Cycling Classic Tuscany: Florence, Chianti, Siena, Volterra & Pisa

Independent arrival · online briefing
The trip begins in the late afternoon. Upon arrival in Florence, make your own way to our selected hotel in the historic centre. You can drop off your luggage before heading out to see the sights. In the evening, we’ll hold an online briefing to go over the route, stages, and practical tips. We’ll also deliver the bikes for those who’ve chosen the rental option.

Before you set off, Florence deserves a dedicated morning. The Duomo, Piazza della Signoria, Ponte Vecchio. Don’t miss Piazzale Michelangelo either — a wonderful terrace overlooking the city. It’s a steep walk up , but the view is worth every meter.
After taking in these iconic landmarks, the ride begins. You leave the city and enter the hills of the Gallo Nero, the heart of Chianti Classico.
Rows of vines alternate with cypress trees, and villages appear and vanish behind the curves. The stage ends in Greve in Chianti, birthplace of Giovanni da Verrazzano: the navigator who in 1524 became the first European to explore the bay where New York stands today, and after whom the Verrazzano-Narrows Bridge is named.

The most demanding stage of the tour — but also the one where the legendary white gravel roads show what they’re made of. The gravel crunches under your wheels, vineyards of Chianti Classico stretch as far as the eye can see, and medieval villages and parish churches stand where they’ve stood for centuries, silent and intact. You arrive in Siena: the city of the Palio, of the black-and-white striped Duomo, of the contrade that still competes today as if time had never passed.

Before leaving Siena, you pass through Piazza del Campo and of course the Duomo. Then the route joins the Via Francigena, the ancient pilgrimage road to Rome, and crosses Monteriggioni — the fortified village that Dante immortalised in the Inferno, comparing its towering walls to the giants of the Abyss.
From there, the Via del Sale leads to Volterra: an Etruscan city, then Roman, today known worldwide for its alabaster craftsmanship. A city that lived a thousand lives before you even stepped through its gates.

The fifth stage is the longest but also the most relaxed, with the fewest climbs. From Volterra you descend gradually, passing through the calanchi — a geological phenomenon where water has carved clay over millennia, creating landscapes that seem to belong to another latitude. As you ride on, the scenery shifts. First hills, then flatland, and in the background the blue of the Mediterranean with the islands of the Tuscan Archipelago.
You arrive in Pisa, home to the famous Leaning Tower.

Piazza dei Miracoli deserves a stop before you leave: the Duomo, the Baptistery, and the Tower are symbols of the power Pisa once held. During the Middle Ages it was, along with Genoa, Amalfi, and Venice, one of the great maritime powers of the Mediterranean.
After visiting Piazza dei Miracoli, you leave the city along the bike path that runs beside the Arno river, then continue on country lanes that climb toward San Miniato. The village sits on a hill halfway between Pisa and Florence — a position that in the Middle Ages made it a battleground between the two cities, and today makes it a unique viewpoint over the plain. A detail worth knowing: San Miniato is also the Italian capital of the prized white truffle.

This is the final stage. You descend from San Miniato and reach the Arno cycling route, which runs alongside the river all the way to Florence. The city reappears exactly as you left it seven days ago. But something has shifted—and no, it isn’t the city.