CASTELNUOVO BERADENGA, ITALY — Guido jams my suitcases into the trunk of the sporty Italian car I've hired and hurries me into the driver’s seat. The peppy little porter at the Castel Monastero resort is anxious for me to start my drive through the surrounding Tuscan countryside before “the sun gets too high in the sky."
“The morning light is magical and you’ll see Tuscany in all its glory; so hurry,” says Guido as I bid him farewell in the dawn’s early light and head down the dusty road that connects the ritzy resort with the famed Chiantigiana (highway SR 222).
The Chiantigiana is one of the most travelled tourist routes in Italy because it links fabled Siena  — just 14km south of the resort — with fabulous Florence, 50km to the north. The road also cuts through Tuscany’s famed Chianti Classico wine region and introduces foreigners to the charming towns and villages that have survived and prospered off the grape for centuries.
Driving under the Tuscan sun is the most exhilarating of experiences. The Chiantigiana is lined with olive groves, lush vineyards, chestnut forests and sunflower-filled fields. What a picture!
Off in the distance, the famed Tuscan hills stand silhouetted against the early-morning brilliance — the sky’s palette of colours continuously changing as the sun slowly rises.

Above: Tuscany looks best in the early morning light.

A spider web of small roads leads off the Chiantigiana and takes drivers on a rollercoaster ride through sleepy villages that time has forgotten. At every bend in the road, I see stone bell towers sticking up like pins on a map and I’m tempted to leave the main highway to explore. However, I remember what Guido jokingly told me: “if you stop at every town along the road, it will take you three years to reach Florence.”
By the time I reach the outskirts of Villa a Sesta, however, curiosity gets the better of me. Lured by the small town’s terra cotta roofed homes and terraced vineyards that gently slope down to the highway, I give in to temptation and veer off the Chiantigiana.
I’m rewarded by lots of Instagram potential — old sand coloured buildings that lean, old people sharing early morning gossip and an old (9th-century) church that’s filled with 18th-century paintings and relics.
Located just 24km north of Siena, Villa a Sesta is home to just 77 people and one of Italy’s most famous restaurants, Bottega del Trenta (30), which is governed by legendary Chef Hélène Stoquelet.
The small, one-star Michelin property draws patrons from as far away as Florence on a daily basis and has become one of the favoured dining spots with international visitors who occupy rooms at the chic resorts scattered in this area of Tuscany.
My detour into Villa a Sesta was indeed rewarding, but now I’m well behind schedule. Guido would not be pleased. But on my way back to the Chiantigiana, I take a moment to stop at the highest point in the village and admire the rolling Tuscan landscape, which drifts off in all directions. The breathtaking scene is enhanced by the clumps of pencil straight cypress trees I see standing alone in the fields — like sentries guarding the UNESCO-protected panorama.

Above: The Chiantigiana is lined with olive groves and passes ancient villages where famous chefs call home.

The main highway is light of traffic so I quickly get back on schedule. Which is good, because I now have time to visit some other fabulous Tuscan towns, like:

Gaiole: Located at the crossroads of the Chianti and the Valdarno valley, this charming market town is filled with ochre-coloured buildings and is best known for its collection of historic castles and churches. The town’s oldest castle is the 13th-century Castello Cacchiano but the nearby Castello Brolio and Castello Monteluco are equally impressive and historic. The Castello Vertine, which sits just outside Gaiole is actually a Medieval walled city and a favourite with visiting tourists. Not to be outdone, Gaiole’s Church of Spaltenna, houses a 15th-century crucifix among its many treasures.

Radda: Stopping in this delightful town is like arriving in another time because behind its impressive Medieval wall, Raddas has changed little over the centuries. The former capital of Chianti has a number of important buildings to explore, like the Romanesque Church of San Niccolò, which dominates the main square.
There are a number of castles and fortified Medieval residences on the outskirts of Radda, as well, and the Museum of Sacred Art of Chianti.
Castellina: Located just 35km south of Florence, Castellina is one of the most important towns in the Chianti region because it was here, in 1924, that the Chianti Classico Consortium was formed to safeguard the purity of the region’s treasured wine. Nestled between the valleys of the  Arbia, Pesa and Elsa rivers, this charming city of 2,800 lucky residents is also very close to two of Italy’s most photographed towns, San Gimignano — a.k.a. the town of towers — and Monteriggioni, the walled town known for its Medieval fortifications and watchtowers.

Above: Pencil-straight cypress trees guard the Tuscany's UNESCO-protected landscape like soldiers.

Panzano: This is one of the most popular places in Chianti and in ancient times everyone fought to claim the town for their very own. In fact, Panzano was completely destroyed on two occasions — first in 1260 and again in 1397 — by the bitter rivals ruling Siena and Florence at the time. The only evidence of those Medieval clashes are now assembled in the town’s bell tower. The most striking building in Panzanno is the town’s castle, which stands behind a well-preserved wall. The Church of Santa Maria, the Parish Church of San Leolino and the Oratory of Saint Euphrosynus are all worth visiting. Lanzano is also well known for its annual wine festivals.

Greve: If you are travelling south from Florence to Siena, Greve is considered the gateway to the Chianti region. It’s also one of the most impressive towns in the area, thanks to the Castello Montefioralle, which sits perched above the main square, considered one of the most attractive in all of Italy. Greve is located at the crossroads of three important pilgrimage roads — the Chiantigiana, the road to Valdarno and the road to Val di Pesa. In the past, this important market town was ruled by Etruscans and Romans. Greve’s neo-Renaissance-style Town Hall and the elegant Church of Santa Croce, which is built over the ruins of a Medieval church, are all worth visiting.  This is also the birthplace of navigator Giovanni da Verrazzano, the man who discovered the bay of New York. The city’s famed Castello di Verrazzano features a great wine cellar and the local Wine Museum offers tastings of more than 100 types of Chianti wines. If you have time, a winding backroad leading from Greve takes you to the enchanting villages of Montefioralle and Badia a Passignano.
Unfortunately, my time is running short and Florence, the capital of Tuscany, beckons.
As I get closer to the city where Michelangelo, da Vinci and Botticelli created some of their greatest masterpieces, the landscape begins to change.
The rolling Tuscan terrain and enchanting terra cotta villages that have filled my wind screen much of the day are now replaced by drab, grey industrial structures.
So I take one last look in my rear-view mirror and toast all that I’ve seen along the Chianti highway.