A voyage to the promised land

Capt. Dan prepares to celebrate after anchoring at Merchants Row. Inset, the author on Isle au Haut with Bailamos in the background. Photo courtesy Jacqueline Llewellyn

December 2021

By Jacqueline Llewellyn
For Points East

Our annual cruise on the 30-foot S2 9.1 Bailamos would take us to Penobscot Bay, in Midcoast Maine, from our home port of Hull, Mass. This would be the northernmost destination in our 10-year cruising history, and my husband, Capt. Dan, and I were excited to see what all the buzz was about, what makes Penobscot Bay a cruiser’s dream. But first we had to get there.

We loaned our house for a month, giving us a nice chunk of time to be out on the water. When we boarded Bailamos, ready to set sail for the 120-mile overnight run to Matinicus Island, we found that our autopilot didn’t work. We had to leave anyway: The house guests and neighbors were waving goodbye.

We’d be sailing for a month – sometimes at night – and we required an autopilot. This was our third, silent, hardworking crewmember. No marine parts dealers on Boston’s South Shore carried what we needed. So we headed for the North Shore. Gloucester is normally an easy day’s sail. But this day the wind was head-on; it was cold, raining and bumpy, and Dan had to man the tiller at all times.

I was below when I heard an explosion, and I thought we’d hit a rock. I ran to the cockpit, PFD in hand.

The engine had stopped dead. In the second it took Dan to put on more rain gear, we’d crashed into a lobster pot. Fortunately, it was a Clorox-bottle buoy, which exploded on impact, debris scattering everywhere. But there was no damage to the boat.

Considering that, earlier in the day, our refrigerator at home decided to die and our house guest’s car had broken down en route, I figured crashing into the lobster pot was “thing number three” of “bad things, come in threes.” I was wrong.

Gloucester is familiar territory. We decided to pull up to a dock-and-dine spot on Rocky Neck. I’m the driver when docking or mooring. Ready for a break, dinner, and a start to our adventure, we weren’t fully prepared when we pulled into the dock. It can be so easy to forget basic boating practices after a year away from cruising – or maybe this is just a poor excuse for a really bad blunder.

I put two fenders out and bow and stern lines, but I was waiting to see if there was room at the dock. There was, and Dan said, “Let’s do it,” and I pulled Bailamos in.

I got close to proper docking distance, but the spring line wasn’t ready, nor the third fender, and the painter of our 16-foot Gloucester Gull dory was still strung out 15 feet astern. The wind, still blowing hard, blew us off the dock, and we missed “the moment.”

I put the boat in reverse to try again. I then ran over our dory’s painter, backing up over the dory, filling it with water, practically sinking it. The prop had cut the line, but Dan quickly grabbed the boathook and caught the stern line before it drifted away.

Mind you, all this was taking place in front of a restaurant, packed with patrons, watching us in disbelief. Thing number four?

A woman ran down to the dock to let us know that we could tie up to her dock next to the restaurant’s dock. But I was too traumatized to try it again.

We set out to anchor in Gloucester’s Inner Harbor. Generally, anchorages have become smaller and smaller, overtaken by larger, more profitable mooring fields. There seemed to be enough room, so we dropped the hook. After Dan dove under the boat to cut off the lines wrapped around the prop from the dory painter disaster, he bailed out the dory. Then we noticed we were drifting too close to another large sailboat.

You tell yourself it’s fine, until the owner of the other vessel tells you what you already know, that you’re too close. There was no other place to drop, so we had to go back to the dock. This time the dory was secured to the port side, lines and fenders were in place, and, with our tails between our legs, we smoothly pulled in like we should have the first time. I almost expected applause. Lesson: Have a plan, be prepared; you’re not parking a car – all things we should have known from Docking 101. Dinner and drinks were fantastic, as was the relief of being safely tied up.

We ordered our autopilot from Defender Marine and had it shipped overnight to our good friend, Capt. Dave Desmond, in Nahant, 40 minutes away by car. A professional lobster fisherman, Dave was coming to Gloucester to get gear, but even if we had already been in Maine, he would have come to our aid. We moved the boat to a town mooring. We didn’t ask permission, or pay – just made a quick tie-up to get the part. We waited for Dave’s call to tell us that our Defender delivery had arrived, and he called us at 11 a.m. We rowed to shore to meet him at the harbormaster building, and he took us to buy diesel fuel while he collected some lobstering gear.

Once we got back to the dock, new autopilot and dory line in hand, we were met by the harbormaster himself – handsome, young and annoyed. He had towed our boat to the town dock. Towed the boat! We were stunned. “The moorings are solidly booked all the time,” he said, “and you can’t just park your boat and leave for an hour. It causes all kinds of confusion.”

We’d been so focused on solving our autopilot problem that we hadn’t really thought things through. The harbormaster could not have been more accommodating, and professional, after we explained our poor decision. “We are here to help you, we’re glad you’re here, but you can’t just pick up a mooring and leave,” he said. “Call us. You can tie up to the dock for free for four hours and get everything you need.” This was news to us. It was time to get our act together.

We made it through the Annisquam River without incident, and Dan said, “Should we just go for it?” Sail to Maine? Matinicus Island? A 110-mile overnight sail to Matinicus Island, where we’d never been before, after an exhausting day, with the stress of bad decision-making. Hmm, let me think: No. We’d done enough for the day – and yesterday, and the day before.

We needed a fresh start. So, four hours later, we arrived at the Isles of Shoals – specifically Star Island, on the New Hampshire/Maine border, about six miles from the Portsmouth, N.H., entrance buoy.

We had a beautiful, quiet evening, and slept well until 1 a.m. when a severe thunder and lightning storm woke us up. I wondered what it would have been like to be caught in a lightning storm in the middle of the night, some 40 miles offshore.

We got a walk in on Star before leaving at 11 a.m. so we wouldn’t arrive at Matinicus at night. We had done overnights before, crossing the Gulf Stream from Miami to Bimini; from the Abacos to Fort Pierce, Fla.; and from Panama to the Galapagos Islands. And Dan had crossed the Pacific from the Galapagos to the Marquesas in French Polynesia. These passages were all in the company of other, larger boats. And the international passages had professional navigators and weather experts on call for advice.

For the 95-mile sail to Matinicus from Star Island, we were on our own, and super excited. It was a fine day, a beam reach, with winds in the low teens. Our new autopilot freed us up to read, make lunch, and decide who would rest, and when, during the night run. We each had a lie-down, but I was too wound-up to sleep. We watched the sun set as we left the shore behind. It was nearly a full moon, and the swells, as expected, had a steady rhythm. We were doing five to six knots – which was exactly what we wanted. We’d figured about 18 hours to get to Matinicus Rock by dawn, just in time to see the celebrated puffins.

I took the first watch at 10 p.m. so Dan could get some sleep. We had one reef in the main, and the genoa was about 75 percent. If the northwest wind picked up, we’d be all set in the dark. It was cold, really cold; and so I was – on July 18 – wearing a long-sleeve tee, windbreaker, fleece vest, foul-weather jacket, hat and wool socks. Using my chartplotter and automatic identification system (AIS), I kept my eye on a 93-foot schooner Tree of Life, heading for Rockland. To keep my energy up, I nibbled on a gigantic Trader Joe’s dark-chocolate bar.

The wind dropped down to nine to 12 knots. Our SOG (speed over ground) was down to four knots, but being alone in the dark, I was not going to let out more sail. I love a night watch – time alone, time to think. It’s an ancient, common practice that few people get to experience.

Well the wind did pick up, into the high teens and then the low 20s, with gusts upwards of 25. We were sailing too fast, and the jib had to be furled, so at 12:15 a.m. I called Dan up, and he was surprised at how much the wind had increased and how rough the seas had become.

We furled the genoa some more, which calmed down the boat, and I made some coffee. It was my turn for some rest, and I was really tired. The bunk was made on the high, windward side, but I was too tired to change it. It was a lumpy, rough ride, and I slept fitfully. I was cold, and I had to hold on to the cushion edge so I wouldn’t fall off onto the cabin sole.

I arose from my warm bunk at 3 a.m., and, for the first time in my sailing life, we were trying to slow the boat down. We were simply going too fast to arrive at Matinicus Rock in some daylight. At this point, we were about 30 miles from the rock, the wind was still in the 20s, and the moon had disappeared behind heavy clouds.

Lobster traps were a hazard again, although less so under sail as our folding prop would not catch the lines. The dodger window was closed against the cold and spray, and there was a light rain as we passed Monhegan Light. A trawler up ahead was lit up like a lighthouse. There is an obvious thrill to sailing at night, but it becomes unnerving in a small boat with so much motion, noise, and no moon or stars – only black water, black sky. The instrument lights were the only things we could see.

Sunrise was at 5:15 a.m., though there was no sun because of the clouds. We hoped the wind would moderate so we could see the puffins. Matinicus Rock is remote, and puffins are small, but we did see the orange beaks and the black and white of their plumage, and they seemed to be everywhere once we knew what to look for.

Matinicus Island was five miles from the rock, and at 5:30 a.m., in a headwind of 20 to 25 knots, and after 20 hours in a rough sea, we briefly regretted making the puffin detour.

Later, rested, we were ecstatic to have seen them. We grabbed a mooring around 6:30 a.m., put $30 in the plastic mayonnaise jar tied to the ball, and shared our gratitude for having arrived at the gateway to our dream cruising ground: Penobscot Bay. We made omelets, more coffee, and then slept till noon.

The rest of the voyage went brilliantly: lots of lobster pots, rocks, ledges and fog, and no more mishaps. The bay offered beautiful anchorages, and breathtaking scenery: truly a cruising sailor’s dream. So, no matter what it takes, do it. Get there; it’s worth it. The magic is real. It is indeed the Promised Land.

United States Coast Guard-licensed Jacqueline Llewellyn sails out of Hull, Mass., on Bailamos, a 30-foot S2 9.1 sloop, built by S2 Yachts of Holland, Mich. She started writing about sailing during a one-year voyage between 2015 and 2016 with her husband, Capt. Dan. Check out bailamosatsea@blogspot.com.