The word Chianti evokes images of tasty light red wines served from strange squat bottles wrapped in straw, marked with the telltale black rooster emblem on its neck. Though most actually come in conventional bottles, these wines are produced among stunning rolling hills in an area between the two pillar cities of Tuscany - Florence and Siena. One of the truly great Italian experiences is spending a few days driving or walking through the Chianti countryside with its quilt of hillside vineyards, olive groves and small forests on a backdrop of ancient churches, medieval walled towns, elegant villas, stone farmhouses and historic Florentine castles - almost unchanged from the superb Renaissance images of centuries ago.
Tuscany is a great place to open the wallet. Blessed with some of the finest hotels in Italy, the region offers opportunities to enjoy beautiful accommodation and sumptuous dining in picturesque surroundings on the grounds of working vineyards and olive farms.
Each of the four main Chianti towns (Greve, Castellina, Radda and Gaoile) have their own charm but the central Radda has best preserved its original character. While a car makes visiting the various small towns and villages much easier than the limited public transport, one highlight is a loop walk of around twelve kilometers between Radda and Gaoile (get a map to assist) through a number of enchanting Chianti villages and wineries.
From Radda, walk past a number of villages dotted on the rolling hills to the idyllic fortified hillside hamlet of Vertine. Walking under the entry arch (top photo) as inhabitants have done for almost ten centuries and past the stone keep and bell tower, the walled village of around thirty houses lining a circular street seems unchanged from the middle ages. There is an austere harmony about Vertine with its roughened wall exteriors built of stones that alternate from white to deep orange-brown. A small bar near the arch offers tasty Tuscan treats washed down with a glass (or two) of wine produced from the vineyards which radiate down the gentle slopes from this charming medieval village.
A little further on is the historic village of Spaltenna with its fortified pieve (rural church) and monastery, built in 1030, and now a hotel and restaurant. Nearby Gaoile is Chianti’s market town with a piazza of restaurants, cafes and wine shops and a good place for lunch.
Returning to Radda, the honey-coloured village of Volpaia is a highlight. Within its ancient walls, the castle was converted into a premium winery and olive press around forty years ago. This village slowly unveils itself as you wander the narrow curved cobblestone laneways, past an unusual eight-sided well and a church, now converted to a cellar. The wine tasting is quite a show including a memorable red with the lyrical name of Balifico.
Wander back to Radda and reflect on a wonderful outdoors day strolling in the Chianti countryside, uncovering historic hamlets while feasting on the centuries old delights of Tuscan food and wine. The travel wonders of Chianti epitomise the Tuscany region and there is no better way to fully sense and experience it than to spend a relaxed day strolling the gentle slopes of this historic region.
The word Chianti evokes images of tasty light red wines served from strange squat bottles wrapped in straw, marked with the telltale black rooster emblem on its neck. Though most actually come in conventional bottles, these wines are produced among stunning rolling hills in an area between the two pillar cities of Tuscany - Florence and Siena. One of the truly great Italian experiences is spending a few days driving or walking through the Chianti countryside with its quilt of hillside vineyards, olive groves and small forests on a backdrop of ancient churches, medieval walled towns, elegant villas, stone farmhouses and historic Florentine castles - almost unchanged from the superb Renaissance images of centuries ago.
Tuscany is a great place to open the wallet. Blessed with some of the finest hotels in Italy, the region offers opportunities to enjoy beautiful accommodation and sumptuous dining in picturesque surroundings on the grounds of working vineyards and olive farms. 
Each of the four main Chianti towns (Greve, Castellina, Radda and Gaoile) have their own charm but the central Radda has best preserved its original character. While a car makes visiting the various small towns and villages much easier than the limited public transport, one highlight is a loop walk of around twelve kilometers between Radda and Gaoile (get a map to assist) through a number of enchanting Chianti villages and wineries. 
From Radda, walk past a number of villages dotted on the rolling hills to the idyllic fortified hillside hamlet of Vertine. Walking under the entry arch (top photo) as inhabitants have done for almost ten centuries and past the stone keep and bell tower, the walled village of around thirty houses lining a circular street seems unchanged from the middle ages. There is an austere harmony about Vertine with its roughened wall exteriors built of stones that alternate from white to deep orange-brown. A small bar near the arch offers tasty Tuscan treats washed down with a glass (or two) of wine produced from the vineyards which radiate down the gentle slopes from this charming medieval village.
A little further on is the historic village of Spaltenna with its fortified pieve (rural church) and monastery, built in 1030, and now a hotel and restaurant. Nearby Gaoile is Chianti’s market town with a piazza of restaurants, cafes and wine shops and a good place for lunch. 
Returning to Radda, the honey-coloured village of Volpaia is a highlight. Within its ancient walls, the castle was converted into a premium winery and olive press around forty years ago. This village slowly unveils itself as you wander the narrow curved cobblestone laneways, past an unusual eight-sided well and a church, now converted to a cellar. The wine tasting is quite a show including a memorable red with the lyrical name of Balifico.
Wander back to Radda and reflect on a wonderful outdoors day strolling in the Chianti countryside, uncovering historic hamlets while feasting on the centuries old delights of Tuscan food and wine. The travel wonders of Chianti epitomise the Tuscany region and there is no better way to fully sense and experience it than to spend a relaxed day strolling the gentle slopes of this historic region.
