≡ Menu

Vagabonds Learning to Sail

Vagabonds Learning to Sail — “It looks as if the bug bit them,” spoke Midwife as she watched my wife Chaya and I man the helm of her partner’s sailboat last weekend. After baiting Chaya and I in with the idea that we should continue our travels by sea, Midwife made good on her catch [...]

Support VBJ’s writing on this blog:

Vagabonds Learning to Sail —

“It looks as if the bug bit them,” spoke Midwife as she watched my wife Chaya and I man the helm of her partner’s sailboat last weekend.

After baiting Chaya and I in with the idea that we should continue our travels by sea, Midwife made good on her catch by inviting us to go out sailing with her.

Midwife's sailboat

Midwife's sailboat

It turned out that we chose our midwife wisely, for not only was she a master of her profession, but her partner is a full fledged sailing aficionado who loves everything about sailing, the sea, and the prospect of living full time on the boat you sail. He also happened to be one of those interesting sorts of characters who carried in his head an encyclopedia of knowledge about the small specifications of life: he is the kind of guy who can name wild mushrooms by their Latin name, knows the patterns of the birds overhead, and knows sailboats and the practice of sailing inside and out.

It was his boat that Chaya and I were tentatively steering. He taught me how to tack towards windward while pulling into a narrow harbor under sail power alone. This live lesson in sail/ wind dynamics put the concept together for me:

As I looked into the wind while bringing around the tiller I was able to feel how sailing worked. I watched the wind’s direction, felt its strength, and observed how it all interacted with the sails. Comparing these observations with my actions at the helm, I was beginning to see the initial glimmers of the cause and effect of sailing.

It was a simple breakthrough, yes, but it was a breakthrough none the less: “Aha, so this is how it all works . . .”

Sailing in Maine

Sailing in Maine

While sitting down in the cabin, the captain soon filled up my rucksack with the “how to sail” books that I have been reading obsessively for the past week, and let me know that if I ever had any questions to just ask him.

This sounded good. Especially as I am now at the point where I have unpeeled the covers off of this mission, and have began compiling a near stockpile of questions — lots of them. Spiderwebs inside of spiderwebs . . . I have now gotten inside the web of this sailing fiasco. I am going to do it.

No, we are going to do it.


Chaya and I sailing

Preparing to travel by sea series

[seriesposts orderby=date order=ASC name=”preparing to travel by sea” ]


The only way I can continue my travels and publishing this blog is by generous contributions from readers. If you can, please subscribe for just $5 per month:


If you like what you just read, please sign up for our newsletter!
* indicates required
Filed under: Boat Travel, Maine, USA

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 3717 posts on Vagabond Journey. Contact the author.

Support VBJ’s writing on this blog:

VBJ is currently in: New York City

7 comments… add one

Leave a Comment

  • :: wife mom maniac :: August 18, 2009, 1:11 am

    If you ever sail up the west Canadian coast do stop into my seaside cafe for crepes and espressos! Sailing is the perfect solution to the vagabond family connundrum!

    Link Reply
  • Bicycle Luke August 18, 2009, 6:08 am

    Hey Wade. Congrats to you both on the new bub. Awesome that you guys are into the plans of the next leg already. Sounds like a fantastic idea that you are pursuing and I hope you come across a nice vessel soon. Exciting reading.


    Link Reply
  • Baron August 18, 2009, 9:06 am

    Wade, sailing is a BLAST !!

    I found the local yacht club offered an “adult learn to sail class” that was taught one Saturday a month and was open to the public. I thought the fee was reasonable at just $75, and that included a basic sailing text book. With that one day of focused instruction I felt comfortable piloting a 28ft craft – in fair weather, and on an inland lake – but still, money well spent.

    After that I gained experience by crewing on other people’s boats in the club races. Nobody cared that I wasn’t a club member.

    Then I bought a 20ft boat for myself. And that’s when it started getting expensive. Turns out a boat really is a hole in the water in which you throw your money.

    Anyway, I became interested in learning what it takes financially to live aboard and sail about the world. It aint cheap. On top of you visa, every country charges something for your little ship to be in their waters, plus marina fees, and continous maintenance.

    It’ll cost much more than living out of a backpack – MUCH. But I would do if I were able. I can’t think of a better way to mosey about.

    Take care, and continue to walk (sail) slow.

    Link Reply
  • Wade | Vagabond Journey.com August 18, 2009, 11:25 am

    Howdy Bicycle Luke,

    Thanks man, maybe you could stash your bicycle on our ship and we could give you a lift someday haha! Keep riding!

    Wife Mom Maniac,

    We will surely stop into your seaside cafe. Crepes and coffee is a good enough incentive to travel out that way! Thanks!


    Wow, I did not know that you sailed. Awesome, maybe I should travel out to you and learn a few things haha. Yeah, I am getting mixed figures on how much it costs to travel by sailboat. In the 60’s and 70’s it seemed to have been an alternative sort of lifestyle for people without much money and so it was pretty cheap . . . now, it seems as if it may be becoming more and more of a rich man’s game. I cannot really tell though, from where I am standing . . . I suppose I am just going to have to try it to really find out. Thanks for the advice!

    Walk Slow,


    Link Reply
  • Baron August 20, 2009, 3:02 pm

    I’d gladly teach you what I know about sailing. But you have to bring your own boat. Probably better off staying with the people in main.

    In other news… Here’s an article that is timely to your cause. It includes more resource links.


    Link Reply
    • Wade | Vagabond Journey.com August 25, 2009, 8:23 pm

      Thanks Baron,

      When I get a boat — which may not be for a little while — I will definitely come and find you!


      Link Reply
  • Jim April 30, 2012, 11:37 am

    What kind of boat is that in the picture? Its beutiful!

    Link Reply