Bicycle Tours in Italy: Cycling Classic Tuscany Tour Itinerary

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Day 1: Our Cycling Tour begins in Greve in Chianti

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Highlights: Bike fittings and introductory dinner in Greve in Chianti
We meet in Greve in Chianti today. Greve is the heart of the Chianti region, surrounded by rolling hills covered with beautiful vineyards and olive groves. We'll fit bicycles this afternoon and you can go out for a quick ride if you'd like. We have introductions and will enjoy an inaugural dinner together this evening in a local trattoria.

Day 2: Bicycle the Chianti Hills

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Highlights: Greve in Chianti to Badia a Coltibuono, wine tasting
We leave after a brief safety meeting this morning to bicycle through the vineyards of Chianti. We'll cycle along the valley of the Greve River and to the Badia a Coltibuono, famous for its monastery and vineyards, built and planted by monks in 1051 (the name in fact means "abbey of the good harvest!"). Our ride back to Greve takes us through Radda in Chianti, one of they typical towns in the region famous for its wineries and vineyards. Dinner is on your own tonight after a wine tasting of the local Chianti wines. Distance: 83 km (52 miles)

Day 3: Bicycle Greve in Chianti to San Gimignano

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Highlights: Castellina in Chianti and San Gimignano
Our first stop today is Castellina in Chianti, perhaps the most famous town in the region. Stroll around town and/or visit the fortress before beginning a long downhill bike ride out of the Chianti Hills into the valley of the Elsa River ("Val d'Elsa" in Italian). A loop along the river valley and adjacent hills then takes us up to San Gimignano, one of the best preserved medieval villages in Italy. You can pick up picnic supplies in Poggibonsi and enjoy a view back on the Chianti hills under a shade tree while you eat. We'll be in delightful San Gimignano for two nights where we have dinner together this evening. Distance: 70 km (44 miles).

Day 4: Rest day in San Gimignano

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Highlights: Alternative Bike Ride to Certaldo where Boccaccio lived or take a rest day
You can plan to spend the day exploring San Gimignano, famous for its many towers (used to be more than 100 in this small center) and people-watching, or take a ride to Certaldo, where Boccaccio, one of Italy's most famous writers, spent the last years of his life. Enjoy Certaldo's red-bricked architecture before returning to San Gimignano. Dinner is on your own this evening in one of the several local restaurants. Distance: 0-26 km (0-16 miles).

Day 5: Bicycle from San Gimignano to Volterra

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Highlights: Sightseeing in Volterra, Etruscan museum, Roman ruins
We cycle west today to Volterra, one of Italy's most famous Etruscan towns, also famous for its alabaster. Those who wish can bicycle into the rugged hills of southern Tuscany while the rest of us arrive in Volterra for some sightseeing. You'll want to visit the Etruscan museum and both the Etruscan and Roman ruins on your own this afternoon. Dinner together. Distance: 42 - 58 km (26 - 36 miles).

Day 6: Rest day in Volterra with optional bicycle ride

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Highlights: Etruscan archaeological site, Volterra, optional loop ride
This is a day for cycling into the hills surrounding Volterra, land of the ancient Etruscans, or a relaxing day strolling through town with a visit to the Etruscan archaeological site and museum. Those wanting to bicycle can leave early to make it back to Volterra for lunch, or can take it easy in the morning and enjoy lunch in one of the small hilltop towns. We'll offer a shuttle late morning for those wanting to avoid the climb back into Volterra! Dinner on your own. Today's optional mileage: 52-68 km (32-43 miles).

Day 7: Bicycle from Volterra to Siena

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Highlights: Cycle through Central Tuscan landscapes and rolling terrain, farewell dinner in historic Siena
Our bike ride today takes us through the picturesque clay hills of southwest Tuscany. Here, lonely shepherds guard their flocks and the occasional cypress tree punctuates the horizon. As we near Siena, olive trees and vineyards carpet the hills. Spend the rest of the day exploring Siena. This fascinating medieval city once rivaled Florence for supremacy in central Italy, and today retains its old-world charm. We'll enjoy a great farewell dinner together this evening. Today's ride: 70 km (44 miles).

Day 8: Our bicycle tour ends in Siena

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Highlights:
You are on your own after breakfast this morning. It is only a quick train ride from Siena to Florence, where you can catch trains going all directions. Our tour library is available to you for post-tour planning. Perhaps you'll go north to Venice, or south to Rome? Whatever your choice, have a great trip and thanks for cycling with ExperiencePlus!