Editor’s note: This is the second part of a three-part series in which Bogart Salzberg of Portland chronicles a windsurfing journey from Portland to Bar Harbor after being diagnosed with terminal brain cancer.

Whether I was trespassing or not I still don’t know. The tiny Casco Bay islet where I camped, that first night of my voyage, is unnamed on charts and bears no sign. I had stashed my sailboard and gear behind a fringe of low bushes, just to be safe.

The sneaking lent an air of danger to my proceedings which countered the growing absurdity of my goal: to windsurf to Bar Harbor, more than a hundred miles away, in the next six days. Day one had been a bust, and now the heroism of my story (I have “terminal” brain cancer) seemed fanciful, too.

Nearby a generator roared to life. The floating cabin and decks of an aquaculture operation were anchored a few hundred yards away. Paddling past it, through the hot morning air, I wondered how a life of working on the water would temper my nautical whims.

But I allowed myself this whimsical bit of life, yielding nothing of material for the effort, to prove to myself that I can set my soft hands to hard labor and endure and persevere. My low-tech approach of windsurfing and paddling would be a trial of cunning over means, with which to measure my life.

I reached the “new waters” I craved, out of sight of Portland, by mid-day and then rigged for sailing. Ahead east were ranks of mysterious haze-blue islands. The sea-breeze rose and I began to churn a wake. I had the speed I needed to catch up on my schedule.

But I didn’t have the skill. The thing about windsurfing that makes it simple and affordable also makes it difficult: the mast is not stepped but rather rotates and hinges freely at its base. You have to counterbalance the pull of the sail with your own body weight, through your attachment to the boom, or else be pulled over.

I became more exhausted and frustrated with each failure. I would pull myself up onto the board, pull the sail up out of the water and try again to sheet it into sailing position, but always it swung violently and turned me upwind.

I tried to catch my breath in neutral position, with the sail flagging heavily on the downwind side. It was very difficult to balance the board in the wind-whipped chop, like log-rolling while weightlifting.

I sat on the board and drifted off course into late afternoon. I expected to de-rig and paddle but told myself to “just wait” because winds change. Eventually, the wind calmed into and through a nice sailing range, from “bluster” all the way to “anemic.” But I was already paddling by then, spurred by a desperation to regain the lost miles.

A gravel beach on Bailey Island hosted me that night. Two days down, and I was still on the first of four charts for my route. I was still on the first side of the first chart. But the sky was dense with stars, and the solitude delicious. I wished I could bottle that feeling, a feeling of awe, of savoring the best of what life had left for me.

Poplars quivered in the morning air, the next day, but they proved a tease. The air was light and offered so little thrust that I had no force to counterbalance my weight. I was “holding up the sail” while glassy swells rolled under the board.

Soon a “just right” wind came up from the south and I reached all the way to Cape Small in an hour. Around the cape, the weather-beaten hump of Seguin Island dominated the eastern view, with its short squat lighthouse almost 200 feet above the water.

To my left, wild sandy beaches stretched for miles to Fort Popham and the mouth of the Kennebec River. There I found Percy’s Store, with a sign on the door that seemed made for me:

NO SHIRT

NO SHOES

NO PROBLEM

I ate there, charged my phone, and stayed till they closed. They warned me about drinking on the beach: people would join me. And people did.

I returned to Percy’s for breakfast and saw it fill up in an instant as they opened. But it wasn’t families filling the booths, rather a fraternity of older gentlemen all reading the day’s Press Herald like a book group.

That day’s sailing was no more successful than usual. But it was more final. I had decided over dinner at Percy’s to end the trip, at least for now. I ached to my core. So all the while I crossed Sheepscot Bay in the fog, watched a pod of leaping porpoises in Boothbay and was enchanted by the song of the gong buoy at the mouth of the Damariscotta River, I was sprinting for the finish.

I arranged to meet my wife in South Bristol. I arrived around seven, but a tragic comedy of spotty cell phone reception and lack of a defined meeting place had us knocking on doors and occupying porches until we finally met around ten. I fell into bed around midnight, too tired to regret my failure.

In September I returned, this time with a kayak. The difference was striking. The exhausting struggle to balance myself with the sail was replaced by a single-minded focus on paddling. I set out from Pemaquid Harbor in mid-afternoon, reached Port Clyde around seven and ended up sleeping in a park.

The next day, suddenly confident, I was determined to cross Penobscot Bay. But the sea was thick with fog. I rode along Muscle Ridge, hopping buoy to buoy, and set out from Owls Head to cross the western bay to Fox Islands Thorofare.

VHF channel 16 was chattering almost non-stop with “security calls,” or “securité,” depending on whether you can bear the French pronunciation.

I took a bearing off the chart for Stand-In Point, North Haven, and ranged through the dense field of lobster buoys to counter the navigational effects of wind, waves and currents.

The thorofare was calm and sunny, and long. I only emerged to the eastern bay around sunset, and made most of the crossing to Stonington in the dark, with the help of the Mark Island light.

Approaching the harbor, I was confused to see dim fringes of light on the edge of my wake. There was no moon, nor artificial light nearby. Then I noticed that each paddle stroke churned a glowing green orb: bioluminescence.

I was well satisfied to have crossed Penobscot Bay. Tomorrow I would strike for Bar Harbor, partly because I felt I could make it and partly because I felt I must. The weather was only going to get worse from here on out.

Look for the final part in the September issue of The Working Waterfront.