Chianti by Motorcycle: The Chiantigiana (SR222) from Florence to Siena

The Chiantigiana is the road through the heart of Chianti, the wine country between Florence and Siena. Officially the SR222, it runs for about 70 kilometres from the edge of Florence to Siena, along ridges and through valleys covered with vineyards, olive groves, oak woods and lines of cypress trees. It is not a fast or demanding road; it is a beautiful one, with bend after bend and a wine village every few kilometres. Ride it south, come back through the eastern Chianti hills, and you have one of the classic days in Tuscany.

Planning the ride

Greve in Chianti, halfway along the road, is the most convenient base, with Radda and Castellina as smaller, quieter alternatives. Florence and Siena are wonderful cities but not easy places to keep a bike: both have strict limited traffic zones (ZTL), and riding into one without a permit means a fine by camera. Stay outside the centres and ride in only to park in the designated motorcycle areas.

Most riders reach Tuscany on the A1 motorway from Bologna, crossing the Apennines. If you have time, the old SS65 over the Futa pass between Bologna and Florence is a far better ride than the motorway, and the Raticosa pass alongside it is a favourite of Bologna's riders.

The Chiantigiana (about 70km)

Florence to Greve (about 25km). Leave Florence from the south-east, through Grassina, and pick up the SR222 heading south. The suburbs give way to hills within a few kilometres. The road climbs over a series of ridges through Strada in Chianti, with the first vineyards and the first wide views, before dropping to Greve. Greve's triangular, arcaded piazza is the classic coffee stop.

Greve to Panzano and Castellina (about 20km). South of Greve, the road climbs in a run of bends to Panzano, a hilltop village with views over the Conca d'Oro, the "golden basin" of vineyards below it. From Panzano it continues along the ridge to Castellina in Chianti, past wine estates and medieval villas. This is the best riding on the Chiantigiana: well surfaced, with flowing bends and long views on both sides.

Castellina to Siena (about 25km). The last section drops south past the hamlet of Fonterutoli toward Siena, with fewer villages and longer sweeping bends. Siena's Piazza del Campo, the shell-shaped square of the Palio horse race, is a short walk from the parking areas outside the walls.

The return loop through eastern Chianti (about 120km)

Siena to Brolio (about 25km). Ride north-east from Siena into the eastern Chianti hills toward Castello di Brolio, the castle of the Ricasoli family, where the modern recipe for Chianti wine was written in the 19th century. The road to it winds through vineyards and woods.

Brolio to Gaiole and Radda (about 25km). From Brolio ride north to Gaiole in Chianti and climb west to Radda, a walled village on a ridge. The roads between them are narrower and quieter than the Chiantigiana, with tighter bends and more woods, and they are some of the best small roads in Tuscany.

Radda back to Greve or Florence (about 70km). From Radda, ride west to rejoin the SR222 near Castellina, or north through the hills and back to Greve, then return to Florence along the Chiantigiana or the parallel roads through the Val di Pesa.

Extension: the Val d'Orcia

South of Siena, the Val d'Orcia is the Tuscany of postcards: rolling hills of wheat, lone cypress trees and hill towns such as San Quirico d'Orcia, Pienza, Montalcino and Montepulciano. The SR2, the old Via Cassia, runs south from Siena through the valley, and the small roads between the towns are excellent. It makes a full second day.

The roads

Surfaces on the SR222 are generally good, but the minor roads can be patched and bumpy, and some of the most scenic links between villages are white gravel roads (strade bianche): avoid them on a heavy road bike. Traffic is light on weekdays and heavier on summer weekends, with tourists stopping suddenly at viewpoints and wine estates. Cyclists are everywhere in spring and autumn. Watch for wild boar at dusk.

In Italy, motorcycles must ride with dipped headlights on at all times. Limits are generally 50km/h in towns and 90km/h on country roads. Italian motorways are tolled. See our riding in Italy page for more on the rules, including ZTL zones.

When to go

April to June and September to October. Spring brings green hills and wild flowers; autumn brings the grape harvest and the woods turning gold. July and August are hot and busy, and the afternoons are best spent in the shade.

Food and wine stops

Chianti is wine country first. The black rooster on the bottle neck marks Chianti Classico, made in the hills between Florence and Siena, and nearly every village along the Chiantigiana has a wine shop (enoteca) where you can taste, and estates that will ship a case home so it does not have to ride in your panniers. Since you are riding, the sensible plan is to taste at the end of the day, with the bike parked. Tuscan food is simple and generous: ribollita (bread and vegetable soup), pici pasta, pecorino cheese and the huge T-bone steak known as bistecca alla fiorentina.

A suggested day

Leave Florence early and ride the Chiantigiana south while it is still cool, with a coffee in Greve and a stop for the view at Panzano. Have lunch in Castellina, then ride into Siena in the early afternoon, park outside the walls and walk to the Campo. Return north in the late afternoon by Brolio, Gaiole and Radda, when the light is low and gold over the vineyards, and you will understand why the road is famous.

Where to stay

Greve, Radda and Castellina are the best bases for the Chianti roads; Siena suits riders who want a city in the evening, with a hotel outside the ZTL. Many agriturismi (farm stays) in Chianti have space to park a bike inside the grounds. See our Italy biker hotels. For the Alps and the north, see the Lake Garda guide and the best motorcycle roads in Italy.