At Least You’re in Tuscany

By Sharon Sanders

Jennifer Criswell had guts.  She wasn’t rich. She wasn’t fluent in Italian. And, she was no longer of the age where people say things like, “Oh, she’s young. . . she’s just finding herself.”

Yet, she moved from New York City to live in Tuscany. As a local barrista quizzically asked when she told him she was living in Montepulciano: “Ma, per sempre?” (but, forever?)

Her companion was a beloved Weimaraner named Cinder who, as you might suppose, was also neither rich, fluent in Italian, nor a frisky pup. 

In At Least You’re in Tuscany: A Somewhat Disastrous Quest for the Sweet Life, Criswell shares the transformation with candor and humor. By her own admission, “It certainly wasn’t the sensible thing to do.”

Ten years before relocating, Criswell experienced an epiphany in Pienza, the last stay on her first trip to Italy, a three-week jaunt through the peninsula. Confiding in her journal, she realized that she no longer wanted to be a lawyer. She wanted to be a writer, and, more importantly, she wanted to be a writer in Italy.

Although her resolve was firm, the move was not fast. She writes, “My dream of Tuscany inspired me to start making changes. It took nine years, a move from Miami to New York—where I survived (just) as a dog walker on the Upper West Side—loads of Italian lessons, and three more trips before I hoisted sail on my Italian odyssey. But when you’re meant to be somewhere, everything in between feels like you’re treading water, just waiting for that wave to lift you and carry you onto the shore of your new land. My new land was Italy.”

A New Life in Italy

She chose Montepulciano (population of about 15,000), her favorite among the hill towns south of Siena, Tuscany, as her new home.

After moving into the apartment she had secured beforehand, finding work was first on her to-do list. She became intimately acquainted with the Comune (town hall) in her quest to wrap up her Italian citizenship. She had begun the process (three years earlier), as she was entitled to pursue citizenship because of her Sicilian ancestors on her mother’s side. She had obtained a permesso di soggiorno (stay permit) that allowed her to reside, but not work, in Italy. A key document was missing!

Desperate, she even sought restaurant work in nero (under the table) to no avail. False pride was not an option since she only had enough money to support herself for a few months. She quilted together an income from part-time stints teaching English, babysitting, and picking grapes during the vendemmia, an adventure she describes in hilarious and painful detail.

She chronicles challenges of adapting to small-town Tuscan culture—becoming a figure of local gossip—but also the triumph of forming new, real, friendships and navigating the daunting bureaucracy. I won’t give away the details because the tale is delicious, seasoned with an unshakeable fervor for Italy.

No matter how dark the circumstances, Criswell consoled herself with the mantra. . . “At least you’re in Tuscany.”

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