Distance: 40–50 km (depending on the chosen loop)

After checking in at the hotel, it’s time to start pedaling and get a first taste of the city and its surroundings. From the center of Pisa, ride along the Lungarni, crossing bridges with stunning views over the Arno River. Before leaving the city, make a quick stop at Piazza dei Miracoli to greet the famous Leaning Tower.

From here, the route continues towards San Giuliano Terme, along flat and smooth secondary roads with views of the Pisan Mountains. You can extend the ride to the village of Asciano Pisano or, for a few more kilometers, reach Calci to admire the splendid Charterhouse Monastery.

The loop back to Pisa takes you past the famous mural by Keith Haring “Tuttomondo” and through the greenery of the Giardino Scotto.

A ride that combines history, art and natural landscapes, perfect as a warm-up for the coming days. To close the evening, enjoy dinner in a typical Tuscan trattoria with local specialties such as “cecina”, tagliolini with cuttlefish ink or a hearty Pisan soup.

Distance: 60–70 km (with optional loops along the Monti Pisani)
From the center of Pisa, the ride begins along the route of the ancient Medici Aqueduct, an extraordinary hydraulic work built in the 17th century by order of Ferdinando I de’ Medici. The route partly follows the “Giacomo Puccini” cycle path, running beside the arches of the aqueduct and winding through farmland and rural villages.

Continuing towards the Monti Pisani, the road becomes slightly rolling and offers spectacular views over the valley. The itinerary leads to the historic Rocca di Ripafratta, with its ancient border towers between Pisa and Lucca, before reaching the banks of the Serchio River.

The final stretch brings you directly to the imposing medieval walls of Lucca: here you can either ride a full lap on top of the walls, admiring the city from above, or descend straight into the cobbled streets and lively squares of the center. A stop in the old taverns is a must: traditional Lucchese dishes, soups, farro, and excellent local wines.

Distance: 80–90 km
Elevation gain: approx. 600 m

The ride starts from the walls of Lucca, following the scenic Via delle Ville Lucchesi, lined with Renaissance villas and quiet country roads. The route continues to Montecarlo, a medieval village famous for wine and olive oil, once an important stop for pilgrims on their way to Rome.

From there, descend towards Altopascio, where it’s worth stopping to taste the renowned Altopascio bread, perfect with local cold cuts. A break at the foot of the Bell Tower takes you back to medieval times: its chimes and the fire lit on top once guided pilgrims along the Via Francigena.

Leaving Altopascio, the road opens up to one of the most evocative sections of the journey: the original cobblestones of the Via Francigena, crossing the wild Cerbaie woodlands. After crossing the Arno River, the final stretch leads to San Miniato, with its magnificent Seminary overlooking the main square.

End the day with a well-deserved dish of tagliatelle with white truffle, the pride of San Miniato’s cuisine, while enjoying the sunset over the hills.

Distance: 70–80 km
Elevation gain: approx. 900 m

One of the most spectacular stages of the journey, demanding but full of unforgettable landscapes. From San Miniato, the route descends into the Val d’Elsa, riding among vineyards and rolling hills, before climbing secondary roads towards Gambassi Terme. Here, it’s worth visiting the thousand-year-old Pieve di Chianni or taking a regenerating break at the thermal baths, surrounded by a park of centuries-old trees.

The ride continues through the authentic Tuscan countryside, with constant ups and downs that challenge the legs but reward you with breathtaking views. The arrival in San Gimignano is an unforgettable moment: the famous medieval towers rise on the horizon, creating one of the most iconic skylines in Italy.

Inside the walls, don’t miss the climb up the Torre Grossa for a view over the city and the surrounding hills. And if you still have energy, head to the Rocca di Montestaffoli for an even more special panorama at sunset.

Distance: 80–90 km
Elevation gain: approx. 1,200 m

Leaving San Gimignano, the road winds through the Tuscan hills in a continuous series of ups and downs that test the legs but reward you with postcard landscapes. After a few panoramic stretches among vineyards and olive groves, you reach Colle Val d’Elsa, with its old town enclosed by stone walls and narrow alleys that take you back in time.

Continuing along secondary and scenic roads, you’ll ride through one of the most beautiful sections of the Via Francigena. The sight of Monteriggioni Castle, with its crown of medieval towers perched on the hill, is one of the highlights of the journey. A stop on its walls is well worth it, offering breathtaking views over the surrounding countryside.

The final stretch leads towards Siena, alternating gentle hills with more demanding climbs. Entry into the city takes place through Porta Camollia, the traditional Francigena gateway to the historic center.

The day ends in the heart of Piazza del Campo, enjoying a typical dish of pici pasta with wild boar ragù or with aglione sauce, in front of one of Italy’s most iconic settings.

Distance: 75–85 km
Elevation gain: approx. 1,200 m

Leaving Siena, the route heads north into the fascinating Crete Senesi. Barren, rolling hills stretch as far as the eye can see, dotted with isolated farmhouses and rows of cypress trees. Thanks to the clay soil, the landscape sometimes takes on grey-blue shades, giving it a lunar feel.

The ride continues on quiet paved roads, passing through characteristic villages such as Asciano and Castelnuovo Berardenga, before entering the heart of the Chianti Classico. Here, the scenery changes completely: hills covered with vineyards, olive groves and woods create a unique palette, to be enjoyed turn after turn.

Before reaching the destination, a stop at the majestic Castle of Brolio is a must: for centuries a symbol of Chianti winemaking and a perfect spot for panoramic views.

The stage ends in Radda in Chianti, a medieval village still surrounded by walls, with cobbled streets and wine cellars inviting you to celebrate the day with a glass of local wine.

Distance: 85–95 km
Elevation gain: approx. 1,100 m

The final stage crosses the heart of the Chianti Classico, among rolling hills covered with Sangiovese vineyards. The ride heads towards Panzano in Chianti, a charming village that hosts one of the area’s most famous stops: the butcher shop of Dario Cecchini, the “poet of steak.” A stop here is almost a ritual: top-quality cold cuts and meat, and for those with time and appetite, the legendary Florentine steak (reservation required).

Continue towards Greve in Chianti, the capital of Florentine Chianti, with its Renaissance square and lively market-town atmosphere. Between wine shops, artisan stores, and local producers, Greve showcases the true soul of the region.

The last stretch follows a splendid panoramic road descending into Florence: a triumphant entrance and the perfect conclusion to a unique journey through history, culture, and breathtaking landscapes.

And here, there’s no need to list what to see: one extra day is always well spent, two even better.