Murphy never met a boat he didn’t like. I’m not a pessimist, just a realist. Spend enough time around boats, and something is bound to go awry.

Boats are natural magnets for trouble. It starts with the environment — dense fog, rain, too much or too little wind, or rough seas. Problems with boats and gear could include a finicky engine, failed electronics and systems, fouled sails and rigging, or leaks in the hull or deck, to name just a few.

But boaters shouldn’t let Murphy wreck their day. Mishaps should be seen as opportunities for learning and adventure. The best boaters take lemons and make lemonade.

A recent delivery from Rockland to South Freeport gave us several such opportunities as we sharpened our logistics skills and continued to get accustomed to our slightly bigger sailboat.

It all started Friday evening. We needed to get to Rockland, where we had left Imagine the prior Sunday following a weekend of racing. So we hatched a plan to stage Randy’s truck at the Harraseeket Yacht Club, leave my car at the train station in Brunswick, take the Maine Eastern Railroad to Rockland, and sail back. The train was comfortable, the ride scenic, and the staff friendly — the trip is highly recommended. Our weekend was off to a great start.

Saturday morning dawned sunny and calm, so we fired up the diesel and headed southwest. We made good time on a favorable current through Muscle Ridge Channel and decided to take the inside route through Muscongus Bay via Eastern Egg Rock, hoping to see some puffins.

We were powering through a minefield of lobster buoys less than a mile from the puffin colony when Murphy showed up. Just a few seconds of complacency was all it took to run over a buoy and foul the propeller. Efforts to free the line with the boat hook proved futile, and there was just enough chop to make a swim under the boat out of the question. Fortunately, the wind filled in, and we were able to continue the trip under sail.

The breeze kept up as we sailed past a TowBoatUS vessel, but finally died about a half-mile from Boothbay Harbor. So Randy hip-tied the Avon inflatable to the port quarter, fired up the trusty two-horse Mariner outboard, and ferried Imagine to a mooring. By then, it was calm enough to take a swim under the boat, and my able skipper cleared the buoy and line from the prop in short order.

Sunday morning offered the kind of conditions cruising sailors dream of — clear skies with a breeze of around 10 knots at the beam — just perfect for trying out our asymmetrical spinnaker.

For the uninitiated, an asymmetrical spinnaker is typically launched and doused using a big sock. In theory, you hook the top of the sail/sock assembly to a halyard, haul it up, cleat it off, then pull on some strings. The sock magically comes up, the sail fills, and the boat reaches along with zero effort under the colorful parachute-like sail.

Our reality was a bit different. Murphy gave us a rat’s nest of lines that required considerable work before the chute could even be launched. Upon takedown, the sock ripped along its entire length and we ended up with another rat’s nest of line. When Randy takes a knife to lines, you know it’s bad.

We eventually made it back home to South Freeport. As we unloaded our gear — including the spinnaker, torn sock, and what was left of the lines — Murphy greeted us with one more piece of cruel reality. Neither one of us had keys to Randy’s truck. With no one left at the club, we pondered over who we might call for a lift home to get the spare keys. Then I had an idea. The tide would be high in two hours — perfect to take the dinghy all the way upriver to the Mast Landing boat launch, which was a reasonable walk from our house where there was a spare set of keys.

It was a lovely night for a dinghy ride, and it was something we talked about doing for years. We cruised past Bartol Island and Pettengill Farm, enjoying stunning scenery and wildlife along the way.

When things don’t go as planned, you end up with a much better story.

Gail Rice of Freeport and her husband, Randy, race and cruise their Pearson 30 sloop on Casco Bay. Contact her at:

[email protected]