I was lurking around the coast of Maine one summer when I picked my friend James up on a dock in Port Clyde; we pointed JADE west for South Bristol. The air was cool, the winds good, and a gray cloak hung over the sea. It’d been a long time since James and I had sailed together. We’d met at DiMillo’s Marina in Portland’s Old Port, where we’d each been living aboard boats for the first time.
This sail wasn’t for pleasure, though—not entirely. JADE needed work. Of course. I’d tightened the new rigging (that holds the mast up) three times, and each time, after a few days of sailing, the leeward shrouds would slacken in a stiff breeze, and the rear stay was running out of adjustment. I’d hesitantly resigned myself to hauling-out and unstepping the mast at a boatyard. James would sail with me for the day, then I’d continue on solo.
We had a 15 knot easterly, and with a newly tightened rig, we set the whisker pole and cruised at a clean 6 knots, both of us smiling as rain splattered our faces. James kicked back in the cockpit, sipped his coffee, and said, “Feels good to be on the water again. This is the life, if you can swing it.”
I knew what he meant. I’d quit my job on a lobster boat, abandoned the season of digging clams I’d intended to work as an alternative, and set out along the coast to see if this was the life, and if I could swing it. My experience with boat ownership had been a polarizing one, as many are: peaks of great happiness punctuated by pits of deep anxiety. I’d heard said that sailing was either boring or scary, but five years into owning my Tartan 34c, the scariest things thus far had been the amounts of work I’d done.
I’d decided to go all-in for the summer, spend a few months aboard, see if my love for water travel would outweigh the costs of boat ownership.
For James, the decision had been clear. He’d stayed in Portland, living aboard and paying bills at marinas, while I’d fled home down east, where a mooring, free winter storage, and the always-depressed economy provided a semi-affordable boat ownership environment for me. In addition, I've mostly lived in cabins without many of the amenities that most people in America consider necessities.
“I realized that I couldn’t do it,” James said. “I didn’t have the skills, I didn’t have the time, I didn’t have the money.”
I watched him as he spoke. He held the tiller in one hand, a cup of coffee in the other, rainwater running off his chin. He had the ability to learn the skills, for sure, but time and money and desire are different factors. He no longer owned his boat, the old Cheoy Lee 36’. He'd had a classic boat experience with a classic boat--dreams shattered by the overwhelming amounts of time and money and work that the boat demands. And after all of that, he'd had a bad scare with some crazy currents and winds near the famously nasty mouth of the Kennebec River.
Perhaps more importantly, he’d fallen in love with a girl, moved in with her, and after paying for boat storage, finally made the decision to put his boat, Soft, up for sale.
(He didn’t really call his boat Soft. I did. And other friends did. I can’t remember what he’d actually named her. But what a great name.)
A part of me was envious—a part I didn’t want to admit to—as my boat slid over the gray seas, Monhegan Island over my shoulder. My summer of cruising was meant to help a clearcut decision arise in my own mind: put the boat up for sale or make cruising a top priority. Cruising isn’t a poor man’s hobby; it can be a poor man’s life, but not his hobby. So was this the life I wanted?
I had friends who wanted to do nothing but cruise, and so the time and money they put into their boats came without second-guesses; it was a necessity. I loved being on the water, but I also, and equally, loved mountains and rivers—especially those in Montana; and increasingly, the lack of maintenance and costs associated with a tent, a canoe, and a campfire were becoming more and more appealing.
James wiped rainwater from his face and stared at his hands on the tiller.
“Then that big storm came, and I just freaked out. I bought new fenders and new dock lines. I couldn’t stop thinking about the boat, and what I’d do with her, and that storm… it was the worst night of my life.”
He said that he’d put all new lines on Soft. New fenders. He’d tried to check on her. In the marina offices, the owner had told him that the storm was worse than predicted and it was pretty rough out on the docks, so be careful. James tried to get out to his boat, but ended up crawling on all-fours as the waves bucked the docks. He finally turned around. He spent the night in a cold sweat.
The next morning, when things calmed down, he reached Soft. She’d parted a spring line, and at some point in the night, someone had gotten out on the docks and tossed a loop over his sheet winch and tied her off, but the side-to battering had pulled the sheet winch from its mount, splitting the teak coaming. Without the forward spring line, the following seas had pounded her against the dock and chafed a hole in the bow.
“She was a total loss,” James said. “The insurance adjuster came. I was sure they were going to tell me it was my fault, even though I did everything I could. The new fenders were all pounded flat. The new lines chafed off. But they wrote me a check, and the next day I sold the boat for cheap. It went from the absolute worst day off my life to one of the best. A huge weight was lifted off of me.”
Fog had closed in while he talked. Not thick, but enough so that we could no longer see Monhegan Island. Pemaquid Point, somewhere ahead of us, had disappeared too. The wind was picking up, so I went up on the foredeck and took the whisker pole down while he ran the tiller and sheets.
A half hour later, we jibed to make our approach to John’s Bay. I took a turn on the tiller as we cleared Pemaquid, the wind on our stern quarter, coming now at 15 to 20. We held a steady 6.5 knots, running against a knot-plus of tide, and JADE felt perfect. She was a fast boat. Ahead of us, we saw another boat on our same tack, and we were quickly gaining on her.
“This thing sails amazing,” James said.
As we caught up with the other boat, I heard a little voice in the back of my mind asking if I’d be happy if I got a call from the insurance company saying my boat was gone and the check was in the mail; all that stress, all that work gone; but also, all that possibility gone, all those horizons gone. All those moments like this one right here.
JADE’s rigging issue came from the mast step base—the blocking on the keel on which the mast was stepped. The blocking was rotten, and was therefore compressing beneath the pressure exerted on the mast by the rigging. To what extent it was rotten, I could not tell. The base was beneath the floor in the head, and there was no access, not even for a glimpse.
“Good luck with it, Buddy,” James said as we parted ways at the boat yard, obviously happy that he wasn’t the one dealing with boat problems, happy that he was climbing into a warm car with his girlfriend and heading back to an apartment in Portland to get take-out and watch a movie while I sat alone in a wet boat reading a Russian novel.
That evening, I opened a warm beer and sat at the table with a calculator, and after punching in the numbers several times over, I looked around the boat. A couch and a girlfriend and a shower, a hot pizza and a cold beer sounded pretty good as the price for hauling and stepping the mast bounced around in my head.
I began to seriously consider selling my boat. After buying her, I’d abandoned everything else in my life and devoted over six months of more-than-full-time work—and ample cash—to refitting JADE, and other than the current problem, she was in great shape; I’d been through her in and out, and finally had her in the shape I wanted her to be in. Even so, I wasn’t sure that anyone would buy her for what I’d have to sell her for—she’d had some damage caused by an explosion, and no matter how you shake it, the word explosion wouldn’t sit well in a buyer’s stomach. Ledge or rock might not sound so bad, despite the fact that the explosion damage wasn’t anywhere near as bad as plenty of ledge-rock damage I’d seen. Or dock damage. Or boat yard damage.
I’ll figure a fair price, I told myself, then subtract a grand for the explosion, even though I’d fixed the damage, and done so with the help of a professional fiberglass worker and marine surveyor who’d laughed at my anxiety and said, “You think this is damage? This is nothing.”
I flat couldn’t afford the boatyard in South Bristol, so I made a few phone calls, and got ahold of Alan Dugas, the owner of Royal River Yacht in Yarmouth. I trusted Alan; not only had he come aboard my boat years ago and spent a fair amount of time looking her over for me, he’d patiently answered questions as I worked my way through the refit. He said he’d take a look at her for me and help me decide what to do before I committed to hauling out.
Thick fog and rain piled into South Bristol. Swinging on a mooring, I rekindled my determination. I realized that I hadn’t yet allowed JADE to truly stretch her legs, which had been my plan. I’d gunk-holed all over Maine, anchored in some of the area’s idyllic anchorages, but I hadn’t really been at sea with my boat yet, hadn’t covered many real miles, gone any real distances, and I felt like I needed to do that before I decided the fate of my relationship with JADE.
I left for Casco Bay the next morning. The sea was flat calm, the tide against me, and I motored the first two hours, but by the time I was clear of the ledges, Damariscove Island off my starboard rail, a bit of southwest air was piping up. NOAA was only calling for 10 knots, and by the time I had the main hoisted, there was enough wind to set the number 2 genoa.
JADE held at a steady four and half knots, and soon Seguin Island Light came into view. The ocean was a slow rolling swell darkened by the southwest breeze, and I gained another knot of speed. I considered tucking into Seguin for the night, but the wind was beautiful, and as I passed the light house at over 6 knots I realized that I didn’t want to stop in Casco Bay either. Hell, the boatyard prices I was so scared of were comparable to a month's rent for an apartment in Portland.
I wanted to gun for Cape Ann and beyond. Despite the fact that I had dear friends in Portland, and boat repairs I needed to tend to, I wanted to keep going, and that was precisely what I had not done with JADE, and precisely what she was built to do. Without knowing it, I’d set parameters on my cruising grounds: Casco Bay to Roque Island, essentially.
Why not keep going? Because I was scared of future boat projects? Because I missed mountains and friends in Montana?
I cleared Cape Small, where my love for the ocean had started. I thought back to being a kid camping on Hermit Island, fishing for mackerel, watching boats, staring out at the sea. I’d moved to Montana for college and spent 12 years paddling the rivers and guiding in the mountains before returning to the east, and I returned for one reason: to be on the ocean. I’d found a job on a lobster boat, learned to dig clams, and for the past decade had made a living on the water.
Now, seeing the beaches and cliffs of my youth from out there on the ocean, I grinned, one hand on the boom and one on the tiller, the sails full, the past off the stern, the horizon stretching before me. One thing was certain. I’d fix JADE and sail beyond my parameters, and perhaps beyond the need to decide.
I had a few days until I was scheduled to meet with Alan at Royal River Boatyard, so I took the long way around Casco Bay, stopping at Cliff Island for the first night, then to Peak’s Island, where I borrowed a mooring and caught the ferry into Portland’s Old Port. There, I visited friends and stocked up on food.
Two days later, I rode the tide up the river to Yarmouth. Alan and his crew hauled me out and parked the boat in their yard. A heatwave hit, and every day was steaming-hot. It was a stressful, awful week of work in the yard, sweat and fiberglass dust soaking me by 8 each morning. But the yard itself was fantastic, and a stand of old white pines towered on a bench up above the river. I set a borrowed tent there, and used the boatyard’s showers and laundry, and friends from Portland came to visit a few times.
When JADE was back overboard, all fixed up, I made my way back down the river and spent the night off of Chebeague Island.
As I put my sails back on, I became aware of the decision that had manifested itself over the last few days. I looked out across the bay at the silver waters. It was September 1st. My boat was stocked up, and I had nowhere I had to be. I had not bills save for my $40 per month cell phone, so all I had to do was feed myself.
I planned to leave Casco Bay the next morning, and when I did so, I’d have to either head northeast for home, or south for the winter.
I pulled the old worn mainsail up, got the battens in, and furled it. The sun blinked over the horizon. The next morning, both sails flying, I exited Casco Bay, the Bahamas somewhere in the far distance.
