Southwest Florida dreamin’

A version of this story appears in the Feb. 29, 2012, edition of the Rutland County Express.

Call it a tale of two Naples (Napleses? Napoli?). In Rutland, the connection to towns of this name runs deep — a generationally-embedded locus where, for some, the two have become touchstones of family and heritage.

There is the Naples in southwest Italy, from where, at the turn of the last century, many Rutland families (mine included) emigrated. And there is the Naples of southwest Florida, to where many of them make their second (and final) flight. It’s the Alpha and the Omega: from whence we came, hence shall we proceed.

Over the years, Naples, Fla., has become a popular winter destination for Rutlanders of a certain age. My father — a man who since his youth has always wanted to be of a certain age — has made Naples my family’s go-to vacation spot for as long as I can remember.

Tiring of the Vermont winter, my father long ago resolved to spend as much of it as possible in Naples. In my youth, this included making arrangements to take me out of school for weeks at a time. Until fifth grade, I spent January through March in Florida with my parents, being tutored by my mother. Aside from the complete lack of socialization with people my own age (imagine Finch from “American Pie,” but 8 and chubby), it wasn’t a bad life: schoolwork until noon, then tennis lessons or a trip to the beach.

My siblings, who were all in their 20s at the time, only made fleeting appearances, visiting for a week or so before heading back up north. As I grew older (and heard the stories), I learned that this arrangement was much more preferable.

However, all this time in Florida, meant that the Vermont winters of my childhood were confined to December and early January. As a result, I am an oddity around these parts: a Vermonter that can’t ski. It’s an explanation I am forced to run through at least once every winter, as incredulous flatlanders and natives alike marvel that such a thing can even exist.

You’d think, then, that after all this time spent in Florida, I’d at least have learned an equivalent sport, like surfing or sailing. Alas, after a childhood spent wintering with blue hairs, the only skill I picked up was how to order off the early bird special menu after 6 p.m.

In the almost 30 years that I’ve been visiting, I’ve seen the area change dramatically. I’ll be blunt: To me, Florida is an overdeveloped, poorly planned, inauthentic strip mall that brings issues of consumerism, class and race into stark focus. As a colleague and Florida-native put it to me not too long ago, “It’s hard to put down roots when all there is is sand.”

My first memories of Naples are of a sleepy albeit moderately wealthy retirement community. The highlight of Fifth Avenue (the heart of its downtown area) was an old-time ice cream shop. That peacefulness is what compelled my parents choose Naples over the crowded and rushed east coast where many of our cousins settled.

Today, that is no longer the case. When I last visited Naples in 2009, streets I had known and walked scores of times were barely recognizable. Fifth Avenue bustled with trendy restaurants, pricey boutiques and showy luxury cars. Even the old scoop shop has received a gaudy “Real Housewives”-style makeover.

Nonetheless, there is still something familiar about being there. Despite the sprawl and wastefulness and faux culture, it still feels comfortable, like an extension of Rutland — a southern analog.
This time of year, I can hear Naples beckon. Especially this winter, which has been more purgatory than season — too warm for snow, too cold for spring; it’s a gray, empty state of being that has us begging for deliverance, or at least a long weekend to someplace warm and familiar.

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