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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 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” ]

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Filed under: Boat Travel, Maine, USA

About the Author:

Wade Shepard is the founder and editor of Vagabond Journey. He has been traveling the world since 1999, through 80 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 3165 posts on Vagabond Journey. Contact the author.

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Wade Shepard is currently in: Ulladulla, AustraliaMap