Heading Down to the Islands on a Sailboat is the Best Story Going…

Notes From Aground
5 min readNov 18, 2020

And So Appropriate in the Age of Social Media, Declinism, and Fake News

I know it’s not real but I thought maybe there’d be a fleeting hint of it

Or at least that’s the way it feels after two weeks at sea, heading down the middle of the Atlantic for the Caribbean on a 50-foot sailboat.

Maybe it was all those videos I watched, the cute couple who saved and bought a sailboat after living on ramen noodles, a vegetable garden, and tap water for several years. That carefully documented dream where everything is so blonde and tanned and cute and perfect.

It’s the lifestyle equivalent of false advertising and yet it just looks so good and no amount of filters or staging can get that blue, that offshore, blue water blue.

Like this picture, I took the last time I was out there…

It was supposed to be warm waters in that barren delight, the breeze as steady and trimmed as the main set on a nice reach from just past Bermuda all the way down. A nice lulling of the bow, the soothing push forward, dipping and rising as you read a book and tuck under the shade in the cockpit, peering over at the vane steering gear every so oft. The hours slowly drift by in the nothingness at once terrifying and profound, the spirit steeped and lifted, a sense that matches the one in your spirit, the limitlessness of the horizon paired with the possibility and daring that builds in your soul and reminds you there’s a sailor, a mariner in your very fibers…

Or maybe a stirring of this memory from from my Below Deck period as a yachtie

No.

Instead, the breeze never let up from a solid 25 knots picking up to 40, usually before the night watch, the sails were shortened, reefed (lest we get blown over.) We sailed as close to the wind, tilted/heeled over; trying to hold a line, lest we end up all the way in French Guyana if the food ran out.

It was an endless port tack straight down to the Windwards, an unending lurch and thrust, steady rolls with every big gust that made every task a fun house adventure, steadying yourself in the head or attempting to prepare even the simplest meal on a sadistic amusement park ride, like a television for toddlers where you put something on the counter only to have it flung off a few seconds later. I could almost hear them all laughing at home by the fourth day. It never let up. It was 12 straight days of 3-meter seas and 6 hour watches and hand steering 1500 nautical miles. #NotCruising #NotLivingYourBestCruisingSaltyLife

And yet I wonder if it really happened?

There was no time for a photo or even a few seconds of panorama video, trembling and splashed, at best a blurry frame of sea and sky dappled with water droplets on a spray-covered lens; nothing worth sharing, just a rotten deviation from the cruising course, the one plotted on so many accounts across so many networks. I don’t think #CruisingFails has quite caught on.

[THERE SHOULD BE A PICTURE RIGHT HERE.]

And as I scroll through my photos, that last pic before we set into the North Atlantic:

Right into a favorite bar room composition: Still Life on a Terrace, Wadadli, Table, Burgees;

It doesn’t really bother me that it’s all some lame sea story or that for social purposes didn’t really happen. If anything, it just makes life that much clearer. It only reminds me of that self I find out there, cut off and wandering, the one without a profile suddenly awoken and at the helm or ready to head up to the bow and move the cars or ready the stay sail or the storm jib, eager and excited.

That feeling of escaping the world ashore for the very world itself, the brutal real that needs no recognition, the delight and terror of the elements, that part of you etched with every squall or line of summer storms back home on the Bay or that low the size of Alaska coming back from Europe where you watched the barometer drop on the hour right into the 900s, that part that corresponds to no picture, no past, no profile.

How do you share that with the world? Are words enough?

Maybe that’s why people get out there. For the story not quite told, the one you cannot quite document but occasionally grasp, the words ever short but the chase unending?

Maybe words are all that’s left in this shrinking world where cultures struggle under Instagramitization and homogenization; where wifi hotspots link every escape, every elsewhere into a digital, unrelenting everywhere.

I’m kind of glad I clicked my phone shut on the first day. It still felt like a choice as we watched the shore sink into the horizon rather than that desperate cloying to the 4G, the 3G, the LTE, and then the last few bars before the boat plowed forward into that rare, unknown place where if you’re lucky you will find yourself and the sea and…

Damn, that sounds good. I wonder if anyone will believe it.

Really wish I could have gotten a snap of that feeling after the first week, looking around on a greyish cool morning; when we hadn’t seen a boat for days, suddenly thinking to myself, man this is actually kind of dangerous even though loads of people go out into this on sailboats and make it back.

Then the sail luffs a bit and you adjust course, shrug it off, and drift back into that place. The one without pictures. The one where that other self escapes the story you tell people and there you are in the barren, rawest of the planet, everything so immediate, so self-evident — and you don’t care what anyone thinks when you finally make it ashore and tie up.

What was it like? Do you follow SV What’s-The-Dreaming-Hey-Here-We Are Now!? Oh, my god tell me all about it…And you just go with it. You just go with it because it’s not entirely false and in some way, you’re glad that the truth of it, of what happened can never be explained but felt in some deep quarter of yourself and re-lived, whenever someone offers you a ride offshore…

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