The Hurricane Island Outward Bound School, based at the time on its eponymous island off the coast of Maine near Rockland, had for some pedagogical reason moved two of its famous “pulling boats” to Thompson Island, in Boston Harbor, for the winter, and needed them sailed back down east for the summer season. I had eight Dartmouth students in training to become assistant instructors and needing some more time on the water. In addition, the romance of the voyage appealed even more than the practicality. It was the purest of serendipitous coincidences. So on a late April Sunday we drove to Boston from Hanover and started rigging the boats for the trip.

The HIOBS pulling boat (you can google it for photographs) was a marvelous design. A wooden, sprit-rigged cat ketch thirty feet long, broad of beam, and double-bottomed, it was as close to perfectly safe for neophytes to operate as an open boat can be. It carried twelve oars and rowlocks for auxiliary power. As the students stepped the masts and inventoried all the equipment, their learning curves shot almost straight up. Two anchors, masthead lamp, matches and kerosene for the lamp, charts, radar reflector, dividers, box compass, fog horn, life jackets – everything had to be aboard and in its place. We slept on Thompson Island that night, and Monday morning, with a couple of extra staff people, we set sail for Maine.

The drill on a pulling boat was always the same: a bow watch sitting facing forward with his back against the mainmast; a navigator in the stern sheets with the plastic-wrapped relevant chart on his lap; and a helmsman with his eye on either the compass on the deck in front of him or on the next visible goal. If the wind died or was too far ahead – the pulling boats were notorious for poor pointing to windward – out came six or eight oars, and it became a galley. I always found that, grumpy as the lounging crew was at having to start rowing, morale picked right up after only a few minutes of it.

We rowed through the Cape Ann Canal at Gloucester, feeling pretty important as the bascule bridge was raised for us. We sailed inside the Nubble Island light, not noticing till what would have been too late that there were overhead power lines running to it from shore (our masts fit under them). At night we laid the oars lengthwise side by side on the seats, padded them as best we could, and slept half the crew atop them, while the other half ran the boat and kept the log till its watch was up. I remember thinking often, as the water burbled past in the dark, of Huck Finn’s salute to the nautical life: “It’s lovely to live on a raft.”

On an afternoon of light onshore winds our bored, fertile minds began devising ways and materials for getting more sails onto our dawdling craft. With oars for spars, and tarps, towels, and tent flies, we rigged stuns’ls, topsails, jibs, and staysails until both boats – it was a tacit competition– had seventeen out at once. Our speed failed to increase a bit, but it was great rigging experience.

We neared Cape Porpoise a day later, and decided to stop to fill our depleted water jugs. As we approached the town dock, it appeared the whole village was there; they’d seen us far off and thought us lifeboats from a wreck somewhere offshore. I’ll never forget our welcome, from a burly spokeswoman with a huge voice: “Welcome to Cape Pompous!” she shouted. That accent! We were clearly in Maine.

We stopped at Monhegan to replenish our water jugs again, and finally approached Hurricane Island in the middle of the night. The water around it is pretty foul; but if we could keep in the “white sector” of the nearby Heron Neck light, we had clear sailing straight to it. I pointed that out as plainly as I could and went to sleep. I awoke sometime afterward to nervous murmuring and a distant view of a red light. Which way did you vary? I asked. Right or left? No one knew. So we guessed, turned right, got back, luckily, into a clear lane, and headed again straight for the light.

We tied up at last to the Hurricane Island float in the wee hours. No one was about, so we went to sleep in the boats, with the mainsail tented over us to ward off a falling dew. In the morning, for our daily reading, I pulled out Joseph Conrad’s beautiful description in the last paragraphs of “Youth,” of tying to an exotic pier in an open boat at night and waking to his first sight of the East: “It is all in that moment when I opened my young eyes to it....Only a moment; a moment of strength, of romance, of glamor – of youth! A flick of sunshine upon a strange shore, the time to remember, the time for a sigh, and – good-by.”