Sailing in Maine

by Tyler

Back in February of 2009, while Tara and I were preparing to leave the country, our friend Kit was seriously considering quitting her job to enroll in a boat-building apprenticeship. While we were off pursuing our own "crazy" dreams, she abandoned a promising career, completely restructured her life, and sold nearly all of her possessions to move to the seaside town of Rockland, Maine.

It's been a little over six months since Kit started her training at The Apprenticeshop, a school for traditional boat-building and seamanship. Rockland is only a couple hours away from where we're house-sitting, so we took a day trip to the coast, excited to hang out, see the wooden skiff Kit built (so cool), check out the projects she is working on now, and most importantly, go sailing!


Kit couldn't have planned our visit better; we arrived just before the start of the Maine Windjammer Association's annual Parade of Sail, when some of America's oldest working schooners take to the harbor to celebrate maritime history and show off their fine workmanship. Kit's friend Daniel, his sea-savvy daughter Reya, and their friend Melissa were incredibly generous, taking us out for an entire idyllic day on the sparkling blue water.

As a cool breeze whipped the sails against the mast, making a pleasant clang-clang-clanging sound, we lazily criss-crossed around, tacking our way between the various giant boats, waving hello to their captains, all of whom Daniel knew. Meanwhile, we munched on grapes, bread, and cheese, and sipped on many a round of beer, feeling inordinately luxurious as we smiled and sighed, saying "this is the life!"

I love the nautical culture here, from the burly sailors in suspendahs, to the old ladies in coast guard boats screeching "Watch out for tha SCHOOONAHS!" when they're afraid we're getting to close (as if we couldn't see them!!) There's something deeply thrilling about being thrown into a totally foreign environment, replete with vast swaths of new knowledge to absorb.

I have exactly zero sailing experience, but I've entertained many a daydream about circumnavigations on the open sea. It was a humbling experience to be surrounded by indecipherable jargon, and it made me realize just how naive my ideas of "sailing around the world" truly are.

I was a little jealous, witnessing young Reya and her cousin chatting knowledgeably about ships and sailing. I'm sure they will be seasoned captains by the time they're seven or so! Ten, at the very latest.


After many hours of laughing, snacking, and storytelling had elapsed, darkness fell over the harbor, and Daniel sailed Bufflehead to shore. There, we all disembarked to attend a sea shanty concert by the local music legend Gordon Bok. Under the stars, in the fresh salt air, with a brilliant full moon that rose over the shimmering water, we listened to tales of old and songs of the sea.

We forgot our sound recorder, but Tara captured one of the songs using SoundCloud's iPhone app!


Lured by the mythic romance of a seafaring life, lulled by the lapping waves and the sound of a fiddle, I was swept away, dreaming of another epic voyage. Briefly tempted to scrap our plans of building a homestead, I fantasized about dropping everything to learn about boats and sailing so we could set off around the world yet again…

…we won't do that, of course—at least, not right now. Instead, we'll save this experience as the memory of a perfect outing, and learn to sail another day!

Thank you so much, Kit, Daniel, and company!

4 comments

It's long been a dream of Travis to sail around the world - and seeing deserted islands while flying over them, I feel tempted too! Maybe one day!

That last picture is so... dreamy! :) (Sail looking up at the stars)

Posted by Magalie on Wednesday, August 17th, 2011 at 5:17 AM

Hey, cool! I did the week-long "trial" at The Apprenticeshop a couple years ago. Your photos bring back great memories. I was invited to attend, but circumstances ended up dictating otherwise. I still think about it and how cool it would be to spend two years there. (I can't remember if I was reading your blog at the time or not...)

Posted by Greg on Tuesday, August 23rd, 2011 at 11:02 PM

Bufflehead is now not just taking out friends, but now is Bufflehead Sailing Charters, available to hire for your own magnificent experience aboard!

Posted by Daniel Bennett on Wednesday, May 2nd, 2012 at 6:39 PM

That's awesome Daniel :)

If we were looking to charter a sailboat you'd be the first person we'd call. Congratulations and good luck!

Posted by Tyler on Wednesday, May 16th, 2012 at 3:46 PM
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