Nantucket Memories: Visiting as a Writer is More Fun than as a Salesman

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We are heading out to a place 29 miles at sea this weekend. The faraway island of Nantucket. I once traveled to this place ten times every year, pursuing sales from companies who made their fortunes during a slender window of commerce–from July 4 til Columbus Day.

I’d fly there on Cape Air…and in the tiny 6-seater Beechcrafts, some times I’d get the front seat, right next to the pilot. You can see the entire shape of this small 10-mile long island from the air. Landing was always a thrill, and then I would set up my little clothing shop in the Dolphin Guest House (now a huge private residence) , and have customers come visit me. Here is a link to one of my favorite blogs I ever wrote, about meeting Big Bill on Nantucket. He was a character who I spent a boozy night with long ago.

I was the itinerant t-shirt and hat guy. I worked with bars and restaurants and excavating companies who wanted sharp looking sweatshirts to give out to their customers. I remember a few memorable times out there, like the time I visited a cool bar in Madaket and Bill Belichick was there, and another time when I chatted up the late Tim Russert, who also liked The Westender, that bar with the greatest sunset view on Nantucket.

I’m glad that this visit won’t involve selling anybody anything. This time I’m there to write a story, to meet people, to have Mary paint landscapes, to ride bikes on their bike trails. The fun stuff I do now, instead of the mentally taxing work that once filled my days. It’s much better now, I must say.