about introducing my child to the world as “homeless” but the prospect of a voyaging home sounded to be a far richer option.

My jaw now hung loose in its hinges.

Why didn’t I think of this before?

It all made too much sense to have not have been discussed before this moment. To travel the world in a small sailboat is The Dream. To do so with a small family is to take this dream to another level.

It is funny how a simple suggestion can fully except itself into life in a mere moment; it is funny how a path can turn 90 degrees in a single flash of clarity.

From the moment the midwife haphazardly uttered the idea for us to travel by sea, the path of my small family was drastically altered. From this moment on, there could be no other way.

Suddenly, the thought of traveling with an infant on multi hour, hot, and crowded buses in Latin America seemed appalling; suddenly, day long flights with a traumatized infant seemed hideous; suddenly, I could not think well of any other way of traveling with my family than by sea.

I was sold. I looked over at Chaya — she was sold, too. All of a sudden, my life changed: the grown in path that I was trodding opened upon a wide open clearing of clarity. There could be no other way.

It is now time to see the watery part of the world. For far too long have I endured the fluff, grit, and rubble of the dirt world. Petra is clearly a beacon that the direction I need to travel is forever seaward.

We currently have $6,000 of the $15,000 that I estimate we need before we can set off to travel the world by sea

We currently have $6,000 of the $15,000 that I estimate we need before we can set off to travel the world by sea

Any contributions or support — whether it is advice, good wishes, spare equipment, or even a donation — is greatly appreciated.

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Filed under: Boat Travel, Maine

About the Author:

Wade Shepard is the founder and editor of Vagabond Journey. He has been traveling the world since 1999, through 83 countries. He is the author of the book, Ghost Cities of China, and contributes to Forbes, The Diplomat, the South China Morning Post, and other publications. has written 3223 posts on Vagabond Journey. Contact the author.

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Wade Shepard is currently in: Krabi, ThailandMap