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Highlights: Bike fittings and introductory dinner in Greve in Chianti

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 the 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

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.

Distance: 70 km[footnoteRef:1] [1: Day 3 is the longest day of the tour.]

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

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

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.

Distance: 52-68 km

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.

Distance: 70 km

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 enjoy cycling in Italy!

Kilometers to Miles Conversion

1 km = 0.62 miles

40 km = 24.8 miles

60 km = 37.2 miles

80 km = 49.6 miles

Italy Tour