Winter Harbor wander

Sunrise greeted the crew of Bailamos upon their arrival in Penobscot Bay, Maine, after an overnight passage from Hull, Mass. Photo by Jackie Llewellyn

December 2023

By Jackie Llewellyn

My husband Dan and I had such a trip this summer, a monthlong cruise from our home port in Hull, Mass., to Winter Harbor, Maine. We set out on July 19, at 7:30 a.m., after days of preparing to be out on the water for 30 days. This was more of a chore for us because we race on Wednesday nights, and, thus, the boat is generally stripped to make her as light as possible.

We needed to transform Bailamos, our S2 9.1 sailboat, from a racing vessel – with nothing aboard but PFDs and a spinnaker – to our floating home. We added cushions, bedding, cookware (including a propane tank lashed to the stern rail), a Chinese camp stove we use for cooking seafood out in the cockpit, a charcoal grill, 10 gallons of extra fuel, 65 gallons of water, bug screens, a fan, foul-weather gear, food, wine, rum, charts, cruising guides, bikes – and a rug. Our 15-foot Gloucester Gull rowing dory was our tender.

The plan was to sail overnight for 24 hours, the thought of which was an adrenaline boost weeks before we actually set off. Once we reached Matinicus Island, we’d day-sail only. On a perfect morning, one neighbor, Peggy, was up to see us off, and 20 minutes into the cruise, after passing through Hull Gut, the alternator belt shredded. Not to worry: Dan is a mechanical genius, so while I had enough beautiful food, herbs and wine for our voyage, he always has backups for every mechanical failure. Less than 10 minutes later, we were back at it.

I loved the overnight sail, especially while on watch alone. The ocean swells past Cape Ann were big, and the moonless, starless night was as black as it gets. No shore or vessel lights were visible, and the haze from the Canadian forest fires in Canada made it feel like Bailamos was being swallowed by darkness.

We had incredible navigation systems, AIS (Automatic Identification System), and every device I need to know exactly where we are, where we are headed, boat speed, wind speed and direction, what other vessels are in the vicinity, and how fast they are going. Our third mate, an automatic tiller, kept the boat on course.

When the wind died to 4.9 knots, I didn’t touch a thing. I have learned not to let out more sail late at night to get more speed. We had the full main up, and our 155 genoa was out about 65 percent. I stayed on course and enjoyed the experience. A hot coffee about this time would have been amazing.

Around midnight, I woke Dan for his watch. The wind had picked up to about 17 knots, and the main had to be reefed. Dan harnessed himself in, donned his red LED headlamp, and climbed forward to the mast. I disengaged the auto-tiller and headed into the wind; Dan released the clutch for the main halyard, dropped the main about three feet, and attached the first reefing point. Then he hauled on the main halyard and reefing line to tighten everything up.

We arrived at Matinicus exactly 24 hours after setting off, logging an average speed of about 6 knots, and pulled into Criehaven Harbor to grab a mooring for a couple of hours of sleep. At 9 a.m., in light air, we motor-sailed toward Carvers Harbor, Vinalhaven, and the engine died, having run out of fuel. Dan had misread the gauge. The wind was still light, and I dodged kelp islands, lobster traps and rocks, while Dan filled the tank, bled the air out of the fuel lines, and got us going again.

Carvers Harbor was a real-deal lobstermen’s port – busy, crowded, local – and we searched for a mooring to rent without success. So we decided to take a chance at a mooring on Hurricane Island; they reportedly had six of them, but it was the height of the cruising season and we weren’t optimistic. Lo and behold, we got the last mooring. Thirty-six hours after leaving Hull, our cruise was just beginning; the hardest, longest haul was over, and Penobscot Bay, Mount Desert Island and Frenchman Bay – storied sailing grounds – were in our future. The archipelago of islands offered easy day-sails, protection, interesting anchorages, provisions, Acadia National Park, and August weather. We were feeling super lucky.

Hurricane Island is home to the Hurricane Island Center for Science and Leadership. Here were beautiful hiking trails, an old rock quarry and gorgeous scenery. We had read that we should not talk to the teenagers who are doing their solo campouts as part of the program. We rowed the dory to a Maine island kind of beach with granite slabs and smaller rocks. After exploring the trails and fetching the dory to return to Bailamos, Dan took a hard fall slipping on seaweed, resulting in a bloody elbow but nothing broken. It was the first injury of the trip – not a bad one, but there would be more.

North Haven, a lovely island, was just around the corner, and we knew moorings would be available at J.O. Brown and Son’s Boatyard. We looked forward to riding our folding bikes here. On a morning trip to Burnt Island, off the southeast shore of North Haven, we dropped the anchor, rowed to shore for a hike around the islet, then revisited Vinalhaven, at Seal Bay. Seal was beautiful, quiet, protected, and a perfect place to end the first phase of our trip and plan our courses to new places.

We headed out for Burnt Coat Harbor, at Swans Island, on a clear morning, happy to be open-water sailing again. Ten miles from our destination, we cut the engine and enjoyed the quiet of being under sail alone. Some sailors won’t consider starting the engine, but with miles to go before we get home, motor-sailing is how we get it done – no guilt.

The fog rolled in, and we brought the fog horns on deck, all eyes searching for the Burnt Coat entrance markers. Our cruising guides told us that rental moorings, with mayonnaise jars attached, were available for payment. We found one, but this place seemed small and desolate, and I wanted to leave, obviously not giving it much of a chance. While the harbor does not have amenities for visiting boats, there was a small market. When the fog lifted, the harbor expanded, and a schooner out of Rockland anchored in front of us. Her passengers appeared delighted with the scenery, swimming, the lobsterboat action – and the sunset.

Frenchboro, an hour and a half away, was next. We wanted to hike the trail that runs around the perimeter of the island. Entering the narrow cove, it was easy to find a mooring, row in and pay for it at Lunt’s Dockside Deli, where we grabbed a nice lunch. There was no one on the trail and the views were phenomenal, so it was unfortunate when I injured my foot. I didn’t anticipate really rocky hiking, and wore thin, old sailing shoes. My left foot felt broken or bruised, and I couldn’t step on the ball. I had to put my weight on the heel and walk on the side of my foot, and the foot was too swollen to wear my boat shoes. Dan made a makeshift Ace Bandage out of some elastic material, but it didn’t really help. I’m sure, viewed from a distance, with me only using the side of one of my feet, I must have been quite an interesting sight.

We sailed to Mackerel Cove, back on Swans, and received a tour of the island and some local knowledge from Jennifer, a local realtor. Jennifer dropped us off at the ferry dock, and we rowed back to Bailamos. We had a decision to make. The weather was definitely a bit iffy – a bit windier than we would have liked – but the racers in us prevailed, and we pulled up the anchor and headed northeast for Bass Harbor, on Mount Desert Island.

Soon the sky darkened, and we decided that heading for Bass Harbor was a bad idea. We headed back in the direction from which we’d come, and soon afterward the heavens really opened up, with plenty of wind and thunder, too. We were fine, though, and considered what could have happened had we not turned around.

The days ahead took us to Islesford, Little Cranberry Island, then to Southwest and Northeast harbors. All of this was easy and wonderful. Moorings were no problem, and we enjoyed showers, laundries, provisions, a free MDI explorer bus, scenery, gardens, historic Inns, paths on the ocean, and a local boatbuilding festival and cookout. We could not believe that the crew of Bailamos, without reservations, at the height of the summer, could waltz into all this magic.

We felt like we had reached the end of our northeasterly cruising, but when we saw Frenchman Bay, in all of its glory, from the shore, we decided to go a little farther, to Winter Harbor, which was our original goal, after all.

Winter Harbor was gorgeous, friendly, and our favorite port of the cruise. It is far enough east that we encountered few cruising boats. The ferry and the lobsterboats were tucked away in a different cove, and the fleets of Bullseyes and Knockabouts claimed most of the moorings. We were welcomed at the Winter Harbor Yacht Club, which was exquisite and historic. Here, we could safely leave our bikes, swim in an empty pristine pool up the hill, accept invitations for coffee and muffins, and sign on the support boat for the Herreshoff Cup Race.

We stayed in Winter Harbor to watch the Lobster Boat Races. These events are held in August, all along the coast of Maine. The Winter Harbor races are scheduled to coincide with the annual Winter Harbor Lobster Festival. It was cool to see these working boats put on a show. We heard that the best race was at the end, when the souped up Class-N 40-footers, with 751- to 1,000-horsepower engines, go ripping down the course.

Our goal – Winter Harbor – had been achieved, and the quest had been delightful. I now have dreams of sailing farther Downeast – I’ve heard Roque Island is Shangri-La. Maybe next year.

U.S. Coast Guard-licensed Capt. Jacqueline Llewellyn sails out of Hull, Mass., on Bailamos, a 30-foot S2 9.1 sloop. She started writing about sailing during a one-year voyage between 2015 and 2016 with her husband, Capt. Dan. Check out