My husband and I had always planned to retire to Martha’s Vineyard. It was a dream we shared. Along with the dream of having a little day sailer in Edgartown Harbor, two million in the bank, our daughter graduating from college in only four years . . . you get my drift. Dreams sometimes stay just that. Dreams.

We retired on Friday, February 13, 1998. February 14th we went to a boat show at the Javits Center in New York City. By the end of the day we were proud owners of a 29.5-foot Hunter sloop that sleeps six, if you're good friends. They really shouldn’t be allowed to sell beer at boat shows. We took lessons from Captain Steve. We learned how to put up the sail, how to tie up and cast off and were in business.

We used to fly small Cessna airplanes. (He flew, I just went along for the ride.) If your hobby is flying, then you have to find places to fly to. The best way to do this (if you only have one day to get there and back) is to use a map and a compass (one of those little tin things you stick a pencil in) and trace a circle around where you keep your plane. Then you look at the map to find interesting destinations. That’s how we found Martha’s Vineyard. We figured boating would be equally exciting. It’s not. Not if you are true fair-weather sailors like we are.  First of all, our top speed is five knots, which will get you to Nantucket or Cape Cod in about five hours if the wind is just right. This rules out going for lunch. Second, the wind is very rarely just right, which means a lot of tacking and gibing, which is a lot of work but not very exciting (unless you’re like my friend Tom, who was taught to never, never gibe. In that case, you’d spend the whole day coming about in little circles, also not very exciting). So we have settled into a routine of sailing to nowhere for a couple of hours and having cocktails at the mooring for a couple of hours. Not exciting, but it suits us just fine.

Frequently, the most challenging part of the trip is navigating the harbor. We never do this under sail, and have only the highest regard for the captains who do. Unfortunately, the captains who do (who pilot everything from 12-foot catboats to 50-foot charter sail boats) turn the harbor into an obstacle course. The rule of the sea is that boats under power give way to boats under sail. Throw the yacht club classes that scoot around like water bugs into the mix, and it can be down right daunting—which brings me to the point of this little tale.

Our first summer in Edgartown Harbor my husband chose the job of casting off the mooring and let me pilot the boat to the outer harbor, where we could safely raise the sails. I became quite good at it, if I do say so myself. Our second season, when he suggested that we alternate jobs so we both learned to do everything, I was a little nervous. I’ve always been a terrible back-seat driver and once drove all the way to Florida so I wouldn’t have to co-pilot my mother (who was known as Lead Foot Lee in her day). Our first few trips in and out went off without a hitch. We must have always timed our trips just right, because the On Time ferry had never even entered our thoughts. One Saturday we had some guests from the mainland who were looking forward to a sail. Our experience in getting people to go sailing with us had always been spotty. I guess we just didn’t look like able seamen. So we were delighted to have company. The sail went smoothly, even though Saturday in Edgartown Harbor is like Five Corners when the ferry unloads. On the way in, with hubby proudly at the wheel and sailboats passing through the ferry lane with impunity, he suddenly realized that the On Time II and On Time III had started to cross and were too close for comfort. We were not the only ones motoring through. Two large sailboats and a cabin cruiser were about to become headlines in the local newspaper. To add insult to injury, the ferry captain blew his horn at us! My husband panicked (not that I wouldn’t have done the same) and turned sharply to starboard, where he almost crashed into another vessel. Fortunately, the other boat also turned sharply to starboard and gave us room to come about. Needless to say, we made it back in one piece (though our friends seemed a tad too happy to set foot back on land). Thanks to the Chappy ferry, we once again have an exciting hobby.

Previously printed in Martha's Vineyard Magazine