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Under the Tuscan Sun: A Spring Itinerary for the Ancient Walled City of San Gimignano

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San Gimignano: The guide books say that it is one of the most popular tourist towns in Tuscany. But when two friends and I headed to the tiny, ancient, walled city of towers this week, we found that San Gimignano's charm is in experiencing the unexpected, finding the tiny streets and shops off the main square and living like a local.

Our first smart choice: Booking a villa through Parker Villas, a company in Boston owned by Italians who works with locals to find wonderful properties for rent and then puts you together with a local "concierge" to help you figure out the best, off-the-beaten track activities and restaurants. Parker Villas is a very special company in that they really know the areas and put together great itineraries (if you want them) or suggestions, complete with directions, phone numbers, and the local "concierge" in each region available at any time if you need her. For first time travelers to Italy, their system is a godsend, outlining every step of a successful and memorable trip; for me and my friends, more frequent Italian visitors, the suggestions they offered helped us get an insider's experience instead of revisiting the more touristy sites.

Our San Gimignano "home" was a perfect example. Although Mario, the owner of Parker Villas, had told me that Zafferano was spectacular, I really don't think he did it credit. The villa -- really an apartment -- is beyond special; it is hidden in one of the famous towers, overlooking the main piazza on one side and the countryside on the other, with a roof deck that offers almost 360 degree panoramic views.

Probably our next best decision was our plan to stay away from the typical tourist spots, to embrace the quiet, relaxed pace of Tuscany. No running to take photos or purchase souvenirs for us; instead, we spent our first afternoon after a long flight to Florence just walking around the stone streets, trying to shake off the jet lag (walking is the only choice, as we found out after almost getting arrested -- e vietator guidare nel centro (you are not allowed to drive in the center of San Gimignano!)). And to see the countryside? We inhaled pasta carbonara and pappardelle with wild boar sauce at Le Vecchie Mura, a family-owned restaurant with a panoramic outdoor terrace only a five-minute walk from our villa.

Our "concierge," Serena, set us up on day two with a tour of some of the lesser-known hill towns (Semifonte and Petrognano) by a local who was actually a doctor but an art and architecture aficionado. The best part: We didn't see an American anywhere! The towns were about half an hour away from San Gimignano, easily to access by rental car but virtually unknown to tourists. After a morning of exploring, we headed to Oleandolo, the organic farm where the doctor and his wife grow olives and heirloom fruits. Anna, the wife, once had a cooking show on Italian television, but now she cooks lunch for guests; for EU40-70 she will seat you with her husband and mother at her own dining room table and serve you a four course meal, made exclusively from things (except for meat) she grows on her land. By special request, Anna offers cooking classes, even allowing foreign visitors to stay in a guestroom in her old farmhouse for several days to learn a week's worth of dishes.

By Day 3, we had enough energy to hit the Tuscan countryside. I've always had a thing for Vespas, and the chance to explore the hill towns on a tiny scooter was more than I could resist. With Tuscany Vespa Tours, my friends and I rode for about three hours through the Chianti countryside (stopping to take photos from isolated hilltops), plus ate a three-course lunch and toured a twelfth- century castle that is still home to a count and countess, members of the original family. The tours are guided by native English speakers, and they offer bicycle tours, too (maybe next trip!).

On day four, a Tuesday, the town was quiet; perhaps tourist buses don't head to San Gimignano midweek? This was our chance to have the fourteenth-century cathedral (famous for its frescoes) to ourselves, plus do some shopping. Our suggestions after a full day? The thin-crust prosciutto pizza at Pizzeria Ibiga on Via San Giovanni, the blueberry/ricotta gelato at Gelateria dell'Olma in the main square, leather goods at Fantasie Sotto Le Torri, a tiny shop where the owner makes bags by hand and sells them for about half the cost of the same type of goods found in Florence, and a quiet dinner of carbonara with artichokes and truffles by the panoramic window at Ristorante BelSoggiorno on Via San Giovanni.

Even though there's so much more to do in San Gimignano, our time was limited. On our last day, we spent the spent the morning on our roof terrace, looking out at the countryside, eating breakfast and drinking coffee. And then? We packed and left for the next Italian villa (more to come on that!).

In short, San Gimignano is about as charming a town as you'll find anywhere in the world. The key to a trip you'll never forget? Getting off the beaten path, avoiding the throngs of tourists, and exploring the tiny streets.

Photo credit: Ward Nipper

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