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Centrally located in Italy’s famed Chianti wine region, just a short drive from Siena, lies Castellina with its lovely terra-cotta and stone structures surrounded by vineyards on gently rolling hills. It’s not just a place for Chianti Classico, but also the best gelato in Tuscany, with a slice of history from the Bronze Age. Visitors can enjoy a leisurely stroll through the pedestrian-only thoroughfare, dine at restaurants under vaulted ceilings, and explore underground wine cellars and historical ruins. Here’s a look at how to experience all that Castellina has to offer for €75.  

Stroll Via Ferruccio and Via della Volte 

Amble through the vehicle-free main street Via Ferruccio, peppered with restaurants, cafes, and shops. Every Saturday from 8 a.m. to 1 p.m, the weekly market here presents vendors selling clothes, shoes, fruit and vegetables, and household items. Explore the underground tunnel, Via della Volte, that runs under the eastern border wall that was once used by guards during wartime. It now features unique merchants and eateries, providing a much needed respite from the Tuscan sun.

Visit the Church of San Salvatore 

At the town center sits the Church of San Salvatore, a 16th-century edifice rebuilt in neo-Romanesque style in 1945 following World War II. It displays a fresco by Lorenzo Bicci depicting the Virgin Mary with Child, and a wooden statue of St. Barnabas, the former patron saint of the town during the Renaissance. At night, strings of lights from the church brighten the square, illuminating the paths with their soft glow, a scene right out of a romantic movie.

Explore the Rocca (Fortress) and Archaeological Museum of Chianti (€5 per person/$5.90 USD)

The main fortification, called the Rocca, features a giant 14th-century tower built for defense in the Middle Ages and offers a magnificent view of the town and nearby countryside. Within, visit the Archaeological Museum of Chianti, which exhibits ancient artifacts from excavations, including many from Etruscan settlements discovered over a century ago. If you can’t get enough, visit the nearby burial mound at Monte Calvario. From the remains found nearby, it’s been determined that humans inhabited the area as early as the 7th century B.C. It doesn’t get any better for those wanting to trace the footsteps of our ancestors.

Eat Lunch at Antica Trattoria la Torre (€20 per person/$23.60 USD)

Just steps from the fortress sits Antica Trattoria la Torre, a charming ristorante with al fresco dining. Outdoor seating fills up fast with locals and tourists, but the wait is worth it when you can feast on Zuppa di Magro (vegetable Tuscan soup), Pici (handmade strand pasta) or Gnocchi Di Patate (potato gnocchi) and tiramisu. The service charge is included in the check.

Taste Wine at Antica Fattoria La Castellina (from €5/$5.90)

The region’s best-known winery, La Castellina, offers tastings with the convenience of self-serve wine dispensers. Get up to 10 tastings for €10. Located at nearly the edge of the main street, this shop is a perfect way to experience the wine of Chianti without driving. Take the stairs two levels down to an intimate cellar housing bottles dating back more than 30 years. Cozy couches and large tables adorn the subterranean level with additional dispensers.

Have Dinner at Sotto Le Volte (€40 per person with wine/$47.20 USD)

Under the arches of Castellina’s walkway hides the town’s best kept secret, Sotto Le Volte (Under the Lights), with “outdoor” seating under the vaulted ceiling of the tunnel. With a warm atmosphere, cream tablecloths, and soothing candles, this locale makes for such a romantic setting you'd never believe it was once a bomb shelter during the war. The menu is eminently Tuscan, with offerings such as hearty soups, handmade pappardelle, and fresh seafood. The wine list is extensive, with over 150 labels. Try a glass of the Chianti Classico Riserva with your entree.

Indulge in Dessert at Antica Delizia (starting from €3.50/$4.10 USD)

Castellina has one of the best gelato shops in Tuscany: Antica Delizia, located at the entrance to Castellina from Florence. Choose from unique flavors and combinations of fruits and herbs you can’t find elsewhere, including raspberry with rosemary, lemon mint, and strawberry sage. At this family run gelateria, all batches are made fresh daily with natural ingredients and fruits in season, and served with amore.

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