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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 [...]

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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:

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 3716 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

13 comments… add one

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  • The Longest Way Home August 16, 2009, 11:42 pm


    I recently had this very discussion with a guy from oz who’s spent years at see. Old school type if you know what i mean.

    Depending on where you are planning on going. You might want to take into account ‘port’ costs. The guy kept going on about how much it costs him to dock anywhere these days. He was mainly talking about SEA. So i don’t know if its a factor in the Americas too or not. But, just passing on what i know so maybe you can make some enquiries 🙂


    Link Reply
  • roy August 17, 2009, 3:22 am Link Reply
  • anonymous August 17, 2009, 11:32 am

    You might want to check out a guy named tim anderson and instructables.com He’s the king of DIY. A lot of it is nonsense, turning junk into junk. But one project might be of interest. He salvaged a sailboat (that was free), fixed it up and now sails up and down the california coast (using it for parties and entertaining rather than a fulltime lifestyle). There is also the editor of a popular sailing mag (sorry memory fails me on this one as far as names are concerned), he bought an old boat for about $3-4,000 did some minor repairs sailed out of SF Bay with his ladyfriend and 4 years later is now in the south pacific around celebes I believe. He claims anyone can do it if they’re inclined. My point is it’s like Frank said in Vagabond Journey, people imagine it requires far more money than it really does. If you’re serious about this I would bet the $6500 you already have would be more than adequate as long as your willing to supply the labor yourself and not contract out the work needed to outfit a boat for a long journey.

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  • Wade | Vagabond Journey.com August 17, 2009, 10:26 pm

    Thanks Dave, for the suggestion. I will keep this in mind.

    Roy, this site was good. I just read through it now. Thanks!

    Anonymous, yes, I agree, you can do just about anything if you really want to do it regardless of funding. I believe that I can pick up a good boat for around $8,000 and suit it out myself for a couple grand more. Looking into things now, I will keep posting everything on here. Thanks also for the encouragement.


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  • Sam Haley September 4, 2009, 8:47 am

    It was a dream of my childhood to travel the World by sea. Unfortunately it hasn’t been transformed into reality yet.

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  • Dublin Hotels September 4, 2009, 10:23 am

    It may seem to be a good idea to buy sailboat and travel by sea. Nevertheless it is not so easy as it seems to be from the beginning. I tried it once and will never do again.

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  • Dave September 18, 2009, 4:11 pm

    I think all dreams are more difficult to make into a reality than we would think but persistance is the key. I am also planning to travel by sailboat and it seems as if there are a lot of people who,for various reasons, tell you this would be a mistake. I have not yet met anyone who is doing it, that regrets what they are doing. I think if you give it a fair effort (I am going to give it no less than a year from the time I leave on the journey) you will be able to make your own mind up as to whether it is what you want to do. I suggest hanging out in the same places as boaties who are doing it and get advice from them. Most people who are doing something you are interested in are more than willing to not only give you advice but to tell you how they did it. By the middle of this winter I am hoping to be doing my refit and by next spring I hope to be on the water. I am new to this just as you are and if you would like, I am willing to share what I learn as I go. If you lived in the right area and are handy with tools I could even use a little help with my refit.(I pay cash) I am retired from a back injury and I will be needing some help with certain things,I have the knowledge, I am just limited with what I am able to do sometimes. Best of luck, Dave

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    • Wade | Vagabond Journey.com September 20, 2009, 6:12 pm

      Right on Dave,

      I would love to come and help you on your boat. Where are you located? I am in Arizona now, but will probably be moving on to another location within the month.

      Feel free to email me at vagabondsong@gmail.com

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  • Chris September 29, 2009, 12:22 pm

    Hey Wade,

    I would be careful in getting too small a boat if your planning on doing intercontinental travel with a baby/toddler. The smaller the boat, the rougher the ride, and the less stable the vessel. Make sure that you and your toddler can handle being in a very small boat in very rough seas, before you buy. Otherwise, you could be coming closer to endangering your wellbeing than you feel comfortable with your baby. Hold out for something 36 ft or above if possible, and many even consider that a bit small. Try for closer to 39+. Get the largest boat that you can single-hand and afford. Also, its much easier to fall off of small boats, and if you do in the open sea when your wife isn’t paying attention or is sleeping, forget about it.

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  • John Trudeau October 8, 2009, 8:51 pm

    I was wondering is there any brand of sailboat that you prefer or better suited for long distance travel?

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  • Dustin March 6, 2010, 6:00 pm

    Ah good ol’ Arizona, now if it only had an ocean! I really enjoyed all of your post. Just reading them made me want to head to the nearest harbor to find a boat to crew. It has been a dream of mine to travel the world solo by sail for as long as I can remember. Once my commitment to the Navy is fulfilled I plan on heading out for who knows how long. Right now I’m waiting for my ship out date. But once I get assigned a base my goal is to build my own boat and save my money. Best of luck to you all!

    P.S. Dave I’m in the Upland area of so-cal till June if your nearby and still looking for the help I’d be happy to give a hand. I’m edger to learn all I can. Email: dustintkd@hotmail.com


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  • Chris April 4, 2011, 7:14 pm

    Check out James Wharram’s boats, they are perfect for what you want, his whole mindset is right up your alley, they are great boats with home builders in mind. I’ve been a professional captain my whole life so I know what I’m saying. You will love them.

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    • Wade | Vagabond Journey.com April 7, 2011, 3:59 pm

      This would be great, if I felt confident enough to build my own boat (or if my wife would have confidence enough to ride in a boat that I built haha).

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