Tuscany is the famous region of Italy once inhabited by the Etruscans. It is Italian food & wine country, located south of Florence, extending westward out to the Mediterranean. The region’s wines are known worldwide, the most famous of which is Chianti. We recommend staying centrally in the region in Siena, a medieval walled city in the heart of Tuscany. When renting a car be aware of Siena’s parking situation – all four public parking lots are located a 10-minute walk outside the pedestrian city. Also, get a car with a GPS and change the language to English. After that you will be touring Tuscany easily.
North From Siena Toward Florence: Via Chiantigiana
Head north out of Siena toward Florence. Via Chiantigiana leads you through the Chianti Region. While the highway also leads to Florence, the smaller roads are more picturesque. Via Chiantigiana is known as one of the region’s best routes.
Radda di Chianti
The first stop along this route is Radda di Chianti, reachable in 45 minutes. The route takes you deep through the Tuscan countryside in the Chianti region, dotted with Cypress-lined Tuscan estates. This is a small, quaint city with the usual supply of gourmet stores and enoteca’s (wine bars). Have lunch al fresco at the Relais Vignale, drinking in the views of the Chianti hills.
Castellini di Chianti
Castellini di Chianti is another quaint town along this road, with more of an upscale feel and a hilltop castle tower. Recently Michelangelo was rumored to have lived here, although upon interview the townspeople claimed they’d never heard of this. Sit in one of the street cafes and have a glass of Chianti.
San Gimignano
San Gimignano is a spectacular medieval walled city. It’s many towers make it the skyscraper capital of medieval Europe. Walk up the hill to the city, shop in the gourmet and pottery shops and tour the museum.
South from Siena Toward Rome: Via Cassia
This ancient road heads toward Rome but you will be stopping at Montalcino – a spectacular Tuscan hill town known for its wine – Brunello di Montalcino.
Montalcino
This beautiful hilltop town offers expansive views from the parking area just past the city. From there, enter the city and head toward the Fortress di Montalcino – the castle at the top of the hill. You can wander around its ramparts and taste the Brunello di Montalcino wine in its small cafe, offering fresh food and excellent wine in an outdoor setting.
Pienza
Piena is known for being the filming location of Franco Zeffirelli’s Romeo and Juliet in the late 1960s. Though the story is set in Verona, Pienza’s main square is recognizable in the movie. It is another hilltop town with expansive views, gourmet shops and enoteca’s.
Siena
Siena is the centerpiece of Tuscan hill town life with a proud history of the Palio. The Palio is an intense, bareback horse race in the Piazza del Campo or the historic city center. The many neighborhoods of Siena all compete to win the Palio once a year, with the winner celebrating for several months afterward. The city boasts an amazing cathedral and a lively city center square encircled with cafes. One delicacy to try is the panforte – a bread/cake with fruit and nuts, similar to fruitcake.
