From Pisa to the heart of Tuscany

This route includes some stretches on dirt road and is thus suitable for gravel bikes yet also achievable on road bikes for riders familiar with dirt roads. The 1-day ride is recommended for well-trained cyclists, but nothing is stopping you from breaking the route into two stages and making it doable for nearly everyone.

Set out from Piazza dei Miracoli and leave Pisa, heading east toward Pontedera. The first 12.5 miles (20 kilometers) are flat. There might be some traffic as you head out of the city then you can enjoy the small, quiet country roads.

Over the next 12.5 miles or 20 kilometers, you face 5 climbs with elevation gains of between 37 and 56 miles (60 and 90 meters), with a few hard climbs. This is particularly so on the lead-up to Lari, a small village perched around its castle, certainly worth a short visit and perhaps a restorative stop in the quaint municipal piazza. At about the Kilometer 52 mark (after 32 miles), you’ll go by the village of Villa Saletta, where the large manor house, peasant dwellings, churches and squares provide a fine example of a historic Tuscan estate. At the 58ᵗʰ kilometer mark (after 36 miles), the village of Palaia preserves some of its medieval character and is well worth a ‘digression.’ From the remains of the fortress, the view will take your breath away, while just outside the village is the imposing Romanesque San Martino Parish Church, with its stone façade and the rest entirely in terracotta. Having finished exploring, get back on the trail and, once past Montefoscoli, brave the steep descent to the valley floor.

At the 70ᵗʰ kilometer mark (after 43 miles), a new climb awaits you—the longest of the day at about 8 miles or 13 kilometers. During the ascent, you will be able to make two stops for refreshments, visiting the village of Castelfalfi and the hamlet of San Vivaldo where, in the monastery of the same name, stands the interesting Sacro Monte complex boasting 17 chapels containing extraordinary polychrome terracotta sculptural groups depicting moments from biblical tradition.

Shortly after San Vivaldo, reach the highest point of the trail, at an elevation of 336 miles or 540 meters. From here, begin your descent, interspersed with a few short climbs, including one leading to San Gimignano, a village that needs no introduction and is certainly worth a stop. Continue downhill to the valley floor of the Foci stream. From here, the last climb of the day begins, taking you over a 460-feet (140-meter) drop just before Colle Val d’Elsa, another village whose historic heart is certainly worth checking out. On this route, you may prefer to bypass the village with a few miles of dirt road in order to avoid traffic. The last stretch is a zigzag of ups and downs, revealing from afar the iconic silhouette of Monteriggioni, where your adventure ends.

This route is part of the project Strade Zitte (Silent Roads), a name inspired by a song by Paolo Conte. These are “collector’s routes” for quality cycling tourism along secondary country and mountain roads, away from the rev of engines. See details on the www.turbolento.net website.