Boothbay, by gosh!

Photo courtesy Mark Barrett

Midwinter 2021

By Mark Barrett
For Points East

Since they became a cruising couple, Mark and Diana dreamed of sailing to Maine in their own boat from Red Brook Harbor, in Buzzards Bay, to Mount Desert Island, in the Pine Tree State. In this installment, we continue their cruise north and east toward their cherished destination.

Finally, after two long, hot days of motoring, we were going to get some wind. It was not a lot of wind, but it was from a good direction. Outside Portsmouth Harbor, we took the sail cover off, headed up, and hoisted the mainsail. Diana and I had big smiles on our faces as we fell off onto a starboard tack and rolled out the jib. We were going to Maine.

Mojo leaned over gently onto a broad reach and accelerated up to 4.8 knots. Okay, that is not very fast, but at least it was quiet. And it was above our agreed-upon four-knot minimum. Diana could not tolerate sailing any slower than that. “Okay, this is ridiculous,” she would say on those occasions when we were barely ghosting along under sail.

“Hang on, I think it’s going to pick up soon,” I’d usually reply. “I see some wind coming from over there.”

“Yeah, right. You’ve been saying that all day. Start the damned motor before I lose my mind.”

On this particular morning, we’d gotten a late start, 11:50 a.m., because we’d gone into town for a leisurely breakfast. Our destination was Portland, Maine, which, according to the calculation I’d made the night before on our chartplotter, was a distance of 40 miles. At an average speed of 4.8 knots, it should take us about eight and a half hours to get there, arriving just before dark.

Lobster buoys were everywhere now, and although there was not as much danger of snagging one while sailing as there was while motoring, I still kept a good lookout. I was pretty sure that Diana was not going to volunteer to jump into that ice-cold water to free us if we got hung up on one.

We sailed past Cape Neddick, and now we were officially in Maine waters. A few hours later, we passed Cape Porpoise, and, almost on cue, a large pod of the cape’s namesake marine mammals appeared off to port. Hundreds broke the surface, their arched backs glistening in the sunlight as they moved swiftly across our path and off to the northeast.

At some point late in the day, I realized that I’d made a navigational error. The night before, when I’d measured the distance on the chartplotter from Portsmouth to Portland, I’d put the final electronic dot on the end of Cape Elizabeth, and not continued the route around the point of land and up into Portland Harbor. In other words, I had miscalculated the total distance by about six miles.

We had a mooring reservation at the Centerboard Yacht Club (CYC), way up in the inner harbor in South Portland (or SoPo, as the locals call it). We were going to be later than we’d thought, so I called CYC for directions to the mooring, in case nobody was there when we arrived. The young woman who answered the phone, who was also the launch driver, said she was off-duty at 9 p.m. By this time, we’d rolled up the jib and were motorsailing at 5.5 knots, approaching Cape Elizabeth. “Oh, we should be in before that,” I told her, doing some quick calculations in my head. Wrong again.

I was not aware of the strong current around Cape Elizabeth until we were struggling against it. Our speed kept dropping until we were barely making four knots under power. It got dark, and the blinding city lights of Portland in the background obscured all the navigational aids. We could not see a thing, including lobster buoys, which we only spotted after we’d passed them. The five-and-a-half-mile leg from Cape Elizabeth Light past Portland Head Light, and up to the entrance of the harbor seemed to take forever. We were doing what we didn’t want to do: enter an unfamiliar city harbor in the dark.

At 9 p.m., I called CYC and told the launch driver that we were on the way, fighting the current, and she said she’d wait. It took us another 40 minutes to make it to the edge of the CYC mooring field. I hailed her on the VHF, and she was already out there, waiting for us. She led us over to our mooring, pointed to it, and took off. According to the entry in the logbook, it was 9:45 p.m. when we finally dropped the pendant over our bow cleat. “Now do you understand why it’s a good idea to get an early start?” I asked Diana when we were down below, watching an episode of “Ozark” on her computer.

“I get it, I get it,” Diana said. “But it would also help if you actually knew how far we had to go.”

A big plus when cruising the New England coast is that you can connect with acquaintances along the way. I had called my old friend Skip Carbin the day before, telling him we were coming to Portland, and he said he’d meet us early in the morning and take us out to breakfast.

At 7:30 a.m., on Aug. 1, we rode the dinghy into the yacht club to shower before Skip picked us up. The building was locked, and nobody was there, so no showers. Skip arrived, and we greeted each other through a 10-foot-high chain-link fence, the gate of which was locked. There was nothing else to do but throw our bags over and scale the fence like a couple B&E artists, only we were breaking out, not in.

Skip drove us in his hybrid SUV to a hippie restaurant, where we had an organic breakfast in the little backyard of the place. The ground was sloped, and the picnic table we ate on was very slanted, but it didn’t bother us. After four straight days on a sailboat, Diana and I were used to things being slanted.

By the time we got back to the yacht club, the gates were open, the flags were raised, and a new launch driver was on duty. We paid the mooring fee of $35, and I left $20 for the young lady who’d stayed late for us the night before. Diana and I took showers in the little outbuilding. According to the logbook, we were off the mooring and leaving Portland Harbor at 10:15 a.m., bound for Boothbay Harbor.

Sailing conditions were ideal. The wind was out of the southwest at 12 to15 knots, and we were able to go on a beam reach straight for our destination. That is the point of sail that Mojo loves, and we clipped right along at a steady six or 6.5 knots. When the conditions are like that, it is hard to get Diana off the tiller, but at one point she had to turn it over to me, and it was not because she had to use the head.

Diana works from home selling speech-recognition software for a company called Nuance, and most of what she does involves working on the computer or participating in conference calls. As long as she has access to the internet, she can work. Her boss had no idea she was on a sailing trip, and she didn’t see any reason to inform him. Halfway between Portland and Boothbay, she had to get on a call, so she handed me the tiller and went below to get out of the wind. While I steered, I could see her down below, her computer on her lap, talking away to members of her sales team, who were scattered all over the country. What a way to earn a living!

We sailed all the way in, past Tumbler Island at the entrance to Boothbay Harbor, before we dropped the sails and started the motor. Dark rain clouds were gathering behind us, so we donned our foul-weather gear for the first time on the trip. We’d made a reservation for a mooring at Tugboat Inn marina, and it was raining pretty hard by the time we hailed the staff on the VHF. The mooring they assigned us was way out on the edge, near McFarland Island, and it was 5:15 p.m. when we picked up the pendant. We went below and waited out the rain, and when it stopped about a half an hour later, we took the dinghy into the marina and tied up next to a big blue trawler named Ivanhoe.

If it seems like every time Diana and I land in a harbor we head straight to the closest bar, well, it’s true. In this case, it was the Tugboat Inn where we found a couple seats among the locals. The bartender was a friendly, talkative guy, and Diana struck up a conversation with a man drinking dejectedly by himself. It was not long before he was pouring his heart out to her. He’d moved to Boothbay several years earlier, hoping to find “someone special” with whom to spend his life. It was not working out like he’d planned, and he was discouraged and thinking about moving on. Diana told him to hang in there, that he would eventually meet somebody, probably when he least expected it.

“I could only hope to meet a woman of such a high caliber as you,” the man said. “And you, sir,” he went on, “you, too, have a certain physicality.”

To this day, I’ll sometimes tell Diana that she’s a high-caliber woman, and she’ll reply that I have a certain physicality, and we smile at each other. Thank you for that, sad barfly. I hope, wherever you are, you’ve found the woman of your dreams.

We ordered our first lobsters of the trip at the bar, someone started to play the piano, and people got up from the bar to sing along in the Tugboat Inn version of karaoke. A big, burly guy did a rousing rendition of Sinatra’s “My Way,” and I complimented him on his magnificent voice. He was the fire chief in town, and we had a friendly conversation with him – where we were from, and where we were going – and, much to our surprise and delight, he picked up our entire tab. Boothbay was my favorite harbor so far.

After that, we walked up the street and, at an Italian restaurant, had a couple more cocktails and some beef carpaccio. Another thunderstorm cropped up just as we got back to the dinghy. If we’d left 15 minutes earlier, we’d have made it out to Mojo dry, but we got drenched. After we dried ourselves off, we watched one episode of “Ozark” and went to bed.

The next morning, we dinghied into the dock around 8 a.m. to check out Boothbay. We had breakfast sandwiches at a coffee shop before walking around the little village, which was hilly and had an authentic Maine feel to it. Unfortunately, some of the shops were open at that time in the morning. Diana pulled me into one, and immediately found something she absolutely had to have.

It was a rock sculpture. To understand why Diana wanted this thing, you must know that her hobby is collecting heart-shaped rocks she’d find whenever she walked on the beach. “If you have love in your heart, you will find them,” she says.

This sculpture was comprised of 30 to 40 rocks, each the size of a hockey puck, in which the artist had drilled holes and arranged on a wire frame shaped like a heart. The rocks were interspersed with pieces of driftwood and whatnot, and a glass heart hung in the middle. It stood about four feet tall, and the base was a rock the size and shape of a deflated football. The thing weighed a ton. “This would be so perfect in front of the house,” Diana said.

“There’s no way we’re taking that thing on Mojo all the way to Mount Desert Island,” I said. “Where are we going to put it? If we put it in the cabin, and we hit some rough seas . . . forget about it!”

“But we have to take it with us. Do you know how much it would cost to ship that back to the Cape? Probably more than it costs to buy it!” I dragged Diana away from the sculpture and back down the hill to the dock where our dinghy was tied up.

We were off the mooring by 9:30 a.m., bound for Tenants Harbor, about 30 miles away. I was silently congratulating myself on my commonsense, although I was a little surprised how easy it was to convince Diana. She gazed back at Boothbay dejectedly as we pulled out of the harbor. Then she turned to me, smiling and nodding her head. “I know what we’re going to do,” she said. “We’ll stop back here again on our way back and pick it up!”

Part 2 appeared in the October/November 2020 issue. Look for the adventure to continue in a future issue of Points East. Mark Barrett started at the bottom in the boating industry – literally – scraping, washing and painting all sorts of vessels. He currently works as a yacht broker for Cape Yachts in Dartmouth, Mass., and lives in Sandwich, with Diana. They sail Mojo out of Red Brook Harbor, in Buzzards Bay.