The author’s 25-foot Catalina sits in placid waters at Isle au Haut. At right, the author’s partner John points out landmarks on top of Beehive at Acadia National Park on Mount Desert Island. Below, a parade of sail in Boothbay Harbor.
July 2024
Story and photos by Alison O’Leary
In the first week of the summer sailing cruise last year, my partner John and I dealt with an energetic shark that sank our dinghy, braved Bear Week (ptown.org/calendars/bears) in Provincetown, Mass., logged zero-mile days because of repairs to the dinghy, and capitalized on a zero-wind day by playing cribbage and napping.
Yes, navigating new ports on land was just one of the challenges we encountered during our seagoing adventure from Edgewood Yacht Club, in Cranston, R.I., to Bar Harbor, Maine, in the 25-foot Catalina Esmeralda. And it was certainly never boring. When we embarked, we hadn’t articulated goals, like sharpening sailing skills by navigating unfamiliar waters. We didn’t say out loud that a long trip in a small boat, after just 10 months of dating, would be a test of compatibility. We were just doing it because it seemed like fun. Was this fun?
On Day 9, it was dusk when we approached the mouth of the Piscataqua River, on the Maine/New Hampshire border. I was anxious about the river’s strong outgoing current and the many ledges surrounding our destination, Pepperell Cove’s mooring field, in Kittery. John patiently pointed out the channel buoys, blinking red and green, assuring me that we were heading in the right direction despite the disorienting darkness.
Suddenly, on the far shore of the cove, I recognized range lights I’d learned about in a Power Squadron class. My confidence surged as I lined them up and aimed for that distant mark, trusting that we’d be safe on a mooring soon. It had been a long day of sailing from Gloucester Harbor, around Cape Ann, and north to the river’s mouth.
When we arrived in Kittery, on the north side of the Piscataqua River, I thought, “Well, we made it to Maine; we can go home now,” but John had other ideas. He knew there was a national park and hiking trails in Bar Harbor, so our actual destination – at least another week of adventures away – came into focus.
The Piscataqua had a departing gift for us, a mock firefight between two fast center-console boats that weren’t identified as Coast Guard or Navy. We surmised they were related to the Portsmouth Naval Shipyard nearby. “They must be firing blanks, otherwise we’d be on the bottom by now,” John observed. I couldn’t get out of there fast enough.
We continued to bounce north and east up the coast, from Biddeford Pool to Portland to Cape Small, then Boothbay Harbor to Tenants Harbor across Penobscot Bay to Isle au Haut’s Duck Harbor, where we took a day off to hike the rugged lower island. Its scalloped contours revealed one picturesque cove after another and piles of washed-up fishing debris. And wild raspberries.
Every day was different, some with gentle wind pushing us east-northeast and others with thick fog that dialed down late July’s warm sun to a damp chill. And, yes, the lobster pots are actually as thick as mayflies in Maine. One newspaper article said there could be three million of them, and I believe it. We only hit one, and thanks to having an outboard, John was able to untangle it quickly and keep us moving.
Some of the unexpected pleasures along the way included discovering an out-of- the-way port like Frenchboro, where Lunt’s Dockside Deli was a welcome break from the food in our cooler. We actually sailed for fun one day in Linekin Bay, when my daughter and granddaughter came to visit us in Boothbay Harbor. And, after fixing the shark-damaged dinghy, we were able to explore places like Cape Small Harbor, in Phippsburg, from our anchorage off Hermit Island.
When we stepped from the dinghy to the dock at Bar Harbor, Maine, John and I had navigated 350 miles in about three weeks. We were stoked to do some hiking in Acadia National Park, where the highest peak, Cadillac Mountain, looms above the harbor. Unfortunately, we were among a throng of tourists in this not-so-quaint port. After weeks of sailing, being cheek-by-jowl with so many people quickly wore thin.
Getting to Bar Harbor was easier than we anticipated because we took the prevailing southwest winds for granted. When we turned around to go home, the 350 miles before us threatened to be an upwind slog. And we sailed into some spirited weather. I had confidence in the strength of the Catalina’s construction, but helmed within sight of Maine’s many islands for extra insurance.
We felt salty and experienced, never imagining that the learning would continue, with navigating rivers for a significant part of our return leg.
The first test was in Penobscot Bay. We hoped to sail southwest from Stonington and turn west when we got south of Vinalhaven, ending in Port Clyde by evening. However, the weather threw us a curve. Just when the sailing got fun, we noticed clouds filling in from the west. Looking northwest toward Rockland, we watched a schooner with tanbark sails disappear in a sheet of blue-gray rain. A cloud that looked like a stack of dinner plates loomed ominously over Port Clyde.
We turned south and started the engine for insurance, quickly changing our destination to the shelter of the small island of Matinicus, some 10 miles south of Vinalhaven. I felt like Dorothy in the “Wizard of Oz,” running for a shelter she might not reach in time.
The tall cloudbank collapsed, sending a strong gust of wind our way. It caught us suddenly, heeling the boat until the prop cavitated. Our speed shot from four knots to nine knots briefly, then it was over. The cloud had unspooled across the sky, now looking like a long length of rope stretching from west to east on the horizon. We tucked into Matinicus that night, but our weather education was far from over.
Two days later, we fought to make headway going west to Portland with the wind on our nose and building seas. Our options for passing among the islands closer to land were fraught with hazards: We had paper charts, digital charts and a cruising guide, but we were shy about sailing between Chebeague and Cousins islands.
To get south of Portland we motor-sailed and tacked into the wind. It was frustrating to watch bigger boats, with taller rigs, as they tacked south through the sloppy waves. I took comfort in the words of a liveaboard friend who said, “There’s a lot of motoring in sailing.” As long as we were making progress I tried not to feel discouraged. Faced with a prolonged forecast for bad weather, we opted for a town-owned mooring up the Kennebunk River, which would require sharper-than-ever navigation skills.
The Kennebunk is best remembered as being near to the summer home of President George and First Lady Barbara Bush. Given its pedigree, I imagined it would be much larger than it is, but, in truth, its flow is tidal and its size unimpressive. We held our breath at the entrance, consoled that going upstream had to be better than the sloppy three- to four-foot beam seas that rocked our approach.
The cruising guide advised our piloting along the channel markers; the tide was falling and the edges of the river were quickly appearing, shallow and muddy. Over the next two days, at low tide, we’d wonder if Esmeralda’s keel was in the mud because the boats around us were lying on their sides. The channel is dredged to just eight feet deep, and its width can’t be much more than that.
Leaving the Kennebunk was likewise an exciting experience as we raced to beat the low tide at daybreak, breathing easily only after crossing the final bar. Without wind again, we motored to Isles of Shoals, a few miles off of New Hampshire, enjoying spectral views of historic buildings through dense fog.
Later, the fog lifted, allowing us safe passage to the Merrimack River at Newburyport, Mass., where the current tested the upper limit of the 9.9-horse outboard, and the weekend boat traffic tried our nerves.
The final river of our homeward leg featured Massachusetts’ miniature version of an intracoastal waterway, starting in the Annisquam River. It saves dozens of offshore miles, allowing boaters to shortcut Cape Ann, the head of land containing Rockport and Gloucester – if they’re daring enough. The 4.5-mile Annisquam, on a sunny summer Sunday, is jammed with boaters and sunbathers. Piloting a small sailboat from the north entrance to the Blynman Canal at Gloucester Harbor requires concentration and good timing.
At first the current wasn’t challenging, but the boat traffic was thick as lobster buoys in Maine. The southern portion of the passage has its own challenges, including a railroad bridge with a blind entrance, a busy marina, and a climactic drawbridge/canal exit. Soon we cleared the railroad bridge without issue. Then we saw the drawbridge looming just a half-mile away.
It’s a busy area as traffic between Gloucester Harbor and Cape Ann Marina concentrates in that last leg of the passage, a channelized section called the Blynman Canal. I radioed the keeper to make sure we had time to get through the bridge and was told it would be open for just four more minutes. We were in a narrower-than-ever channel with heavy motorboat traffic. I told John we should stop – somehow – and wait for the next opening, but his mind was made up. We were running for it. I think John’s calculated move sought to challenge the keeper: They wouldn’t close the bridge on us, would they?
The outboard whined in protest as we entered the bridge channel, with the incoming current ripping against us. John wagged the tiller to keep Esmeralda headed straight as our progress slowed to a crawl. I looked up at the people lining the bridge above us, but realized they were not cheering for our success. Like Boston Bruins fans hoping to see a fight, they wanted to see us mess up and slam into the bridge, then get pushed back upstream by the current. Somehow, we squeaked through and emerged into Gloucester harbor. I was the only one clapping.
On our return to Edgewood Yacht Club, on the Providence River, we did an extra-long leg from Peddocks Island, near Hull in Boston Harbor, all the way through the Cape Cod Canal to Onset, in Buzzards Bay. When we realized we’d have a favorable current in the canal, we pushed the extra miles. After five weeks afloat, we really wanted to get home, and we did, both boat and crew in fine shape.
Owning an old boat is nothing if not an invitation to adventure. OK, it also requires juggling a budget for upgrades and moving a bucket around in the cabin to catch drips, but it’s primarily a call to adventure. My 37-year-old Catalina 25 presented the means for the adventurous education that John and I triggered when we cast off the lines last July.
Also tested was our ability to subsist on canned food and what we could keep in a cooler. The boat is equipped with only the bare necessities such as running lights, a VHS radio, and an electronic Garmin chart (not a plotter). John, who is 6’ 3”, made the little vessel 90 percent more comfortable by crafting a frame that transformed the saloon into a queen bed where he could stretch out.
In two years of ownership, I’d sailed Esmeralda from Quincy, Mass., through the Cape Cod Canal for a summer in Buzzards Bay, then moved her to a mooring near Providence, R.I. Rarely was there a day that didn’t bring challenges requiring thoughtful solutions. It was different being the decision-maker and owner; I’d previously raced in Buzzards Bay’s Old Sigh Race Series for several years and co-owned coastal cruisers with my ex-husband. This time, my decisions were consequential, for better or worse.
Before this big summer cruise, my previous learning-by-sailing included a fouled anchor in Plymouth Harbor that played havoc with the plan to make the canal’s east-west current in time; a megayacht’s giant bow wake that broke over the cabin-top in Woods Hole; my first solo coastal trip from New Bedford, Mass., to Jamestown, R.I.; and, with my daughter Grace, braving the ripping current of the Westport River.
As the owner of an older boat, my philosophy has been to learn everything I can, push my limits, and enjoy what life the boat and I still have left. After this adventure, my confidence in my abilities has multiplied. Yet it’s tempered by humility. I met an elderly gentleman who scoffed at our trip, telling me, “In the 1960s my wife and I crossed the Atlantic in a 27-foot boat – without an engine.”
New goal?
Alison O’Leary is an author, public speaker and New England sailor. See www.alisonoleary.com for info and a video of the shark that ate the dinghy.
