I used to turn to sailing for a sense of cosmic balance but fell out of love with the sport in college. Fishing was a cheaper, less time-intensive way to get out on the water. Then, while browsing for an aluminum jon boat, I came across a bright yellow pocket cruiser sailboat that inspired me to take a second swing at blow boating. But it took a fishing tournament to get me back under sail.
A sailboat for a fishing tournament?
Spring: acquiring my project boat
It was a warm May day when I made the last-minute decision to drive six hours to Newport, NC, to see The Diddy—a 1977 Advance Sailboat Sto-A-Way I’d found on Facebook Marketplace. The name had to be a coincidence. If someone were to name a sailboat after disgraced hip-hop artist Sean Combs, surely “Puff Daddy” would be the natural choice.
Everything else about the listing was bewitching. The 16-foot boat had a raised V-berth that drained into the cockpit and a mast that could be stepped by one person from inside the boat. It came with a trailer, a clean title, intact sails, and a four-stroke outboard that started on the first pull. After a few obligatory kicks to the tires, I handed the seller the $2000 I’d saved from my new job at Annapolis Boat Shows.
As it turned out, if I’d kicked the tires any harder, they might have fallen off. On I-95 in Virginia I pulled over and discovered the leaf springs were held together by zip ties and a two-by-four. Also, the license plate and a brake light had fallen off at some point.
Once safely back in Maryland, I discovered more issues. There was a three-foot-long crack underneath the rubrail. The mast step was falling off. What little flotation foam it once possessed had seemingly disintegrated at some point during the Reagan administration. After some reflection, it occurred to me that the seller’s insistence that the sails were “all original” might not have been all that strong of a selling point. In short, it was exactly what I was looking for.
Summer: tinkering with the boat after work
As the days grew longer, I found time after work to tinker with the boat. The Boat Shows let me store it in the compound where the floating docks sit in the off-season. I’d stop by West Marine and the adjacent purveyor of adult beverages to pick up supplies on the way to the boatyard. I’d roll up my sleeves, put on some music or a baseball game, and get to work.
I sealed the cracks with marine-grade silicone, through-mounted the mast step, replaced the ancient blocks, and swapped out the Home Depot special for actual lines. Few people had documented the Sto-A-Way online, so I reverse-engineered the rig using photos, an old brochure, and YouTube videos of the Sweet 16, another Advance model.
While I was making good progress, I was hardly racing to get her on the water. I wasn’t looking for a boat. I wanted a project, and boy did The Diddy deliver. That said, I was excited to take her for her maiden voyage which seemed to be fast approaching.
Fall: new home projects compete with time for boat projects
In July, my partner and I moved into our new home, which meant The Diddy finally had somewhere to live. I’d fixed up the trailer, so the ride over wasn’t all that eventful. Backing it into my driveway took 45 minutes, but at least I got to introduce myself to my concerned neighbors. I got her cleaned up, put the cover on, and in the middle of the night, a tree fell on her.
The damage was minor but enough to delay the first trip out. The days were growing shorter and colder, making time scarce and fiberglass work impossible. On top of that, I now had a house that needed my attention. So, the boat sat under a tarp and collected leaves.
Winter: taking a step back
My earliest memory is exploring the cabin of my uncle’s daysailer on a family trip to Poland. I started lessons when I was 10, raced on Lake Michigan in high school, and spent summers instructing in southern Wisconsin.
There was something spiritually grounding about balancing opposing hydrodynamic forces into ordered motion. Sailing offered a window into the majesty of the Great Lakes and an exercise in self-control. That changed when the skipper I sailed with in high school suffered a pulmonary embolism. She was a truly kind person, and I failed to fit her passing neatly into the balanced world that sailing provided me.
I lost interest in getting out on the water. The Diddy remained covered until October of the following year. I even considered selling her.
Wind-powered fishing
I’ve always wondered why there aren’t more sail-driven fishing boats. People fish from kayaks—why not sailboats? Sailboats may be inefficient, but humans fished from them for thousands of years. And since when do anglers care about efficiency?
Last October, I got to test the idea when Annapolis Boat Shows decided to sponsor the annual Fish For A Cure tournament, which raises money for Luminis Health’s survivorship program. I figured entering a sailboat might earn enough attention to raise a few extra dollars.
I uncovered The Diddy and got to work. I patched the fiberglass, added flotation foam, flush-mounted rod holders beside the tiller, and replaced the lines that had dry-rotted over its interment. The motor was no longer starting, so I removed it entirely.
Tournament day
I splashed the boat at the local public ramp. The wind blew 10 knots from the north with gusts to 20. My plan was to tack out of the inlet and make for the West River to troll for white perch.
I made it about a mile before things started to fall apart. Even with the control lines cranked, the main had a massive belly. Feathering the sail kept the boat from heeling too hard, but the luffing shook two battens loose. The tack of the jib came off the chain plate and began flapping uselessly in the wind. After about an hour, it was time to turn back.
On the return trip, one of the shrouds partially snapped. The bolts holding the winch used to raise the keel sheared off. That wouldn’t have been too much of an issue if we hadn’t run aground. We never even managed to get a line in the water. My crew looked ready to abandon ship and swim home.
I, on the other hand, was thrilled.
I think the messiness of the excursion embodied the best of sailing. It requires you to do two things simultaneously; create order while embracing chaos. It almost shook itself to pieces, but The Diddy proved broadly seaworthy. And while we didn’t manage to catch a fish, we ended up raising a little over $1900 for the tournament.
I’m thinking next year we’ll try to catch a cobia.
By Ryan Gullang
About the Author: Ryan Gullang is a cross-disciplinary watersport enthusiast, freelance writer, and self designated 'Vibe Curator' for Annapolis Boat Shows.
