Notice anything different about me? Am I glowing? Do I look like I’m in love? If you guessed it’s my boat-iversary, then you nailed it. Yeah, sorry everyone, but I’m totally that guy right now. The annoying, overly-romantic sailor. The dude posting “me-and-my-boat” photos with music by Barry White. The guy saddled up at the bar, telling total strangers how great his sailboat is.
Delilah.
Boat work is not David’s strong suit, but he still makes an effort.
It’s been four years since I took the leap; four years since I stopped dreaming, rented a pickup, and drove 18 hours up the West Coast during a pandemic to buy a Cape Dory 25. I know, it was a long way to go. But it made for a good story. Plus, the boat was a pretty green, from a good owner, and recently refit. I was a happy sailor on day one, and 48 months later I’m still smiling.
That said, with the honeymoon now over, my relationship with my sailboat hasn’t always been wine and roses. Of course, there’ve been epic sails, influencer-level boat photos, and fantastic adventures. But there’s also been needless panic, boneheaded decision making, and parts “repaired” that weren’t actually broken (pro tip: your outboard motor will need gas to start).
Anywho.
I’m mostly bad at boat work, and that’s fine. I don’t sew my own sails or go up the mast. I’m not sponsored by Volvo or a yachty-looking menswear brand (yet). What matters most to me is that I’ve had fun, found friendships, and made some fantastic memories on the water.
And so, with that, here are 10 things I’ve taken away from four years of sailing Delilah. I hope my experience inspires, encourages, or at the very least makes you laugh. And, if none of that happens, leave me a rude note in the comment section!
David and his son, Ezra, on a first father-and-son cruise.
1. Go Slow. No Slower. No, Seriously Way Slower!
In November 2020, I was in a mad rush to get a sailboat. After finding Delilah on Craigslist, I raced 18 hours from Los Angeles to Wenatchee, Washington, bought the boat, then turned around and boomeranged 18 more hours home. Back in LA, I quickly raised the mast, snagged a shroud on the genoa track, and bent a few pricey parts. Of course, I left the dock with no gas in the outboard.
Like hamsters on the wheel, we sailors often don’t recognize we’re in a rush. Instead, we’ve gotta fall off the wheel to slow down. For me, slamming into the dock with my new-to-me boat in my new-to-me slip provided a movie script ending to the sequence. In time, I learned to stop rushing, to slow my movement and my thinking. Then, go even slower. But, hell, that part was easy. My boat’s top speed is 5 knots.
Delilah and David silhouetted in the evening sun in Marina Del Rey, California.
2. There’s Value in Screwing Up.
And thank gawd! After making a string of unforced errors, I had to find the silver lining. Being a new sailor has reminded me that expertise is overrated; being a beginner is actually super cool. Let’s face it: you’ve gotta break furlers, spill varnish, and stub your toe 10 times on the same winch if you’re ever going to learn anything.
Am I right? Bueller?
One of the benefits of being a total newbie has been chatting with riggers, racers, cruisers, and tow-boat captains. All made mistakes. All went through beginner phases. Best advice? Quit worrying. Quit trying to perfect the beginning. Instead, just do the thing.
So, “quit worrying” is next on my to-do list. And, if I screw that up too, well, cheers to me!
3. It’s Not All Pleated Khakis and Tommy Bahama Out There.
I grew up sailing $50 dinghies and hand-me-down boats repaired with kitchen caulk. For a long time, I figured everyone out there on bigger boats was some sort of fancy pants. But I’ve found the opposite to be true. For every white-on-linen yachty out there, there are two pirates beating around on a $1,500 Cal from the 1960s. The sailors I’ve met are more Ralph Waldo Emerson than Ralph Lauren. They’re nature lovers, readers, and adventure seekers. Most are operating small boats on tight budgets and wouldn’t step foot into a yacht club…unless the door’s unlocked, the bathroom’s clean, and the drinks are free. Not that I would know anything about that.
4. You’ve Got Enough Gear.
Delilah is a simple boat with hardly any gadgets, let alone amenities. Here’s a master list of all that’s inside the cabin: lights, Jetboil, depth sounder, radio, Porta Potti. Oh, and there’s a string of battery powered Christmas lights I took from my kiddo’s mini tree and should probably give back.
Radical simplicity is a gift, but it can also send you down rabbit holes. For instance, the night before a weekend cruise, I often catalogue all the gear I don’t have. Think AIS, electric outboard, lithium batteries, headroom. It’s a cool wish list, but out on the water it fades to the background and my mind goes to a simple truth: The boat’s got enough gear. What it doesn’t have makes my life easier. And anyway, your buddy boat already has a barbecue, AIS, and an electric outboard. So, honestly, just poach theirs.
Pondering the brightwork.
5. The Boat Can Handle It, and So Can You.
One of my high points was taking Delilah out in 30 knots, just to see how the boat behaves. That day, I tied two reefs in the main and put every belonging that could fall down on the cabin sole. I clipped my radio to my PFD and I clipped myself to the boat. And guess what? Thirty knots showed up. A half hour later, 30 went to 40. Singlehanding, I tacked my way back and forth through the chaos, behind the breakwall, and safely back to the dock. Stable, solid, with only limited swearing from her captain, my little keelboat was a dream and took it all in stride. I did OK too.
6. Things Could Go Wrong, Or Maybe They’ll Go Right.
For many years, I’ve fancied myself as a sort of amateur therapist. Untrained, albeit; unlicensed, of course. As a newbie sailor, you get to be both doctor and patient. A few feelings I’ve helped my client work through include panic in heavy wind, feelings of failure when breaking parts, fear when anchoring overnight, indecision when planning boat projects, disappointment when they turn out meh. And that’s to say nothing of the stress associated with being a quasi boat-fluencer.
Four years into newbie boat ownership, David is still having fun making new adventures with his first sailboat.
Generally, though, what’s most often killed my vibe is a sort of dull, persistent concern that things will go wrong. What if we have problems on our weekend mini-cruise? What if the anchor drags? Fog rolls in? What if my chainplates fail, the mast falls, insurance rules it a total loss, and I end up on a Catalina 250?
What if? What if? What if?
On a recent adventure with a buddy, we were beam reaching home from Catalina Island, reflecting on these and other concerns. Jordan pointed out that for all of our planning for trouble, we rarely anticipate the good.
What if things go right? What if we have a great weekend?
“It is not the mountain we conquer, but ourselves,” New Zealand mountaineer Sir Edmund Hillary once said. I’m going to remember that quote during my next therapy session with myself. And when sailing with pals, I’m going to recite it out loud in a salty New Zealander accent and pass it off as my own.
7. Racing Has Lessons to Teach.
I’ve got nothing against racing around the cans, competing for a mini-keg, or yelling at total strangers on a boat. But racing really isn’t my thing. Maybe if I was a better sailor I’d be more into it. For now, though, I’m more of a micro-cruiser than a club racer. That said, I’ve learned a bunch from tagging along on the occasional Wednesday night race.
Mind you, I’ve basically just been brought along as ballast. Or, more likely because of my good looks. Regardless, watching racers has taught me what an outhaul does, what a cunningham is, how to push a boat hard and squeeze out an extra half knot when the wind shuts off. Perhaps most importantly, though, I’ve seen how a good skipper can welcome a freshman crewman aboard with humor and grace.
Did I offer anything in return? In terms of sail trim, no. But I did bring along beer.
8. You Don’t Have to Cross Oceans to Find Adventure.
A Pacific crossing sounds cool, but I’ve got two kids, a condo mortgage, and an active amygdala. That said, I do love adventure. Malibu’s Paradise Cove is 17 miles from our marina; Catalina Island is 31 miles, and its green mountains and jaw-dropping vistas make me feel like I’m in Greece.
But most times, I don’t have a whole day or a weekend free. So, I’m learning to find simple ways to turn small sails into bigger adventures. In the summer that means heaving-to and taking a swim. On cold days, it’s cooking in the cockpit. And when no better option exists, it’s always a win to sleep aboard at the marina dock. Yeah, there’s LA light pollution. Yeah, the noise of the city is right there. But, waking up at 2 a.m. and sticking your head out of the hatch to see who’s playing club anthems in the parking lot is a part of the adventure, right?
9. Learn to Roll a Reefer.
The Cape Dory 25 is a strong design but sails on its ear in wind over 15 knots. Thankfully, with the help of YouTube, I learned to reef. Still, going to irons in big wind or high seas to drop the main felt nuts. “This will make the boat way calmer!” I’d holler from the mast as the sails flogged, parts banged, and my wife looked on vaguely concerned. It wasn’t until I saw a how-to video on reefing off the wind that my situation improved.
Nowadays, when the wind builds, I put Delilah on a happy point of sail, traveler down, and ease the main. With the genoa driving, I lower the main halyard, pull down on the luff, and hook the reef cringle onto the hook. I harden the halyard again and take in the reef line. Then, returning to the cockpit, I sheet in the main and—BOOM!—we’re back in business.
Four years ago, that sequence would’ve confused me, but not now. Reefing off the wind is a cinch. The boat’s never out of control. It’s saved my gooseneck (I’m sure), and likely my marriage.
Will I make my own how-to video? About reefing, probably not. Unless it’s at a Grateful Dead show.
The JetBoil is one of Delilah’s fabulous modern conveniences.
10. DIY Where You Can: Trust the Pros to Expedite the Rest.
I look great in a tool belt, but I’m no Mr. Fix-It. Nevertheless, I’ve had to undertake a number of projects to keep my boat afloat. I’ve refreshed the teak toerail, handrails, and cockpit coaming; installed a tiller pilot; redid the teak; made a cockpit table; redid the teak; repainted my nonskid; redid the teak; installed stanchions and lifelines; and, currently, as I write this I’m redoing the teak.
Boat work occasionally has rewards. When it doesn’t, I take the following steps:
a. Spend one month pretending I’m going to do the project myself.
b. Buy a few but not all of the necessary supplies, pretending I’ll use them.
c. Hire someone skilled with their own supplies to save my neck.
This is how I don’t do boat work, and you can too!
I love Delilah, and she’s taught me a lot about sailing, boat ownership, and myself. But, I’ll admit—even on my boat-iversary—sometimes I do fantasize about other sailboats. It starts with Craigslist or eBay, or an awesome outing on someone else’s boat. Next thing you know, you’re swiping at Yacht World like a 20-something on Tinder. It’s not that I’m ungrateful. Delilah is good looking and sails like a dream. But let’s face it: She’s over 50!
In my mind, my future dreamboat is pretty simple. It’ll be 28 feet long with the interior of a 40-footer, have the stability of a schooner and responsiveness of a Sailfish. It’ll have glossy wood that sands itself, an electric battery that will never have to be charged, and the marina will pay me to keep it at their dock.
Is that asking too much?
Of course not.
Every boat’s a compromise. And I’m totally willing to do so, so long as that means getting everything I want in my next sailboat. Until then, it’s me and you Delilah. Here’s to four years!
March 2025
