Sometimes You Simply Need To Go For a 14-Mile-Long, Cape Cod Sunfish Cruise

I’d actually wanted to sail my mighty Sunfish to Nantucket. The plan was to shadow the FIGAWI fleet on its annual booze-cruise to the cobbled streets of Titans-Of-Finance-Land in said mighty Sunfish. But…a last minute trip to NYC (I ran into this guy on the Brooklyn Bridge on my way to my meeting. Isn’t his hat #thebombdotcom)…


…on top of all the other travelling I’ve been doing, plus just being in full-on hammer down mode for months-on-end simply caught up with me this weekend. And honestly, it was kinda breezy on race day, and I was having a hard time beating upwind to the line in front of the HP breakwater in my mighty sunfish without the cockpit filling up with heavy, into-irons-inducing water. And I shot awesome photos from my speed runs that morning but……its a long, and kinda sad story (please note my hand-written plea).

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But in fact, I’d already pulled the plug on my little Sunfish-to-Nantucket caper on the train back from NYC only a few days before. Needless to say, Caroline was both relieved and a bit surprised by my attack of normalcy.


But that hardly meant I was simply going to sit on the couch and eat ice cream at home (at least during the day). Au contrare! The boat was rigged. The sun was out. The water was relatively warm. And I believe that sometimes, you simply need to go for a 14-mile-long, Cape Cod Sunfish Cruise. But I really wasn’t planning to. I’m serious. In fact, it was just like when I was not much older than Sammy and I simply wanted to see what was around the next headland (which is, in fact, pictured just to the left of the flagpole in the photo above).


I just wanted to…Keep…On…Sailing. And that’s what I did. The blustery southwesterly blew itself out and left a dying northerly in its wake–as you can see (I only thought to hit Strava on my way back), perfect for some close reaching around Great Island and beyond.

And I gotta be honest. There were moments during the several glorious hours I was out there sailing in my little boat “seeing what was on the other side of Great Island,” when I’d figured out how to lock off the main sheet with a some sort of bend-type knot, and hold the tiller just right, and get the tell-tails streaming back ever-so-straight, and balance my weight just so as my flat-little boat skimmed over the tiny little ripples that happen when a tiny-little northerly blows through when I said to myself, (out loud but no one was there to hear), “I fucking love this.” And I really meant it.

And you can see by my return course pictured above, I couldn’t quite lay the breakwater on my return trip. But who cares? I banged out a couple tacks and sizzled back into the beach like a cagey ol veteran. But I felt like a little kid. And then, I got on my borrowed sea-foam green beach cruiser, and headed home to see my family.


And you know what? They weren’t there. No note. No text message. Nothing. The house was empty, and silent, and erie. And that scared the crap out of me. Because, you see, as elemental, and necessary, and difficult, and as spiritual I always find sailing around the next unknown headland to be, and as utterly compelled (and sometimes frightened) I am be in the moment of the unknown in almost everything I do, sailing long distances on all sorts of boats, and riding long distances on all sorts of expensive bikes, and pushing so hard that sometimes I get worn down, and…wearing disco pants on the patio on a thursday afternoon…


only makes sense when I have my cute little family to return to. And it was in that brief moment, when they weren’t home and I wasn’t sure where they were that I knew…I’m the luckiest man in the world.

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