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6 Must-Visit Tuscan Villages


Red terracotta roofs among waving fields of golden wheat, sit under rolling emerald hills. Vineyards of Sangiovese grapes stretch the earth in neat rows, while sunflowers and lavender contrast each other in explosions of color. Tuscany is much more than Florence, Pisa, and Siena. It is swaths of picturesque farmland, ancient churches in various states of disrepair, and secrets behind alleyways and unassuming cobblestone streets. In small villages, life, food, and culture is more authentic than in the tourist districts of the major cities. These are the must-visit Tuscan villages.

From far away, Monteriggioni looks like a medieval fortress—brick turrets around an imposing wall, centered between rolling hills and cypress trees. The village dates to the 13th century, built by the Sienese as a deterrent to the Florentines. The town’s most notable reference came when the poet Dante Alighieri used the circular architecture as a metaphor of the rings of the Inferno in his Divine Comedy. The village piazza contains a church dating to the 10th century, and the restaurant Il Pozzo, considered to be one of the best in Italy.

Greve In Chianti
Chianti wine is one of the iconic symbols of Tuscany. The classic wine and olive oil production centers on the tiny village of Greve, one of several towns in the Chianti region. Greve is one of the main producers of oil, wine, and truffles, and hosts the Chianti Classico Wine Festival every September. Original buildings dating to the 11th to 15th century surround the triangle shaped piazza. In the nearby commune of Montefioralle, a tiny home is the purported childhood home of explorer Amerigo Vespucci.

Pitigliano is a bastion of a town, built high upon a cliff-face in the province of Grosseto. Constructed on the outskirts of the Papal-States, the town, dating to the 13th century, became known for its Jewish community and synagogue, developing the name, Little Jerusalem. The town is unique in that it doesn’t have the charming characteristics of typical Tuscan towns, but its fortress-like demeanor gives it winding streets that lead to artistic and cultural treasures that developed outside of the influence of the Vatican States and the Grand Duchy of Tuscany.

This tiny hamlet in the province of Florence, is known as the birthplace of its most famous son, Leonardo da Vinci. Surrounded by vineyards and olive groves, the birthplace of Leonardo is in a farmhouse just over a mile outside of town. The one-room home is simple and modest, with a simple hearth and tablets on the walls recording his life. Also worth seeing is the 13th century church, and the Museo Leonardiano, the official da Vinci museum with working replicas of Leonardo’s inventions, based on his designs.

Set between the towns of Montalcino and Montepulciano, Pienza is a town that has changed little from its early Renaissance foundations. In fact, it is a prime example of historical architecture at its finest, as well as a prototype for the way Renaissance-era towns across Europe would be constructed, at the order of its most famous native, Pope Pius II. Less than 2,500 live here, living among the narrow streets of charming trattorie, cafés, and cheese shops. The town was built as the Pope’s utopian vacation home, and the Piccolomini Gardens in one of town’s palazzi, overlooks a breathtaking Tuscan landscape.

San Gimignano
San Gimignano is known as a medieval version of Manhattan. 72-towers, each built by a prominent family as a show of power, dot the skyline of this picturesque town. Historically, San Gimignano was a crucial trade city between Florence and Rome, and an important rest point for Catholic pilgrims. They were influential in producing Vernaccia wine, a favorite of intellectuals and important figures of the Catholic Church. Art is prevalent here, such as in the Sant’Agostino Church featuring a multitude of work by Renaissance artists, and fine examples of Roman and Gothic architecture.


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