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How to Enjoy Traveling Long Term

SOSUA, Dominican Republic- Projects and traveling should be synonymous. To do something when traveling that you can build upon with each day that passes — a mission, a purpose, a project — is the first and last steps, in my opinion, to building a full life on the road.

Floating around the world without a tether, occupation, or commitment sounds romantic — and it is for a month or two — but even the greatest of romances often turn stale with age.

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SOSUA, Dominican Republic– Projects and traveling should be synonymous. To do something when traveling that you can build upon with each day that passes — a mission, a purpose, a project — is the first and last steps, in my opinion, to building a full life on the road.

Floating around the world without a tether, occupation, or commitment sounds romantic — and it is for a month or two — but even the greatest of romances often turn stale with age.

It is my impression that humans were made to work, that our minds are structured to invite challenges, solve problems, collect, create, and build. My mother told me this when I was growing up, and refused to get a job until the age of 19.

I have always hated work, but I never minded The Work — the projects and little obsessions that can stimulate and command the attention of a man throughout his days. I never wanted to go to work because I was always much too busy doing my own projects to even consider toiling for someone else — I was much too busy for that. Then I realized that if I did not blend my projects with making money that I would need to go home. I was in Connecticut for some odd reason. I got a job.

I helped unload this boat that was full of concrete out of the need for something to do

It is too easy to let your mind go limp and weak when traveling, it is sometimes difficult to find substance behind simply moving from place to place without reason for long durations of time. To travel without a project is to leave out a basic piece of that a human requires to produce happiness.

I look around at the expats in Sosua, Dominican Republic. They are mainly retired, divorced men from the USA, Canada, and Europe. They sit around on the beach, swim in pools, sit in front of the hotel and chat, they drink a lot of beer, get drunk each night, screw “girlfriends.” They are living the dream, they are in paradise, they seem bored to me.

And boredom is little if not a starving for purpose, a show of need for a project.

I read once that alcoholics are often drawn towards the practice out of an urge to enhance the excitement of life, to elevate the pale of ordinary existence, to strive for the extraordinary. I am not sure, I have never had a pathological taste for liquor, but I think a large portion of alcoholism is a result of boredom. Most alcoholics that I have meet seem to have little else to do.

Working on an archaeology project

I am rarely bored because I have filled my life with projects, I always have something to do. I am a person that enjoys the act of doing, of creating, of building, of focusing. I am a pathological concentrator, the rest of the world is a mere background when I am working on a project. I crave this type of concentration. I am an obsessive character that thrives on working on something for the simple joy of being occupied.

If I do a quick survey of the truly non-depressed people that I have known, I think this quality is held in common. In my opinion, boredom is the great purveyor of depression. Only a truly bored person has time to sit around thinking about how much life sucks.

“People need to be productive!” I remember the scolding words of my mother.

But it was a long road before I learned how to blend being productive with traveling. It took many countries and a few continents of travel before I discovered the importance of The Project.

This discovery is what made me a traveler.


I was recently asked in an interview by my friend Dave from The Longest Way Home about the worst day of my traveling life.

I had to think hard about this, I nearly quoted a guy from Cameroon who once turned to me and seriously asked:

“It is true that people have bad days?”

When I answered that it was so, he thought for a moment and then replied:

“I have never had a bad day.”

A bad day of travel is better than the best day of not traveling — as far as I am concerned. My perception on judging bad days is flawed, as I know that even the worse day of traveling is better for me than having a home, a telephone, social obligations, plans, a schedule that must blend flush with other people’s schedules, an alarm clock ringing each morning — I am living the way that I want to, and simply knowing this has the effect of smoothing out many roads that would otherwise be full of bumps and scree.

But I did not want to provide my friend with this stale answer.

So I thought about it. And I realized that I did have a very bad day once. It was the day that I realized that traveling the world could become boring.

The year was 2002, I was in Patagonia. It was my first go at solo long term travel, but my third time in South America. I think I went three months without having a real conversation. My traveling routine then consisted of walking around for around 10 hours a day, eating bread and cheese sandwiches, and writing in a notebook and reading Chatwin by night.

In essence, I had just spent four months doing about nothing. I had no projects, nothing to do each day but walk around, I was building nothing, accomplishing even less, did not work, did not study — I had the entire world before me but no purpose to give it passion.

I realized that I was bored. This was devastating news to a 21 year old kid who had staked out his life for travel. How could I spend a lifetime doing nothing? I needed something, I needed to revived my childhood love of projects but did not yet know how.

“Working makes people happy,” I was haunted by my mother’s words: could she be right?

I was on the verge of discovering that my travels needed to amount to something more than blowing into towns and blowing back out again like the wind — leaving little trace, collecting even less. I got fed up and went home. I left Patagonia.

Though I soon found myself traveling again — to Ireland, to work. I added a new pattern to my travels — they were no longer just for recreation. I began studying. I began choosing topics of interest, going on location, and learning as much about it as I could. This lead me to my international university studies, and out of this the idea of the traveling project was born.

I now had missions behind my travels. I began traveling places to meet people, to study something, to work, and to write about it. I bit into traveling, I stuffed my mouth full of the world, and realized that I was previously just skimming the surface of the art of traveling where I could have dived to the bottom of the jug.

Traveler studying in Thailand

I began Vagabond Journey.com out of one of my university projects, and this has been the deep dark hole of a project that I have been diving into ever since. Without Vagabond Journey.com there is a good chance that I would not still be traveling. I briefly discussed the possibility of closing shop on the website with my wife a couple of days ago. It was not a serious conversation, I just wanted to see what she would say.

Publishing this site takes a lot of time — I work a full time job like everybody else. I wanted to see if my wife would rejoice if I packed it in and spent my all-day-longs with her and Petra.

She looked at me sharply and quickly stated, “There would be no reason for us to travel anymore if you did that. Just going from place to place gets boring.”

My wife is into the project too.

Chaya’s assessment was acute, it was accurate, she is a person who understands long term travel: traveling around the world for years on end without purpose is a curse — listlessness is the hallmark of a displaced person, Cain’s punishment was to drift about the earth aimlessly. Long term travel without a purpose, a mission, a project can quickly feel like exile. It gets real repetitive just going around the world buying things and having the same inane conversations each day. It is my impression that travelers need projects.

Please believe me, if you are an aspiring traveler with limited monetary resources the routine of travel can get pretty boring pretty quick. Just how many times can you get on a bus, get off a bus, walk to a hotel, stash your bag, walk around, eat in a restaurant, go back to the hotel, leave again, drink a beer at a bar, get asked where you are from, go back to the hotel, go to sleep, wake up, get on a bus, go to another town . . .

A month of this is exciting, two months is to get a thorough routine down pact, anymore and I begin to feel sallow, frail, and weak in the body and in the head. In Patagonia I was feigning for stimulation, I needed to put my idle hands to use, I needed a project. But I did not know this at the time — I thought there was something wrong with me — and I went home.

The less the likelihood of coming out of the other side of a project, the bigger the mountain, the less chance you have of bringing a project to completion the better. I can never complete Vagabond Journey.com. It is too endless, the plot is the entire globe and everything in it. I can take up an interest in virtually anything and it will fit into the theme of this project.

This website has been the fuel, the impetus behind my travels for the past three years. Before this I mixed university projects with archaeology fieldwork. Each day I wake up with a project I have something to do. Each day I can build a little upon that which I did the day before. Each day there is something to accomplish.

Working as a gardener

Every night I go to bed I think for a moment about what I did during the day, I count the pages that I published, I think of travelogue entries that I completed, the travel questions I answered, and I take a quick look at where I stand. This feels good.

I am happy with my days because I work, because I found something to do while traveling. I don’t just make this website because I travel, but I also travel because I make this website. The two endeavors go hand in hand, they are now inseparable, they run flush together: they are the same project.

A working definition of a project

A project is a deep dark bottomless hole that men and women jump down into for the purpose of providing themselves with challenges, stimulation, a purpose, a modus-operadi, a jest at productivity. Projects provide a sense of accomplishment, they can tangibly show the time of your life that you put into them. A project is a monument to yourself: I put X amount of my life’s duration into this thing and here it is. Projects are monuments to your life.

I think of the guy who is building a mountain out of hay bails in the southwest of the USA. He says that he is doing if for God, and it is my impression that he is on to something. The actualization of time spent is often an actualization of life itself.

There are many projects that I think would mold themselves very well with traveling. There is writing, website construction, working jobs, teaching English, taking classes, learning a trade, being taught how to dance, studying a foreign language, practicing an art, self-conditioning your body, climbing mountains, becoming a dive master, volunteering on farms, trading work in hostels for free accommodation, collecting stories, collecting things, studying abroad, investigating history, learning about culture.

The possibilities are endless.

I am often asked by readers what they need to do to prepare for traveling, and, beyond the basics, the best advice I can give them is to find a mission, find something that you are passionate about, something that you are interested in, and discover a way to weave it into your travels, find a project.


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Filed under: Perpetual Travel, Travel Philosophy, Travel Tips

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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  • bodhi March 16, 2010, 2:45 pm

    I don’t know but I think I prefer the model set by the men of labadie village. Better to sit and do nothing but smile and enjoy the view. Different strokes for different folks. I guess the work ethic is pretty ingrained in some folks.

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  • Mike Crosby March 16, 2010, 7:01 pm

    Thanks Wade. Wade, I have a question. I’m finding that I’m responding to your posts frequently. And to be honest, I’m not sure if I’m boring or not. If so, just let me know, and I’ll not comment as often. It won’t hurt my feelings.

    How you phrased your post is brilliant. I’ve wondered that if travel was merely going around talking to people, getting about, etc, what’s so good about it? But defining travel with the purpose of work and growth, it makes so much more damn sense.

    I have a little heating/ac/appliance repair business and for me it’s an absolute blast. In a small way, when I install a heating/ac system, I’m my little own Picasso. It’s fun to have the ability to take something that’s not working and to make it whole.

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    • Bob L March 16, 2010, 8:17 pm

      Don’t stop commenting. The comments are what bring this site together, at least for me. Wade’s writing is great, but the comments convert simple writing into almost a family affair.

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    • Wade | Vagabond Journey.com March 16, 2010, 9:35 pm

      Bob is correct, Mike,

      Your comments are great, and the contributions of ideas, suggestions, critiques, and questions is what makes this travelogue complete. It is just my job to propose an inference, it is yours to let me know if it makes any sense or to make it grow. Your comments are very much appreciated, they help to make this site into what it is. Thank you.

      Bob had a good way to put it, this has become an almost family affair.

      This is part of what I love about it.

      Walk Slow,


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  • david March 17, 2010, 6:26 am

    Hehe. I’ve been aware for quite some time now, that after years of reading your, Andy’s and some other travel blogs, I’m not sure if I’m REALLY inclined towards long term travel. And started questioning the meaningfullness of doing so.

    This post makes it make sense, once again… Guess you can just as well substitute “traveling” in the title with “life”…

    Thanks Wade.

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    • Wade | Vagabond Journey.com March 17, 2010, 10:41 pm

      This is a good way to put it, Dave:

      Traveling is synonymous with life. Thanks for putting the cap on this point, very well put.

      Andy said to me a couple of weeks ago something that went like this:

      “A lot of people read the blog for a while and then stop. I guess they just get sick of reading about real life all the time.”

      It is true, my aim, at least, was to cultivate a somewhat regular, fulfilling, and productive life while traveling. For me, this is not a wild escape, it is life. Though it does, thankfully, get a little wild sometime.



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  • Emery March 21, 2010, 12:10 pm

    In Galapagos, Kurt Vonnegut proposes that the problem with humans as a species is that our brains are just too big. And thus, we need to fill them or distract them in some fashion to ward off boredom and depression. I’m one who tends to fill her time in a variety of productive activities, to the extent that I might consider myself a workaholic. When I take breaks and slow down, I find depression creeping in, so I have to relearn that appreciation of stillness and beauty, like Bohdi talked about with the Haitians in Labadie. Still, all told, I think it’s a healthier compulsion than alcoholism.

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    • Wade | Vagabond Journey.com March 21, 2010, 1:24 pm


      It is my impression that we share a similar passion. Even when doing nothing it seems as if I am doing something — appreciating the fact that I am doing nothing, or enjoying the thoughts of what I want to do. Minds are structured to follow patterns — if you get the wheels spinning fast, then this speed is craved. I don’t believe that people have gears, you move at your pace without alteration.

      I admire people who can move slow — the “Walk Slow” motto is more of a reminder to myself than anybody else — my wife is one whose example should truly be followed. She does not have to do anything all day long to be happy. She has few goals, even less ambitions, but she is happy. She stays occupied with tasks that she enjoys, and does not fret too much about improvement — she is fine how she is and she knows it.

      This is the real special knowledge: to accept your pace and form your life around it. Whether you sit on the beach all day or stay submerged in projects, if you are doing what makes you happy it is all to the same ends.

      Just now my wife went out with Petra and watched a Semana Santa procession, while I stayed in the hotel and published a travelogue entry. We both had perfect mornings.

      Thanks for the comment,


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  • Ryan @ Planting Dollars January 21, 2011, 7:47 am

    I think this is a really great post that anyone doing long term travel should read. Whenever I was traveling just for the sake of seeing things and relaxing on a beach somewhere it wasn’t nearly as fulfilling as the times where I traveled to accomplish something as say, a mission trip. Having a project really gives a greater sense of satisfaction compared to just lounging around.

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  • ross April 16, 2012, 11:33 am

    hi wade, i really enjoyed this article. it hit home more than anything else ive ever read on traveling.

    this is going to be a long comment, but i couldn’t find where to send you an email directly. i’m not particularly internet savvy.

    i’ve been traveling for about 8 years, on and off with various jobs mixed in, and have been struggling with the boredom issue lately. pretty much to the point where i think this is probably my last month of traveling. the monotony of rambling around with no purpose at all is getting mind-numbing. and i have tried many of those things you suggested. i’ve immersed myself in other languages, i’ve learned many sports and been immersed in them as well, i’ve done many work-trade farming jobs, i’ve had jobs where i did legitimately learn a trade, i’ve pushed myself to physical limits from hiking and working, i have hitchhiked and hopped freights all over the US and mexico, i have just recently started bike touring as a form of transportation just for something to do. ive tried to immerse myself in different cultures and learn about different places with little success and i have discovered that i am far too american to really do anything other than live in america and be american. i have never found the satisfaction or fulfillment that i need.

    i couldn’t agree with you more when you say that people need to be productive. i feel the exact same way and nothing ever seemed to be productive enough to suit me. at some point it was like i was creating something to do, just for the sake of, and without any real excitement or passion for what i was doing.

    but anyway, the whole reason for this comment is that i think people who think like you, and like me, are in the minority. i rarely stay in hostels, i prefer more to camp, squat, rent an apartment, a room in someones house, homestays, etc. but since i have been bike touring in chile, whenever i need a break from camping i have discovered that even a cheap hospedaje is pretty expensive and western style hostels can be significantly cheaper. so in my first experiences with these types of hostels i have met people that think so differently, that we are almost like different species.

    mostly groups of europeans, actually all, not most, that travel as a group, do nothing but pay for tourist excursions, get drunk every night, do absolutely nothing productive and are perfectly content! much more than i have ever been trying to be productive. the very few times that i have tried to explain my issues with traveling contentedness, they have for the most part, not understood a word i said. as much as if i was speaking a different language. and some of these groups are traveling more-or-less long term. not as a lifestyle, but close to year long trips. i met a group of 4 australians that were in their 5th month of being in brazil, argentina and chile and they spoke not a word of portuguese or spanish, and yet were perfectly content with their travels. though they spend most of their time in buses and hostels, drinking and watching movies. the only time i saw them leave the hostel was to buy food or drinks.

    so anyway, the point i am making is that i think most people do NOT have a need to be productive. i think that most peoples minds are NOT structured to invite challenges, solve problems, collect, create, and build…only some. it is the rare person that i meet that has the pathological need for a project. when i do meet these people, they are usually entrenched in a project somewhere permanent, usually in the united states. or are frustrated with traveling, like me. i don’t know what is the difference in how the human brain develops, to what its needs are. but i think your perspective, as much as it is dead-on to me, would go straight over the heads of the majority of world travelers.

    sorry for the long rambling comment. it just made me think enough that i had to say something. i enjoy your website, i will continue to read more even if i’m not traveling anymore.

    congratulations on figuring out how to do it!

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    • Wade Shepard April 19, 2012, 10:35 am


      People need to occupy their minds. Being productive and working on projects is how I do this, but most party with friends and seek out entertainment. One of the biggest benefits of solo travel is that it can give you space to think and dissect your life, but, man, too much of this thinking does not leave a person too well off. Given enough time to ponder anybody is going to see holes in their life. It is hard to find something that can continually stimulate you year after year on the road. It is far easier to just travel with friends getting drunk. It is way more difficult to keep on the path engaged in more complex pursuits. Man, you have to find some way to compile your experiences and knowledge in a way that you can visualize it. I just write about whatever I learn and chronicle it on this website and other mediums. This works for me. Without doing this I think it would be difficult for me to really conceptualize and find any value in the past 12 years of my life.

      The way that you’re traveling is infinitely lonely and there is very little regard to be won from your struggles. The hostel crowd doesn’t give two shits about someone who has taken the adventurous road — they are there to get drunk and to screw. You are a traveler. But travel fatigue is normal, and it’s not a problem. The easiest remedy is to go home — in a couple of weeks you would probably be ready to go again. A more difficult and potentially more lasting remedy is to find a partner to travel with. I’ve found girlfriends and wives to be great receptacles for throwing confusing thoughts into — among having many other soothing qualities. My wife doesn’t even respond to 8 out of 10 things I say to her but it feels good to at least have someone to talk at. It’s like Steinbeck’s Travels with Charlie. He traveled around talking to a dog. It is some weird human need to continuously seek out verbal expression and talk to things.

      Hope this helps a little. We’ve all been there.

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  • Pilgrim November 8, 2012, 9:18 am

    Wow, thanks for the the wisdom so freely offered in this article, Wade.

    People consider me the travel-y type because I tend to go on several trips a year, mostly hitchhiking and train hopping for between 2-6 weeks each year, with one 8-month stint overseas under my belt. Most of my life is stilled lived in my home city. I find myself liking the idea of long-term travel, but have found myself to easily feel unproductive and bored (rainy days while being homeless or surfing a working friend’s couch are pure drudgery) within a month or two of travel. The exception was the 8 months in Asia, where I only had 2 months of unstructured, unproductive living, and one of them was spent joyously hitchhiking the backroads of Southern Thailand with my best friend, after 6 months of being apart and simultaneously experiencing times of loneliness away from home, in different countries. The other month was filled with a few awesome CouchSurfing experienced, and a blur of a-town-a-day travel in which I felt invisible and insignificant in the world, because I was always just another foreign traveler no matter where I went. The days I felt best as a lone traveler, were those spent working at a farm, sourcing/staining/talking with market vendors about various instruments and living in community with other Christians. I hate hostels and find most of the people that stumbled in drunk at 2am to be just as obnoxious the next morning. Your assessment of their intentions for travel seem pretty accurate from my experience, and I entirely agree that being productive is what makes travel enjoyable.

    On the other hand, staying putting and working on projects is not travel, as you said, it is merely life. And I find myself loving the travel, the movement, for what it does to the soul. If work is good for the person, I’d argue that the journey is good for the soul. While some sick part of me enjoys the chaos of long flights with multiple length delays and all the camping out on airport floors and sleep deprivation that follows, a 35 hour series of flights across the world is not a journey. Several months spent circumnavigating an ocean, or stopping for a day or two in small towns which lie between distant points A and B is. When you get to experience the life (of the place, of the locals, of your own) in between your origin and your destination, that is a journey. It is life in motion.

    I agree with the point of your article. My question is how do you maintain the motivation to do the projects that keep you happy? I ache for another long trip, but find myself at a point in life where I have little motivation to do projects. Maybe it’s burnout at the U (no, I know that’s part of it), but I feel like at this point heading on a long trip would be an exercise in ultimate loneliness and boredom, at least between here and where friends lie. How much have you had to plan projects before you begin them — or do you just start them as the ideas come?

    For the last year I have been fantasizing about hitch sailing across the Pacific, and took the initiative to get in my first sailing experiences locally this summer. The idea is to hitchhike and hop trains from Canada down through the states, and hopefully through Centro- and Suramerica to get to major sailing ports. In recent years, choosing a destination, usually a city or rural area where I have a welcoming friend, has been enough to keep my motivation up. Now, I do not have known friends at the end of the line, and maybe, no projects in line (other than going the distance I swore I would). Have you any quick ideas for how I might take up projects while making the long journey? I’m a decent writer, but I’d need a purpose better than “check me out” if I were to run a travel blog. I really enjoy sailing and fringes cultures and traditional livelihood cultures and the environment. I had thought of maybe documenting stories of people in distant lands whose livelihoods were being threatened by environmental degradation, but I wonder how to direct myself at an appropriate audience, and how to stand out from other bloggers. I’m also having difficulty finding the type of female partner that wants to put up with these aspirations and confusions on a daily basis. I’m 28, so I’m starting to realize that fun and games are becoming less and less fun and game-like without someone to enjoy it with.

    Anyways, sorry if I seek to much counsel from an ordinary guy. Just some thoughts stirred up by your own words.

    // Pilgrim

    // Quincy

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    • Wade Shepard November 27, 2012, 4:07 am

      Hello Quincy,

      There is nothing wrong with having a long term base and making trips out from there. To keep going in travel means finding a source of income, and while there are many ways to do this — from teaching to selling things in the street — they usually require a sense of passion for the work. So my advice is not to go about this thinking about what would work or won’t work but what it is that you’re passionate about doing and then MAKE it work.

      Don’t burn down bridges before you come to them. Walk up to them and see what it would take to cross them. You mention blogging above, and while this is an INCREDIBLY DIFFICULT way to make money to travel it is possible. I do it, and a few others do as well. If you’re passionate about this then go for it. All of the pieces will come together on the way.

      It’s my impression that you’re from the USA. Teaching English is probably one of the best alternatives that you have to mix times of travel with times of living abroad and making friends. Seriously, this is a clutch way to get around the world and really learn and have deep experiences in the places you’re based in. If you have a 4 year degree it’s easy to find work. If you don’t it’s only slightly more difficult.

      About hitch sailing: don’t do it. Though it’s often romanticized it’s not really something that is done very well in reality. I can’t say how many times I’ve met masses of backpackers in various ports around the world trying to get crewing jobs on boats to get from one place to another. 99% of the time they just end up sitting on shore for a month or two before getting discouraged and giving up. Seriously, regardless of what some may say it’s my impression that this form of transport is not only extremely difficult to do but very annoying as well. To put it mildly, the yachties of the world often don’t tend to be the most reliable of people, and most of them spend most of their times sitting around various ports rather than actually sailing. If you are lucky enough to find one willing to take you on, who is really going somewhere, it’s going to be an opportunity that comes rarely. Add to this the amount of people trying to do this, and you have some pretty low odds.

      Though actual crewing is a way to make some money and get around. But this is work, plain and simple. You don’t decide where you’re going and you do what you’re told. Often, you go between the same places over and over again. While this is a good way to make decent amounts of money pretty quick, it does not carry the same sense of romance that’s often aligned with it.

      Don’t know if you’ve checked this out yet, but I did a series on independent travel work a while back on Vagabond Journey. It’s at: Independent travel work series.

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