Chianti: itinerary from Florence to Siena

Itinerary from Florence to Siena through the Chianti and Val di Pesa.

Chianti and Crete senesi tuscany itinerary caberg levo road bmw
Chianti - Ph. Catherina Unger

From wine to the most famous landscapes in the world, Chianti has always been one of the lands where riding a motorbike is always a different emotion.

Chianti, the heart of Tuscany, is the hilly area between Florence and Siena (our itinerary), between Arezzo and the Pisan hills. A real succession of splendid landscapes among vineyards, woods, medieval villages and charming farmhouses.

Content index

  1. Florence and the American cemetery
  2. The Val di Pesa
  3. Sambuca and San Donato
  4. Castellina in Chianti
  5. Siena
  6. Where to sleep and eat
  7. Map and information

Our itinerario is an alternative to the parallel “Strada del Chianti (or via Chianti area) ”, But no less beautiful, indeed, it offers you the opportunity to discover many other things along the way.

Chianti and Crete senesi tuscany itinerary caberg levo road bmw
The curves of Chianti - Caberg Levo helmet

Florence and the American cemetery

A city that has kept its charm and the splendor of the past unaltered. Firenze, capital of the Toscana is the starting point of our tour. An enchanting city that never ceases to surprise, with its works of art, churches and architecture that recall its role in the development of Renaissance art and culture.

American Cemetery of Florence Chianti tuscany itinerary caberg levo road bmw
American Cemetery of Florence - Ph. S. Venturi

A few kilometers south of Florence you can visit the American Cemetery, where 4.402 young soldiers of the 5th Army who died during the Italian campaign between 1943 and 1945 are buried. A place that deserves a brief stop and a thought for those who paid with their lives for the liberation of our nation.

The Val di Pesa

One of the villages best known of the Val di Pesa is San Casciano, the first town in Chianti that you meet starting from the north. Among the monuments to visit we find the Collegiate church and Church of Mercy, Parish church of Santa Cecilia in Decimo; The Romanesque parish church of San Giovanni in Sugana; The Parish church of San Pancrazio and Parish church of Santo Stefano in Campoli, near Mercatale Val di Pesa.

Sambuca and San Donato

Even the village of Sambuca it is located in Val di Pesa. The town takes its name from the castle of Sambuca, formerly placed on the top of the hill in a strategic position. Around 1100, the Bridge of Romagliano at the foot of the castle of Sambuca, already before the XNUMXth century, to allow the crossing of the river Pesa alla Via per Siena and Rome.

San Donato in Poggio -Chianti and Crete senesi tuscany itinerary caberg levo road bmw
San Donato in Poggio - Ph. F. Capone

From here, along the SP101, we stop quickly at San Donato in Poggio. One of the main entrances to the city is through the "Porta Fiorentina“, From which you enter the main road, via del Giglio. In the small village the Palazzo Malaspina and Palazzo Pretorio are worth visiting, in addition to the splendid one Parish church of San Donato, in Romanesque-Tuscan style.

Castellina in Chianti

With Greve in Chianti, the Via Chiantigiana opens up in countless possible detours and itinerary ideas. TO Castellina in Chianti you can visit two important archaeological sites of the Etruscan period: the Tumulus of Montecalvario and Necropolis of Poggino.

Chianti and Crete senesi tuscany itinerary caberg levo road bmw
Chianti and Crete Senesi - Ph. F. Capone


Siena it is at the end of our itinerary, also because it really deserves at least a full day to be discovered. Here time seems to have stopped at the thirteenth century, when the city began to enrich itself with a artistic and architectural heritage who has consecrated its glory forever. Unesco defined it "a masterpiece of dedication and inventiveness in which the buildings have been designed to be adapted to the entire design of the urban structure".

Famous for the Palio in Piazza del Campo, Siena is also:  Sansedoni Palace, Palazzo Pubblico, Torre del Mangia which dates back to the forties of the fourteenth century; the Duomo and the Piazza Chapel. Moving on to the churches, the splendid ones are absolutely worth visiting San Domenico e Santa Maria dei Servi.

Where to sleep and eat


For this itinerary we used: Caberg Levo helmet - Motorcycle BMW R1200RS - Intercom Sena SF4 - SW-Motech Bags

Map and information