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Brunelleschi's dome and the marble-clad drum of Florence Cathedral framed by shadowed buildings, portrait

Tuscany Motorcycle Tour

Hill towns, cypress roads, and dinners that run late.

Florence to Siena on the Chiantigiana, sixty-nine kilometres that never quite straighten. South into the Val d'Orcia, a landscape planted as a view five hundred years ago. Montalcino, Pienza, San Gimignano. A pass into the Casentino forest where the first uphill motorcycle race is said to have been run in 1903. Departures announced soon.

What are the best motorcycle roads in Tuscany?

The SR222, the Chiantigiana, from Florence through Greve, Panzano, Castellina, Radda, and Gaiole to Siena: sixty-nine kilometres of vineyard and castle road, two hours without stops. The SP146 through the Val d'Orcia between San Quirico and Pienza, the cypress-lined stretch in every photograph. And the SR70 over the Passo della Consuma at 1,059 metres into the Casentino, forest instead of vines, and the emptiest riding in the region.

Narrow wet cobblestone lane between ochre palazzi at dusk with bicycles and potted plants, a cyclist in the distance; textbook Florence side-street
Ponte Vecchio over the green Arno in daylight with hills and further bridges beyond; landscape frame

What is the best month to ride in Tuscany?

May, when the hills are green, or September, when they have gone to gold. Both are warm without being punishing and the roads are manageable. August is the month to avoid on every count: highs of thirty to thirty-five degrees, the heaviest traffic of the year, and Ferragosto shutting the restaurants. Siena's Palio, on 2 July and 16 August, fills the city and empties the hotels for a week either side.

The view was landscaped on purpose, in the fifteenth century.

The Val d'Orcia is a UNESCO site because it was designed. The Sienese families who owned it in the Renaissance planted the cypresses and placed the farms to make a picture of good government as much as a working estate, and the picture is what a rider sees from the SP146 today. Pienza, on the ridge above it, was the village of Corsignano until 1459, when a pope born there had it rebuilt as an ideal city in three years.

Dinner is a steak measured in fingers.

Bistecca alla fiorentina: bone-in loin from Chianina cattle, cut four to six centimetres thick, a kilo or more, and sold by weight. Pici, the hand-rolled flour-and-water pasta of Siena, called pinci around Montalcino. Pecorino from Pienza. Brunello di Montalcino, first made by the Biondi-Santi family in 1888 and among the first wines in Italy given the top classification in 1980, and Vino Nobile from Montepulciano, twenty kilometres away and not the same wine.

San Gimignano's skyline is what is left of one.

Fourteen towers stand of the seventy-two the town's families built to outdo each other in the thirteenth century. The tallest, the Torre Grossa, was begun in 1300 and took eleven years. The town has been a UNESCO site since 1990 and the towers are visible from the road long before the walls are. Across in Bologna, an hour and a half north of Florence, the Motor Valley has a museum at the Ducati factory and the Mugello circuit that Ferrari has owned since 1988.

Ponte Vecchio over the green Arno in daylight with hills and further bridges beyond; landscape frame

The nights are in castles and estates that have stood for a thousand years.

Castello di Casole, a tenth-century castle on four thousand acres. Castello del Nero in Chianti, twelfth century, with a starred kitchen. Borgo San Felice, a whole hamlet near Siena. The Rosewood at Castiglion del Bosco in Montalcino, where the restaurant holds two stars. In Florence, the Four Seasons in the largest private garden in the city, and Enoteca Pinchiorri, three stars since 2004. The Harley-Davidson is waiting at the first hotel.

What riders ask about Tuscany.

Whether the white gravel roads suit a Harley, whether the Ducati factory is on the route, and what happens to Italy in the middle of August. Three short answers.

Are the famous white roads rideable on a Harley?

Some of them, slowly. The strade bianche of the Crete Senesi south of Siena are white clay gravel, and several of the postcard cypress avenues sit on them rather than on the paved road. The itinerary says which are on the route. The paved SP146 between San Quirico and Pienza is the one in most of the photographs.

Does the tour visit the Ducati factory?

Borgo Panigale is in Bologna, across the border in Emilia-Romagna, an easy day from northern Tuscany along with the Mugello circuit. Whether a departure includes it, and whether the museum is open that week, is on the itinerary. The museum closed for renovation for part of 2026.

What is Ferragosto?

The 15th of August, when Italy closes. Restaurants, shops, and family businesses shut for the days around it, often from the 1st to the 20th, and the roads fill with everyone else. Tuscany in August is also thirty degrees in the shade. May and September are the months.

The other rides, and the experience.

Patagonia, Northern Thailand, the Dolomites, and Tuscany, each with its own page, and the page on the days, the hotels, the meals, and the motorcycle.

Join the interest list.

Argentina, Thailand, or Italy. Say which.