Day 1: Arrival in Pienza
Your adventure in Tuscany will begin in Pienza. Although Pienza is a UNESCO World Heritage Site and a fantastic Tuscan destination, it’s not on a train line. The closest, best-served train station is in Chiusi, which is 35 km from Pienza on the Rome-Florence line. Bus connections are possible but confusing; we highly suggest hiring a cab to take you to the former 15th century convent where you’ll be staying. Afterwards, you’ll meet your local guide who will outfit you with bikes and go over your itinerary. If you have time, you can explore this carefully-planned Renaissance town, designed to be a “utopia” by Pope Pius II. You can visit his home, Palazzo Piccolomini, which is located near the town’s Duomo.
Day 2: Loop from Pienza through Montepulciano - 50 km (31 miles)
Have you ever seen a movie set in Tuscany and dreamed of visiting scenic landscapes dotted with vineyards, cypresses, and enchanting villages? Today’s route will take you through the countryside where The English Patient was filmed. You’ll first ride through the hilltop village of Castelmuzio, where you’ll be greeted by the tower of Palazzo Fratini. The next hilltop village is Montepulciano - we recommend a stop at the top for lunch and maybe a glass of the famous Vino Nobile di Montepulciano wine. It’s also home to some interesting religious buildings, if you want to take a peek. Last but not least (and who could get sick of Tuscan scenery?), you’ll ride through yet another hilltop village, Monticchiello, before returning to Pienza.
Day 3: Pienza to Montalcino - 46 km (29 miles)
Though we don’t recommend a bath, we invite you to imagine Romans relaxing in Bagno Vignoni, a thermal spa town which is on today’s itinerary. Beautiful Castiglione d’Orcia comes soon after. In the center of the stone-paved town, the Piazza il Vecchietta offers a great place to rest and soak in the scene; you could also visit castle ruins, like the Rocco Aldobrandesca. Definitely visit the Abbey Sant’Antimo, because pictures hardly do it justice. If you’re timing’s right, you may even hear Gregorian chanting through the monastery walls. When you reach Montalcino, your destination for the evening, we know you’ll enjoy a satisfying Italian dinner – and it might pair well with the famous local wine, Brunello.
Day 4: Montalcino to Siena - 60 km (37.5 miles)
Every turn today will take you through picture-perfect Tuscan scenery. Following a picturesque crest road, you’ll ride by the Monte Oliveto Maggiore monastery, an impressive red brick building where you may also hear the beautiful chants sung by the monks. Enjoy the atmosphere while lunching before cycling on to Siena. Make the best of your afternoon and explore its countless treasures such as its unfinished Duomo and its famous Piazza del Campo where the Palio horse race is held twice a year.
Day 5: Siena to Castellina-in-Chianti – 45 km (or 28 miles)
For every hill we have in store for you today, there’s also a fantastic “recovery site” for a little rest. First you have medieval Castelnuovo Berardenga, with castle ruins to visit and handsome villas to view. This town’s also the gateway to the region where Chianti, the famous Italian wine, is produced. If you’re up for a wine tasting, continue on to the impressive fortress of Castello di Brolio. Your destination is Castellina in Chianti, home to a few pretty palazzos and a massive castle (Rocca), which also houses a small Etruscan museum.
Day 6: Castellina to San Gimignano - 60 km (37.5 miles)
On the road, you’ll ride through the well-preserved time capsule town of Monteriggioni – except for some work in the 16th Century, no one’s made any changes to the walls or buildings since their construction! Stop also to admire the view of your final destination in the distance: you can’t miss that distinctive skyline of stone towers. San Gimignano is exceptional (it’s a UNESCO World Heritage site), and we cannot recommend enough that you arrive early to ensure a thorough discovery this fascinating place. May we suggest climbing the Torre Grossa for unobstructed views? Down on terra firma, you can find a number of unbelievable restaurants set in historic buildings that your taste buds are sure to remember for years to come.
Day 7: Departure
After breakfast, depart San Gimignano at the time of your choice. You may also opt to ride a short route that will take you to Certaldo (worth a visit) where you’ll hop on a train to Florence (a 50 minutes’ ride).