Chiantigiana Wine Road (75 km)
Florence to Siena · back a different way, via Via Chiantigiana and Crete Senesi Loop
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Why this ride
75 km one way from Florence - plan on about 1 h 14 of riding. On the way it passes Greve in Chianti, Panzano and Castellina in Chianti. It suits an unhurried touring pace.
Roadbook
- Florence
start
Florence was one of the great stops on the Mille Miglia, and it is easy to see why the race came through. Drivers arriving from Bologna had crossed the Raticosa and Futa passes in the Apennines, a long, twisting run of hairpins that tested both engines and nerves, then dropped down into the Arno valley to the city where Brunelleschi's red dome rises above a sea of terracotta roofs. The dome, completed in the fifteenth century over the cathedral, was a feat of engineering that was done without a conventional wooden frame, and it still defines the skyline.
Riding into Florence from the north is a different thing from the old race. The city centre is small, dense and heavily restricted, with a ZTL traffic zone covering most of the historic core, and the camera system issues fines to anyone who enters without permission. The best plan is to leave the bike in a car park or on the outskirts, such as near Piazzale Michelangelo or in the suburbs, and walk. Cobbles and tram lines call for care, and summer heat can be fierce. The city is crowded from April to October, and the queues for the major museums, including the Uffizi and the Accademia, can be long, so book ahead.
For fuel, food and coffee, Florence has everything, and the outskirts have large petrol stations and supermarkets. Fiesole, on a hill north of the city, is a charming small town with Etruscan and Roman remains, an old cathedral and fine views back over the rooftops, and the road up to it is a pleasant short ride, with bends through cypress and olive groves. For a longer day, the roads south of the city into Chianti are among the best in Italy for relaxed riding, with gentle hills, vineyards and stone villages.
The food is robust and local. Look for bistecca alla fiorentina, a thick T-bone steak cooked rare over coals, ribollita, a bread and vegetable soup, and lampredotto, a tripe sandwich sold from street carts. Gelato was famously refined here, and the cafés still make it well.
Aim for early morning or late afternoon, when the golden light on the Arno is worth the effort.
- Greve in Chianti
scenic
Greve is the sort of town that makes you want to put the kickstand down and wander. Its heart is an odd, wedge-shaped piazza lined with arcades, with a statue of the explorer Giovanni da Verrazzano in the middle. He was born in a castle nearby, and he is remembered as the first European to sail into New York Bay. Under the porticoes are butchers, wine shops and cafes, and on market days the square fills with stalls selling cheese, sausage and local produce. It is the natural capital of Chianti, in the best sense, a working market town, not a museum.
The Chiantigiana, the old state road that runs between Florence and Siena, passes right through, and it is a classic of Tuscan riding. The bends are easy, the surface is generally good, and the landscape rolls past in a pattern of vineyards, olive groves, cypress and stone farmhouses. The black rooster, the symbol of the Chianti Classico wine league, appears on signs and bottles everywhere. It is not a road for speed, because there are too many cyclists, camper vans and rental cars, but it is a road for pleasure, especially on a weekday in spring or autumn. Summer is hot and crowded, and the light at midday is flat.
Wine is the point, and the wine of the region is made mainly from Sangiovese. In the shops of Greve you can taste Chianti Classico, from young and fruity to aged and complex, and buy bottles to take home, if you have luggage space. A plate of ribollita, the hearty Tuscan bread and vegetable soup, or a slice of bistecca alla fiorentina is a fine reward. If you are riding, a small taste is enough, and a coffee will do the rest.
Greve has everything a rider needs. There are petrol stations on the edge of town, supermarkets, banks, pharmacies and plenty of places to eat, and it is a good base for a few days in the area. Tavarnelle Val di Pesa, about twelve kilometres away, is a larger town with more services. The hills around are dotted with castles and villas, many of which offer tours and tastings.
The best times to ride the area are May to June and September to October. In October the grape harvest brings tractors and the smell of crushed fruit to the roadside, and the slopes turn gold and red.
- Panzano
scenic
Panzano sits on a ridge above a natural amphitheatre of vineyards that the locals call the Conca d'Oro, the golden shell, and the name is not an exaggeration. The terraces face south and catch the sun from morning to evening, and the wine grown on them is among the most respected in Chianti. The village itself is small, with a single main street, a ruined castle, a church and a handful of shops, but it has the confident air of a place that knows its worth. The views from the edge of the village across the valley are some of the best in Tuscany.
Panzano is also famous for meat. It is home to a butcher who became a celebrity, known for reciting passages from Dante to his customers while he cuts, and for turning the shop into a kind of theatre, with long tables, wine and platters of cured and cooked meat. Whatever you think of the performance, the quality is high, and Tuscan beef is a serious business. If you arrive at the right time, you can eat very well in the village, and there are other restaurants and wine bars serving local dishes.
The riding here is a delight. The Chiantigiana runs along the ridge, with long, easy bends and views on both sides, and the side roads that drop into the valleys are narrow and quiet. Some of them turn to white gravel, and a road bike may prefer to keep to the tarmac. The surface is generally decent but can be patchy after winter, and the traffic includes plenty of tourists, so the best times are early morning and weekdays. In spring, the hills are green and the broom is in flower, and in autumn the vineyards turn to gold and rust.
For fuel, Greve in Chianti, about four and a half kilometres to the north, has stations and shops, and Tavarnelle Val di Pesa, about twelve kilometres away, offers more choice. Panzano has a few shops and a bakery, but it is best to fill before arriving. Parking is easy at the edge of the village, and a short walk takes you to the main street.
The village hosts a few events during the year, and the church of San Leolino, a Romanesque building a short way out of town, is worth a quiet visit if you want a change from the wine.
- Castellina in Chianti
scenic
Castellina in Chianti is a fortress town that once guarded a frontier. In the Middle Ages, the hills between Florence and Siena were the front line of a long rivalry, and Castellina was on the Florentine side, with a stout castle built to watch the enemy. The fortress, the Rocca, still stands in the centre of the village, and part of it is now a small museum. Nearby is a covered street, the Via delle Volte, which runs under arches along the old walls and feels like a medieval alley, with cool air and stone vaults overhead. The town was one of the three original members of the Chianti League, a military and political alliance of the fourteenth century that gave the region its name.
The history goes back much further than the Middle Ages. Just outside the town is an Etruscan burial mound, a reminder that people were living on these ridges long before Florence or Siena existed. The museum in the Rocca has finds from the area, and the landscape of vines and olives has been farmed for thousands of years. The wine is the heart of the local economy, with Chianti Classico produced by the estates all around.
For a rider, the ride to Castellina is a classic. The Chiantigiana, the state road between Florence and Siena, runs through the town, with easy bends and long views across the vineyards. The surface is generally good and the gradients are gentle, but the road can be busy with traffic, especially at weekends and in high summer, so weekdays are better. On the side roads, you will find narrow lanes and gravel tracks, with farmhouses and cypress avenues. Spring and autumn are the best seasons, with soft light and green or golden hills.
Castellina has several wine shops, cafes and restaurants, and the food is typical of the region, with Tuscan bread, pasta with boar sauce, and grilled meats. It is a good place for a leisurely lunch, with plenty of choice. For fuel, there is a station on the main road in the area, but it is wise to fill in larger towns such as Poggibonsi, about eleven kilometres away, where you will find more services and supermarkets.
On the way south towards Siena, the road passes some of the most beautiful stretches of the Chianti, with the vines in neat rows and the old stone houses sitting in the folds of the hills. Take it slowly and enjoy it.
- Siena
finish
Siena is the opposite of Florence in nearly every way that matters, and the Sienese would like you to remember it. It sits on three ridges in southern Tuscany, a compact medieval city of brick and stone in warm reddish-brown tones, and at its centre lies the Piazza del Campo, a vast shell-shaped square sloping down to a tall brick tower, the Torre del Mangia, about a hundred metres high. Twice each summer, on the second of July and the sixteenth of August, the square is covered with earth and ten riders from the city's districts, the contrade, race bareback around it in the Palio, a dangerous, chaotic event that lasts about ninety seconds and is felt by the whole city as a matter of honour.
The seventeen contrade, each with its own emblem, colours and fountain, dominate local life, and you will see their flags hanging in the streets. The cathedral, made of striped black and white marble, has a floor of inlaid scenes and a library of painted manuscripts that dazzles. The city was a rival to Florence in the Middle Ages, a banking power and home to its own school of painting, and its bank, Monte dei Paschi, founded in 1472, claims to be the oldest in the world still operating. Local food includes panforte, a dense spiced cake, and ricciarelli, soft almond biscuits.
For riders, Siena is the starting point for a famous scenic ride. South of the city, the roads wind through the Crete Senesi, a landscape of pale clay hills, and then into the Val d'Orcia, a UNESCO site of rolling fields, cypress-lined lanes and hilltop towns such as Pienza and Montalcino. Surfaces are generally good, with gentle curves and wide views, and the white gravel roads, strade bianche, add some adventure for those who like it. Spring, when the fields are green, and late September, when the grapes are ripe, are the best times. July and August are hot, and tourist traffic is heavy.
Be careful in the old city, because much of it is a restricted traffic zone where unauthorised vehicles can be fined by camera, so park outside the walls and walk in. Fuel stations and workshops are on the ring roads, and plenty of cafés and trattorias are in the historic centre. Stay for sunset in the Campo, when the brick turns gold.