Secrets of San Gimignano Self-Guided Cycling

Option: 1

Today it's a downhill whizz out of hilltop Volterra and into the pretty Era Valley where spectacular views of the surrounding timeless Tuscan countryside open up as you pedal. After climbing out of the valley, you'll soon pass through the pretty hamlet of Castagno where we suggest a well-deserved coffee stop in the local bar. Your route continues on to Gambassi Terme, a well-preserved spa town with cobbled streets, 12th century church and lovely shaded gardens. Lunch here perhaps in one of the many trattorie then, soon after leaving the town, you'll pick up the famous Via Francigena for the gentle, mainly downhill stretch to mediaeval Certaldo where you can stop for a gelato before your final climb through olive groves and vineyards to the hamlet of Pancole. (Staying at Hotel Certaldo)

Option: 2

Distance - 75.4km (elevation +1036m / -1238m)

Leaving Volterra you drop down into the valley heading north passing the Theatre of Silence and the family home of Andrea Bocceli. Ride past rich green meadows, before climbing through the stunning countryside and on to the pretty spa town of Gambassi Terme. A long downhill ride lets you roll into Certaldo before a short climb to the peaceful Hotel Le Renaie for the next two nights.

Option: 1

Today's route explores the panoramic wine country between Pancole and Colle di Val d'Elsa. You'll first retrace your route to Certaldo and then follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities - don't forget, we can collect any purchases for you! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished 15th century fortress. The day ends with gentle pedalling through tree-lined meadows and a valley of poppy and sunflower fields to Colle di Val d'Elsa. (Staying at Relais Della Rovere)

Option: 2

Distance - 91.9km, elevation: +1521m / -1616m

Today you head into wine country on a beautiful ride with vines as far as the eye can see and passing through beautiful hamlets and interesting wine towns. With the climbing over you pass two of the famous Chianti towns, Castellina and Radda, both offering great wine tasting chances and good restaurants. Heading down to the valley you pass the stunning walled village of Monteriggioni before heading on to Colle Val d’Elsa for your next two nights.

Option: 1

It's easy pedalling this morning as you head south past the old town of Colle di Val d'Elsa, gradually climbing up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning views from its hilltop position. Take time to explore its 12th century church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps, in the lovely piazza. You then wind north, gently uphill, through wonderfully scenic countryside against the backdrop of the impressive mediaeval towers of San Gimignano as you pedal on to Pescille. (Staying at Hotel Pescille, Breakfast at the hotel)

Option: 2

Distance - 87.4km, elevation: +1693m / -1542m

Heading to the south of the region today you are rewarded with beautiful scenery, quiet roads with vistas of mountains and hills as you pass pleasant meadows, small forests and lines of cyprus trees. You pass small villages and towns that are well off the beaten track. Maybe take a late lunch in walled Casole d’ Elsa, then pass Castel San Gimignano and finish through the vines to Hotel Pescille for the next two nights.

Option: 1

It's a short ride to San Gimignano today before a climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers. Enjoy the 16km, mainly downhill run into the Era Valley. There's a real sense of achievement on your final climb through open countryside and you'll enjoy spectacular views before heading back to the ancient cobbled streets of Volterra. (Staying at Park Hotel Le Fonti)

Option: 2

Distance - 59.4km, elevation: +1078m / -943m

From the hotel you head towards San Gimignano, circling the 'town of towers' for 360 degree views and passing through the surrounding wine country. Head uphill through the vineyards and then enjoy a long downhill route with views of Volterra. Finishing with a climb into Volterra, pass through the town and ride back to your hotel for the last night.