Dream a Little Dream

In the right light, an 11-mile cruise can feel like a Shackleton-worthy adventure.

the author on thier boat
Sitting on Delilah and staring back at our course, I felt like Sir Ernest Shackleton. David Blake Fischer

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When I first got my boat, I imagined heading out to sea on all sorts of heroic adventures. In my dreams, I climb the mast barefoot, tie complicated knots, and sail off into orange sunsets. In my dreams, I’m tall and handsome: a skilled sailor who’s totally unafraid on the ocean.

Then, there’s me.

After 18 months with Delilah , my Cape Dory 25 ,  I’ve barely sailed beyond California’s Santa Monica Bay. I can’t tie perfect bowlines or take hunky, sunset selfies. And, in wind over 15 knots, my heartbeat feels like footsteps behind me.

Thaddeus and the author
My pal Thaddeus and me aboard Delilah. David Blake Fischer

My dreams of cruising haven’t come to fruition yet, but I’m making my way. I’m doing what I can, where I can, and I’m doing it now. For instance, despite our noobishness and busy schedules, some pals and I recently set off on a little micro-adventure. That morning, I threw some snacks and beer in a cooler. I put on a hat and cut an old pair of denim pants into shorts. Then, I looked in the mirror. 

Everyone talks about the cost of sailing, but they never warn you about the fashion risks.

Fishing hat with UV neck-protector? Check. Jorts? Check.

Our loose no-plan-plan was to leave Marina Del Rey mid-morning and beat upwind until we reached Malibu — until we smelled surf wax, saw fancy homes stilted on toothpicks over the sea, or spotted Jason Momoa— and then return home.

And so, at 11 a.m., three little buddy boats ghosted out from behind the marina break wall: Althea, a Harbor 25; Time Traveler, a Capri 18; and my pal Thaddeus and me aboard Delilah.

In a clearing haze, we sailed north past nearby Venice Pier and the warm, sandy beaches of Santa Monica. Then, just as the fog burned off and the coffee ran out, a 15-knot breeze showed up. Next thing you know, we were close-hauled, our three little boats on their ears, screaming at 5 or 6 knots. Warm spray came over Delilah’s cabin top. We don’t have a dodger, but my jorts absorbed seawater like a squeegee.

sailing
We were only 11 miles from home. Essentially, we were locals exploring our own backyard. David Blake Fischer

We spent three hours tacking upwind. When we reached Malibu, we turned a few circles, attempted to anchor, failed, but found a mooring ball. Then, we cracked a celebratory beer.

We were only 11 miles from home. Essentially, we were locals exploring our own backyard. Still, sitting on Delilah and staring back at our course, I felt like Sir Ernest Shackleton.

sailboats
At 11 a.m., three little buddy boats ghosted out from behind the marina break wall: Althea, a Harbor 25; Time Traveler, a Capri 18; and my pal Thaddeus and me aboard Delilah. David Blake Fischer

We sailed home on a broad reach. Along the way, Thaddeus introduced me to the music of Charley Crockett, a Texas blues artist who’s a descendent of Davy Crockett. For the life of me, I couldn’t remember what adventures Davy went on, but what did it matter? Here we were sailing past windswept mountains and cliffs that drop like stars into the sea. Here we were on a small boat, wandering the edge of a big ocean, living our own adventure.

We were back behind the break wall at sunset. Thaddeus and I dropped the mainsail and motored through the main channel as gold light painted the sky and the Wednesday night racers flew wing-on-wing behind us.

No, we hadn’t been offshore; our voyage wasn’t an ocean epic. But it was a photo-worthy finish to an incredible day I’ll not soon forget.

Venice Pier
In a clearing haze, we sailed north past nearby Venice Pier and the warm, sandy beaches of Santa Monica. David Blake Fischer

Maybe you’re a new sailor with lofty cruising goals. Or, maybe you’re an old salt, still sailing local waters. Either way, don’t let big dreams stop you from stepping out on small adventures. 

Let’s face it: We can’t all have cajones like Bernard Moitessier, set off on a quest like Robin Lee Graham, or be the next Davy Crockett. But, if you’ve got a little time and a little sailboat, turns out, that’s all you need.

So whoever you are, wherever you are, grab the boat you’ve got, get out there, and go. Look for small adventures, even in your own backyard, and you’ll find them. 

Or, at the very least, you’ll have a nice pair of jorts.

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David Blake Fischer is a “noob” sailor living in Southern California whose work has appeared in McSweeney’s, BuzzFeed, the Moth, and Good Old Boat. He hasn’t crossed oceans. In fact, he’s only recently crossed the Santa Monica Bay. Follow him as he fumbles out the channel, backwinds his jib and sometimes drags his fenders on Delilah, his Cape Dory 25. Find him on Instagram @sailingdelilah.

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