"Head for the Hilltop Make the steep ascent to this walled hilltop town and you’ll find yourself transported back in time—to the Renaissance, medieval, Roman, and even ancient Etruscan periods. Thought to be founded as far back as the 7th century B.C.E., Volterra is a favorite among the Tuscan hill towns for its spectacular setting and its wealth of notable sites. The latter range from the 1st-century B.C.E. Roman Theater and Etruscan-era city walls, gates, and tombs to the 13th-century Palazzo dei Priori town hall and cathedral (home to an array of sculptures and paintings). The Guarnacci Etruscan Museum showcases thousands of funeral urns from as far back as the Hellenic period, while the former Medici fortress—built in the late 1400s—now houses both a high-security prison and, several times a year, a gourmet pop-up restaurant staffed by inmates (reservations are hard to come by and, naturally, involve detailed security measures). Soak up the town’s rhythm at the main Piazza dei Priori, then browse the boutiques and workshops packed with artworks from massive sculptures to travel-friendly trinkets made with famous Volterra alabaster, another tradition dating back to Etruscan times."

"Charming Tuscan Hill Town Montepulciano is a charming hill town in Tuscany. Walk the streets to get a feel for its appeal. On the outskirts of town visit San Biagio, a 16th-century church. This late-Renaissance building was constructed on the site of a pre-existing Palaeochristian pieve (a type of church) dedicated to Saint Mary and subsequently to Saint Blaise. By the early 16th century the pieve had fallen into ruin, its remains including a wall with a fresco of the Madonna with child, and Saint Francis, from a 14th-century Sienese painter. The church today has a circular plan with a large dome over a terrace and a squared tambour. The exterior, with two bell towers, is built in white travertine. It's a lovely church worth the hike from the town center."

"Walking through Ruins in Tuscany Forty-five minutes to an hour away from Florence awaits the medieval hilltop town of San Gimignano, a UNESCO World Heritage Site. Bordered by 13th-century walls and featuring a triangular central square lined with historic houses, the town is best-known for its "skyline" of medieval towers and its 12th-century church with frescoes by Ghirlandaio. The town is popular with tourists, who arrive in packs by bus, so it can be difficult to navigate the old town in the afternoon. While they are scouring the sites, I suggest following the city walls to the opposite side of the entrance, where the walls are slightly crumbled. Here you will see sweeping views of the famous Tuscan countryside, with its hills dotted with vineyards, old villas, and olive trees. Few visitors venture outside the city walls, but I recommend it. Be adventurous and you'll find signs of the city that once was. The ruins have been overrun by nature, with olive trees running along walls that once saw the plague, and hidden steps leading you to views of the city against a backdrop of green."

"The Ideal City To celebrate his becoming Pope, the 15th-century Pius II commissioned Florentine architect Bernardo Gambarelli to reimagine his birthplace—then named Corsignano—as the ideal Renaissance town, using then-revolutionary humanist urban planning concepts. The result was Pienza (renamed in the Pope’s honor), a town so perfectly ordered and livable, its layout was quickly imitated all over Italy and then eventually throughout Europe. Wander around Pienza today and it still seems pretty idyllic (it's designated a UNESCO World Heritage Site), with the streets in the historic center boasting adorable names (think “Love Street” and “Kiss Street”) and the views postcard-perfect down every lane and out to the Val d’Orcia countryside. And then there’s the smell of cheese: Pienza is famous for sheep’s milk–based pecorino, and its scent wafts out of every other doorway; it’s strong at first, but once you’ve tasted the cheese, and seen how it’s made, you’ll come to love it. Make sure to check out the trapezoidal main piazza, which is bordered by the Duomo and three historic palazzi. Palazzo Vescovile is home to two museums focusing on textiles and religious artifacts, and the Palazzo Piccolomini boasts a stunning internal courtyard and Italian Renaissance garden."

"Summer in Tuscany Last summer we spent an unforgettable week in Tuscany, in the little town of Castiglione della Pescaia. It's a typical small coastal town, with people on scooters everywhere, terraces full of people enjoying cappuccinos, and fishermen going out to sea early in the morning and being awaited in the evening by customers looking for the freshest catch. Castiglione della Pescaia is known for its beaches, and a visit to the church on the hill in the center of town will give you some spectacular views at sunset. It is also very close to a few beautiful vineyards. Holiday rentals are not as expensive as in other parts of Tuscany, and the location is perfect if you want to visit Rome , Pisa, Florence , or Cinque Terre, as the town is within two or three hours' drive from all of them."

"Summer (and Carnival) Fun For sand, sun, and fun on the Tuscan Riviera, head to this idyllic town bordered by the Tyrrhenian Sea on one side and the peaks of Masa Carrara (home to the famous while marble of the same name) on the other. Originally built as the port for nearby Lucca, the town now draws summer crowds with six miles of sandy shores; there are both private and public beaches, with most of the latter set in the protected Migliarino San Rossore Massaciuccoli regional park. Mingle with bronzed beachgoers, locals, and jet-setters along the nearly-two-mile-long La Passeggiata, a pedestrian street running parallel to the water and lined with shops, restaurants, and cafes; the composer Puccini regularly found inspiration along this stretch. But summer is not the only high season here: The annual Carnevale, taking place over the four weeks leading up to Lent, is considered one of the top carnival experiences in the world, and draws thousands of revelers with its elaborate floats, over-the-top costumes, and lively street parties."

"Hidden Gems One of the most important cities during the Etruscan period, then later made rich by its goldsmith traditions, this city, just a short drive southeast from Florence, is something of an insider’s favorite when visiting Tuscany. With fewer crowds, you’ll have more room to breathe while exploring sites like the Church of San Francesco (with its stunning early-Renaissance frescos by Piero dell Francesca), the ruins of the Roman amphitheater, the Medicean Fortress, and the Church of San Domenico, home to a wooden crucifix by Cimabue. Arezzo is also a favorite among treasure seekers, as it’s home to a number of well-stocked antique shops and one of the best antiques fairs in Tuscany. Running since 1968, the latter takes place the weekend of the first Sunday of each month, and features over 500 vendors and up to 30,000 shoppers looking to score a find. Taking place July to September, the Terre d’Arezzo Music Festival also draws big crowds to the piazza with its calendar of classical concerts and opera performances."

"Wine, Olive Oil, and Beautiful Views in Monteriggioni Monteriggioni is a tiny walled town populated by a handful of shops and restaurants. But, in its day, it was front line defence for Siena from the rival Florentines. In fact, it was so important that the town was even mentioned in Dante’s Divine Comedy . The views from the castle walls are splendid—rolling hills and wineries, as far as the eye can see. From here, it’s easy to see why Monteriggioni was a strategic lookout point. But the best thing about Monteriggioni is the local wine, Monte Chiaro, which you can taste at the nearby winery. Monte Chiaro offers a range of wines, from bright whites to the richest of reds. They are all superb but the 345 Chianti, the Brunello di Montalcino, and the Primum Vinum all found their way home with us. The shop also stocks local olive oil, honey, and other tasty regional treats."

"Home of the Red While wine production has been a part of Montalcino life for centuries, it took the 1888 creation of Brunello di Montalcino—a gorgeous twist on Chianti blends made with 100 percent Sangiovese grapes—to put the medieval town’s name on everyone’s lips. Wine fans will delight in visiting area vineyards and producers, many still small and family-owned, and sampling vintages both at the source and in local bars. If you’re not a drinker, never fear: There’s plenty else in the fairy-tale town that will charm you, including the Piazza del Popolo main square, with its Gothic loggia; the 14th-century Rocca fortress, boasting breathtakingly vast views from its ramparts (a hotspot during sunset); and the Museo del Vetro, a glass museum set inside a former castle that showcases delicate works by the ancient Egyptians on down to modern-day Venetians. Stroll the maze-like cobblestone streets, popping into the small shops and cafés, to get a feel for the place. Better yet, visit during a festival; among the annual celebrations are Montalcino Honey Week in September and the Jazz & Wine Festival each July."