Florence and Siena, both World Heritage-listed cities, boast a wealth of Renaissance magnificent art and architecture, and are also noted for their excellent cuisines. Montepulciano is a beautiful hilltop town known for some of Tuscany’s best wines. Just a few of the itinerary attractions on this drive through beautiful Tuscany.

Total drive approx: 358 kms

Day One. Depart: Florence   O/night Siena   Approx 78 kms

Florence -- a city of many treasures

Your first day’s drive leads between two of Europe’s most beautiful Renaissance treasures, Florence and Siena. The route takes you over rolling, scenic hills, past well-tended vineyards and proud Tuscan family farmhouses, with time to stop and enjoy ancient villages and historic castles -- and taste an excellent wine or two. You will be travelling through centre of the Chianti wine region. Known as the Chiantigiana, it's one of Italy’s most pleasant driving routes.

Don’t forget: if you are going to taste those wonderful ruby red Chiantis along the way, travel with a dedicated driver. You know it makes sense.

Leaving Florence head south to join the Strada Regionale 222 (SR222). At the village of San Piero a Ema, the road passes under the A1 autostrada and leads on to Grassina. Because it is close to two rivers once used by local women to do the laundry of wealthy families living in nearby Florence, this small town was known for years as ‘the land of the laundresses’.

A couple of kilometres south of Grassina you pass the Ugolino golf course to your left. The club, which welcomes visiting golfers, has an interesting history.  It began when the Florence Golf Club was founded at the end of the 19th century by members of the city’s English colony ( it was obviously not just a group of eccentric poets, writers and artists): it was the first golfing club in Italy.

The Florence course was moved after World War One, and later someone came up with the idea of moving it again. The Ugolino course was created in the early 1930s and since then has hosted many international opens. If you want to play the course, remember that reservations cannot be made at weekends, public holidays or during competitions – and all players are required to have a handicap certificate not over 36.

From Grassina the SR222 takes you on through several small winemaking villages -- take a detour off the Chiantigiana now and then to explore them. They are linked by a tangled network of secondary roads. Don’t worry about getting lost as they all lead back to the main road.

History and art buffs will want to stop in Vicchiomaggio. Leonardo da Vinci once spent some time at its medieval castle. If your budget stretches to it, Castello Vicchiomaggio, which is also a working wine estate, offers excellent accommodation, a restaurant to match and cooking classes. From mid-March until the end of December, there are wine tours available at the castle. They are run daily except Saturdays between 10.00 and 18.30.

The route leads on to the pleasant market town of Greve in Chianti (several villages have tagged the ‘in Chianti’ label to their name). A couple of kilometres before you get to Greve, turn off to your right and make the short uphill drive to tiny Montefioralle, a strikingly pretty village steeped in history.

Montefioralle was a stronghold during the wars between Florence and Siena, part of Tuscany’s volatile past. Apart from intermittent wars between the two cities, the region has at times been ruled by the Spanish, the Austrian Habsburgs and Napoleon from France. The origins of Montefioralle castle goes back almost a thousand years: it is actually a fortified monastery built by a German monk long before the conflicts that followed. Several wealthy Tuscan families have owned the castle over the years.

Its strategic importance to warring dukes and princes has long gone, and Montefioralle is now a somewhat slumberous village that wakes up only in September for its popular annual wine festival.  American visitors passing this way will be interested to know that Montefioralle is the ancestral home of Amerigo Vespucci, the 16th century map maker and navigator after whom America was named.

From Montefioralle, head back down the hill and continue a couple of kilometres to Greve in Chianti, the unofficial capital of the region. Before Greve became part of the newly united Italy in 1861 it was a proud independent town. Greve’s big claim to fame these days is doubtless its annual wine fair. Held on the second weekend of September, it’s the biggest in Tuscany. The whole region has celebrations around this time and accommodation should be arranged well in advance.

Greve -- a Tuscan wine capital

A bit of Tuscan trivia: if you have ever crossed from Brooklyn to Staten Island on the Verrazzano Bridge in New York and wondered where it got its name, you will find the answer in Greve. There is a statue in the main square in honour of Giovanni da Verrazzano, the discoverer of what is now New York harbour. The locals will proudly tell you that da Verrazzano was a local boy who made good, but some historians have raised doubts, saying he was actually born in France. You drink your Chianti, you take your choice.

Le Cantine di Greve in Chianti offers close to 150 wines to taste, as well as other local specialities, such as the salty pecorino sheep’s cheese, finocchiona (a Tuscan salami made with pork meat and fennel), grappa and some of the best olive oil to be found anywhere in Tuscany. For wine lovers and foodies, it’s a good reason to spend a whole day (or longer) in Greve.

Travelling south you pass through Pananzo, a village well known for the intricate embroidery made by local women. Originally a medieval castle, Pananzo has preserved some of its old walls and towers.

Castellina -- an ancient outpost

Next comes Castellina, boldly perched on a ridge and offering superb views. This village was an important outpost during the conflicts between Florence and Siena – today’s town hall is located in what was once a medieval fortress. As with all the old villages and town along the Chiantigiana, you need to explore Castelinna by foot. Take a walk along the Via delle Volte, the old arched laneway that runs along the east side of the city walls – and visit the Etruscan tomb just outside of the village.

From Castellina, continue south on the SR222 all the way to Siena.

A reminder: just as many of the villages you have stopped at along the way have been vehicle free, the centre of Siena is also accessible only by foot. Cars are prohibited. If you are staying in a hotel in the centre of Siena, you are allowed to drive there to unload your luggage – but you will need a evidence of your hotel confirmation. There are several good hotels, guest-houses and farm-stays close to the city.

You might want to stay longer in Siena and make it a base for exploring the many picturesque little villages in the region. You will eat well, and enjoy some wonderful wines. In short, it’s a foodies’ paradise.

Accommodation options: Borgo Grondaie, a converted Tuscan farmhouse two kilometres outside of the city centre; Castel Monastero, about twenty kilometres east of the city; Hotel Athena is located in the city.

Day 2. Depart Siena   O/night: Montepulciano  Approx 105 kms

Like Florence, Siena is famous for its art museums and medieval achitecture – which means there is plenty to see before continuing on your journey to Montepulciano, a town known for some of the best wines in Tuscany.

The colours that symbolise Siena - black and white – can be seen in the imposing Sienna Cathedral, or duomo, which has the finest marble pulpit and mosaic marble floors to be seen in any Italian church or cathedral. In years gone by vast sums of money were donated by the wealthy merchants of Siena to make their city as beautiful as Florence. And it shows at every turn.

While in the cathedral make sure you visit the Piccolomini Library. The Piccolomini family were extremely powerful back in the 1400s: Enea Silvio Piccolomini was elected as Pope Pius II. The library was built by Pope Pius II's nephew (who later became Pope Pius III)  in memory of his uncle and to conserve the rich collection of manuscripts he had lovingly collected.

The main square of Siena is the sloping Piazza del Campo, with unique red brick paving shaped like a large clamshell. The focal point of the square is the Palazzo Pubblico, or town hall, with its unusual frescoes -- collectively known as the Allegory and Effects of Good and Bad Government.

Art lovers will also want to wander around the Pinacoteca Nazionale, or ‘national art gallery’, located in the Palazzo Buonsignor. It contains a remarkable collection of much-admired 13-16th Sienese paintings.

The horse race in Siena

The biggest local event is the Palio di Siena, a horse race that takes place twice a year on the tight cornered main square (early July and mid-August ). Jockeys ride bareback in this frantic race. It’s all over in a couple of minutes, and as the winner crosses the line to the cheers of the festive crowd the partying kicks off.  It may not be the Derby, the Melbourne Cup or anything else in that league, but the atmosphere at the Palio di Siena horse race buzzes with similar excitement.

It takes little less than three hours to drive to from Siena to Montepulciano. Drive south on the SR2 in the direction of Buonconvento, which sits on the edge of the Val d’Orcia surrounded by medieval walls. Like so many villages along this route, Buonconvento oozes with tales of centuries-old political intrigue.

About half-and-hour’s drive further you reach San Quirico d'Orcia. It’s only a small village, but nevertheless boasts a castle and four churches. Take a little time to explore and then continue north-east on the Strada Provinciale (SP 146), which will take you through the rippling Tuscan hills of the Val d’Orcia to Pienza. The spectacular Val d’Orcia is also World Heritage-listed, and stretches from the hills south of Siena to Monte Amiata, the massive volcanic lava dome near Lake Bolsena.

Pienza was rebuilt from a village called Corsignano, the birthplace of Enea Silvio Piccolomini) who became Pope Pius II in 1458 – a short papal reign as he died six years later. On becoming pope, Piccolomini had the entire village rebuilt as a Renaissance town and renamed it Pienza. He intended it to become his retreat from Rome, but did not live long enough to fully enjoy it.

From Pienza, continue another thirteen kilometres east to the Montepulciano turnoff, then follow the SP17 into town. Remember that the town centre is closed to traffic, so you will have to park your car in one of the dedicated areas on the edge of town.

Montepulciano is a Tuscan gem that sits majestically on top of a narrow, sloping limestone ridge. It’s the largest hill town in southern Tuscany and boasts several imposing palaces. Montepulciano is often described as a mini Florence, and for that reason alone is worth a visit.

The Piazza Grande, or main square, is most impressive: a medieval cathedral, clock tower and town hall –and several bustling cafes. It’s reached by following the Corso, a long winding street that leads up a steep hill from Porta al Prato, one of the town’s ancient gates.

Montepulciano -- producing exquisite wine

Montepulciano is known for the famed Vino Nobile di Montepulciano, the king of Chianti wines – which makes a visit to the town mandatory for wine lovers travelling this route. The town is not short of wine shops. Many of them let you visit their cellars, where row after row of oak barrels line the ancient walls of what were once underground tunnels connecting Montepulciano’s palaces.

You will need a more than a day to take in everything there is to see in Montepulciano and still have time to taste its wines, so if you are a wine lover it is definitely worth staying an extra night. Foodies will love market day on Thursday.

Accommodation options. Hotel Il Borghetto, Hotel Panoramic, Albergo Duomo

Day 3. Depart: Montepulciano  Arrive: Florence 175 kms

Start today’s drive by heading north to Torrita di Siena, a village that acted as a bulwark to defend Siena during its age-long medieval conflict with Florence

The castle of Torrita was protected by towered walls and gates: Porta a Gavina, Porta a Pago and Porta a Sole. Porta Nuova was opened in the 19th century. Some of the ruins still exist. Each year in March, Torrita di Siena celebrates its history with a pageant – one of the highlights of which is a donkey race.

From Torrita di Siena continue north to Sinalunga, where the Sienese defeated an English mercenary army back in the mid-1300s; then weave your way west to Rapalano Terme, a popular spa town, where the hot sulphur waters have been enjoyed for many centuries.

It’s doubtful that the drive so far has stressed you out, but you still might want to soak in the spa’s soothing waters. The resort facilities at San Giovanni Terme Rapolano include four thermal pools with varying natural temperatures. From the pools you have a breathtaking view out over the wooded hills of Crete Senesi, it means Sienese clay. If you decide to stay the night you’ll be rewarded with magnificent sunsets.

From Rapalano Terme you continue on in the direction of Siena, where you pick up the road that leads you north to Monteriggioni and Poggibonsi.

A visit to the walkways around the castle walls is not to be missed at Monteriggioni. From the heights of this defensive walkway, you get a spectacular view of the Chianti and the Val d’Elsa.regions, with their vineyards, olive groves and centuries old cypress trees. There is a small fee to make the walk around the ancient walls of Monteriggioni, worth it for the views alone.

San Gimignano -- on the old pilgrimage trail

From Poggibonsi it is easy to reach San Gimignano, a walled village located on an old route that once took pilgrims from Northern Europe to Rome. A famous feature of the village is the thirteen remaining towers that date from 1150. Like many other Tuscan towns and villages of the time, San Gimignano fell victim to many political intrigues, but it was the Black Death plague in 1348 that did the most damage. As in other parts of Tuscany, the population of San Gimignano was decimated.

It was the town’s prosperity during the days when it was on the pilgtimage route that led to its churches and monasteries being adorned with magnificent art. The ‘must see’ attractions of San Gimignano include the Collegiate Church, with its valuable Sienese School frescoes statues and sculptures; the picture gallery of the People’s Palace; the Museum of Sacred Art; and the Archeological Musum, with its Etruscan, Roman and Medieval findings from the city and the surrounding area.

You might also want to visit a local winery to taste Tuscany’s famous white wine, Vernaccia di San Gimignano.

Leaving San Gimignano, you take the SP 127 to Sant Andrea, from where you wind your way up to Ulignano and Vico d’Elsa. If you wanted to spend the night in this area there are several guesthouses and converted farms along the way.

From Vico d’Elsa head the road that leads you through Barbrino Val d’Elsa, up to San Casciano in Val di Pesa, and back to Florence.