Chianti Area

“Wine Down in Style!” - Reviewed by Deborah

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For many, Chianti is the quintessential heart of Tuscany, famous for its namesake wine which has been actively produced in the area since the 13th century when its undulating hills and valleys were first popularly classified as a wine region.

Geographically, Chianti refers to an area whose borders are somewhat hard to define as it speaks more of the terroir for wine-making and the official guidelines for the Chianti appellation than municipal or physical boundaries. For the sake of reference, one could say that Chianti’s contemporary borders encompass the provinces of Florence and Siena, extending eastward to include the Valdarno area and westward to embrace the Val d’Elsa region. Yet, it also stretches as far as Arezzo to the east, Pistoia to the north and Montepulciano to the south.

From Florence, take the SR222—also known as the New Chiantigiana Road—and you will soon enter the fabulous Chianti landscapes; while from Siena, you take the Old Chiantigiana Road. Though famously winding, roads in Chianti are fairly good, and you can get a glorious sense of the Tuscan countryside taking scenic drives or, better still, cycling. Get ready for rows upon rows of vines, cypress avenues, olive trees and splashes of yellow broom.

Make Wine, Not War
Historically, the area was a continuous battlefield from the Middle Ages to the Renaissance as Siena and Florence fought for dominance over these lands. Not surprisingly, you can still see the vestiges of the ancient power struggle as castles and towers still pepper the landscape. After the warring ended, many of these valleys were cleared for cultivation. Besides vineyards, you will also find chestnut and oak forests as well as olive groves.

Though winemaking had been popular in the region since the 13th century and can be traced to the Etruscan period almost two millennia earlier, it was the Grand Duke Cosme III Medici who made the Chianti borders official in 1716 by means of an edict. At that time, only the municipality of Gaiole, Castellina and Radda (which, today, still carry the title “in Chianti”) were part of the ancient Florentine Military League of Chianti whose symbol was, and still is, a black rooster.

Today, what is classified as Chianti extends over a much larger territory and the main towns in the region include Impruneta, San Casciano, Greve, Tavarnelle, Gaiole, Castellina, Castelnuovo and Radda, all of which are surrounded by smaller villages and hamlets. Many of these settlements are famed for their medieval convents, churches, fortresses, castles and towers, besides armies of vines standing to attention.


  • Tuscany, central Italy
  • 30 minutes to Florence International Airport
  • 3 hrs 30 mins to Rome International Airport
  • Ideal for visiting Siena, San Gimignano, Arezzo


  • Sightseeing – Day trips to Florence, Siena, San Gimignano and Arezzo.
  • Hiking and Cycling – This is a fabulous region for cycling and hiking.
  • Gastronomy – Discover the many local and regional dishes with plenty of restaurants to suit every taste and budget.
  • Wine Tastings – You will be spoiled for choice for wine tasting tours, with options for days tours and even wine classes.
  • Cooking Classes – Learn how to cook authentic Tuscan recipes from expert native chefs.