Rocca Aldobrandesca ruins, Sovana

View of Montalcino

Pienza in the springtime

A street cafe in Arezzo

Sunset in Siena

Val d'Orcia, central hilltop towns region

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Discover the Best of Chianti

Our book covers hundreds of locations within Tuscany. Here is a sample of some of our favorites places in Chianti:

Three of our favorite places to visit in Chianti

Volpaia


Volpaia is an enchanting twelfth-century hamlet that is one of the most pristine and picturesque villages in all of Tuscany. It has, in fact, been described as a fairy-tale town. The village has about 50 inhabitants, and a trip to Volpaia is truly a trip back in time. The village is comprised of various medieval buildings, each of which is used in some aspect of the production of the estate’s splendid wine, olive oil and vinegar. The most interesting structure is the deconsecrated Commenda di Sant’Eufrosino, designed by Michelozzo ca. 1443 to care for the many pilgrims passing through the area. Today the Commenda is used as Castello di Volpaia’s tasting room.

A trip to Volpaia is particularly sensational in May and June, when roses are in bloom. A visit in November or early December is another choice time because the olive presses are in full swing immediately after the olive harvest.

A visit to Volpaia is easy and enjoyable as long as you have the GPS coordinates. The drive up to Volpaia is beautiful, parking is easy and the town is so small you can’t miss the wine shop or either of the restaurants.

San Gimignano


San Gimignano is a small, well-preserved medieval town known primarily for the massive stone towers enclosed within its city walls. Fourteen towers remain out of 72 original towers built in San Gimignano during the eleventh through the thirteenth centuries. At that time, San Gimignano, never a peaceful place even during its heyday, was beset by feuding families representing both the Guelph and Ghibelline factions who built competing tower houses to demonstrate their relative wealth and power. When the height of the tower houses was limited by law, the most powerful families resorted to building twin towers to distinguish themselves from their rivals.

San Gimignano’s distinctive and startling skyline of fourteen towers encircled by medieval walls seems to soar above the bucolic and tranquil Tuscan countryside. San Gimignano has been described as “the Manhattan of Tuscany” and the reason is clear as you approach San Gimignano from afar. San Gimignano’s historic center has been named a UNESCO World Heritage Site, as its small, well-preserved historical center typifies the architecture of the Middle Ages, with its squares, streets, houses, palaces and fountains.

The village itself is very picturesque. There are two principal squares: the Piazza della Cisterna, with its lovely well and bordering tower houses, and the Piazza della Duomo, bordered by the Collegiata of Santa Maria Assunta and the Torre Grossa (Big Tower). Tea with Mussolini and Where Angels Fear to Tread, based on E.M. Forster’s novel of the same name, were both filmed here and gamers can explore fifteenth-century San Gimignano in the video game Assassin’s Creed II.

Monteriggioni

Monteriggioni, one of the most beautiful villages in Tuscany, is a small, completely intact walled village dating from medieval times. The village is a beautifully preserved example of medieval architecture that draws tourists, as well as medieval historians and archeologists. The village was built as a Ghibelline defensive outpost in the early thirteenth century.

Perched on a hill and featuring medieval walls and 14 towers, Monteriggioni is a stunning sight from the distance, particularly when lit at night, as it appears to float above the surrounding countryside.

Monteriggioni is known both to those who have studied Dante Alighieri’s The Divine Comedy and to computer game aficionados. Dante evoked Monteriggioni as he described hell as “like Monteriggioni whose round walls are crowned with towers like horrible giants circling the abyss.” Gamers know Monteriggioni as the basis for the dark and menacing medieval setting in Assassin’s Creed II and Assassin’s Creed: Brotherhood.

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Three of our favorite restaurants in Chianti

Da Delfina

Da Delfina is a Michelin-starred restaurant in Artimino, a small village on the western outskirts of Florence. Da Delfina has been in operation for many years and was originally a trattoria for hunters. Chef Carlo Cioni uses his mother Delfina’s recipes to create authentic and traditional Tuscan dishes. He uses local ingredients often sourced from the restaurant’s own garden or the surrounding countryside.

Eating at Da Delfina is truly a memorable experience. The restaurant is just outside the walls of Artimino and is situated on a hillside with a commanding view of the Arno River, olive groves, vineyards and the country villa of the famous Medici family. In summer, food is served on the terrace overlooking the countryside. In winter, the brick-clad interior rooms with an open kitchen and wood-burning stove create a cozy and rustic atmosphere.

Address: Via della Chiesa 1, Artimino 59015

Ristorante Enzo


Ristorante Enzo, a small, refined and excellent restaurant off the beaten path, specializes in contemporary versions of typical Sienese classics. Although the restaurant appears a bit formal with white tablecloths and gleaming glassware, the staff is very welcoming and immediately puts you at ease.

Enzo’s specialties include ribollita, homemade pasta and seafood offerings. The restaurant also has excellent homemade bread and a delightful amuse bouche. This is definitely a more upscale restaurant, with the obvious touch of an attentive, well-trained and creative chef.  This fine restaurant has a wide variety of offerings, including various prix fixe and à la carte options.

Address: Via di Camollia 49, Siena 53100

Ristoro di Lamole

Ristoro di Lamole is a moderately priced destination restaurant set in the classic Chianti countryside. The drive to Lamole is a scenic drive on winding roads leading halfway up the mountain to Lamole. Lamole is 9.5 km from Greve and the drive up the mountainside takes about 22 minutes. There is limited parking in Lamole but cars just park along the roadside in front of the restaurant.

Ristoro di Lamole offers some of the best alfresco dining in Chianti. The restaurant has a superb, western-facing terrace overlooking a valley resplendent with vineyards, olive groves and great views of the sunset. On a clear day, you may even see the towers of San Gimignano.

Address: Via di Lamole 6, Greve in Chianti 50022

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Three of our favorite places to stay in Chianti

Albergo l’Ultimo Mulino

Albergo l’Ultimo Mulino is a small and charming four-star hotel located in the countryside a few kilometers south of Radda in Chianti. Although l’Ultimo Mulino is a short drive off a paved road, it is completely surrounded by woods and is located near a river.

The hotel was a medieval mill that was converted into a hotel and it is an architectural marvel. The hotel has a dramatic entrance hall with 13 arches spanning the enclosure. It has many antique artifacts reminiscent of its past, including wooden mill axes, heavy chestnut beams and a stunning fireplace. A stone bridge spanning the bed of the old millstream serves as the stairs and hallway leading into the rooms.

The rooms are tastefully decorated in the style of typical Tuscan farmhouses. Beds are wrought iron and floors are terra-cotta. Exposed beams are used in the ceilings, and the structure retains some of its original stone walls.

Address: Località La Ripresa di Vistarenni, Gaiole in Chianti 53013

Casanova di Pescille Agriturismo

Casanova di Pescille Agriturismo is a family-run bed and breakfast located in a lovely country setting just two kilometers from San Gimignano. Although Pescille is close to San Gimignano, it is nestled in the middle of a nature reserve, making it seem quite remote from the hustle and bustle of San Gimignano. Pescille is a converted nineteenth-century stone farmhouse consisting of eight bed-and-breakfast rooms and one separate apartment for two. The rooms are decorated with antique furniture in a style consistent with their farmhouse origin. Each room has a private patio.

Pescille is highly recommended and can best be described as idyllic. Not only is the property itself beautiful, but the owners also provide a high level of service, including a restaurant with fabulous food, and cooking and saffron classes. The classes include lunch and are an excellent value for the money. The cooking class is 85 euros per person and includes lunch cooked by the students and wine. The course is limited to four participants, so you are bound to have a lot of hands-on experience. The saffron class is 45 euros per person and it, too, includes a lunch showcasing the many uses of saffron.

Address: Località Pescille, San Gimignano 53037

Villa Il Poggiale Dimorna Storica

Villa Il Poggiale is one of the oldest and most beautiful villas of San Casciano in Val di Pesa. The villa dates back to 1408 but has been fully restored to provide modern conveniences. The present interiors were designed in the 1800s in a Renaissance style with beautiful frescoes and painted doors.

Villa Il Poggiale’s chef prepares a simple but refined Tuscan buffet during high season (running from April 1 through October 31). The chef, who is on-site, explains the dishes prepared and shares some of his cooking secrets. The food at Villa Il Poggiale is excellent and a good value at 30 euros per person. If the dinner buffet is available, it is highly recommended for at least one of your nights at Villa Il Poggiale. The breakfast is a traditional Tuscan buffet with pastry, prosciutto, fruit, yogurt, fresh ricotta cheese, honey, jam, toast, cereal, juice, coffee and tea. The buffet includes a variety of excellent homemade cakes, tarts and brioche.

Address: Via Empolese 69, San Casciano Val di Pesa 50026

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One of our favorite wineries in Chianti

Castello di Verrazzano

Castello di Verrazzano is one of the best winery tours in Chianti. It is easy to drive to Verrazzano because it is located just off the Chiantigiana north of Greve in Chianti.
Verrazzano is a beautiful winery perched on a hillside overlooking a scenic valley planted with row upon row of grape vines. Verrazzano was originally an Etruscan settlement that was purchased by the Verrazzano family in the seventh century. The Castello itself is a commanding structure dating from the late Renaissance, with portions of the cellar dating from the 1100s.

Verrazzano offers a classic wine tour that takes an hour and a half and includes a tour of the gardens, wine cellars and other production areas. The tour guides speak excellent English, are very knowledgeable and make the tour a fun and memorable experience. The basic tour (called classic) includes wine tasting on the veranda overlooking the valley. The wine tasting is an informative session where you will learn how to properly taste and appreciate wine in the Italian tradition. The wine tasting includes generous portions of four classic wines, extra virgin olive oil, balsamic vinegar, Vin Santo and contucci (a kind of biscotti). The tour guide discusses the characteristics of each wine and the order in which they should be consumed.

Address: Località San Martino in Valle 12, Greve in Chianti 50022

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