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Guided San Gimignano Bike Tour

Guided San Gimignano Bike Tour
Cycling in Tuscany is the best way to experience the region’s postcard-perfect landscapes. On our Guided San Gimignano Bike Tour you roll past ancient hilltop fortresses, vine-planted hillsides, and sculptural stands of cypress trees. You sojourn in the miraculously preserved medieval hill towns of Certaldo, San Gimignano, and Volterra. On this cycling adventure you explore a Renaissance garden, tour an ancient winery, and prepare a delectable lunch during a hands-on cooking class. With five days to relax you can thoroughly immerse yourself in the culture and beauty of Tuscany. Van support is available every day for tired riders or spur of the moment purchases.
Day 1 Certaldo  Meet in Florence and shuttle by van to our bike storage in the Chianti countryside. Ride to a 16th Century winery for a tour and wine tasting. Lunch together at the winery. After lunch pedal to the perfectly preserved medieval village of Certaldo. Our hotel is housed in a 16th Century four mill and features a swimming pool and a wellness center that offers massages and spa therapies.

Day 2-3 San Gimignano  Cycle past a castle and vineyards on your way to San Gimignano. Enjoy spectacular views of San Gimignano's fourteen stone towers. After lunch climb a tower or just savor a cappuccino in a bustling piazza. Ride to a small inn for a hands-on cooking class where you combine fresh locally sourced ingredients to create tasty Tuscan specialties.

Day 4-5 Volterra  We have saved the best riding for last. Lush woodland gives way to peaceful rolling hills as the countryside opens up before you. Volterra is one of Tuscany’s most beautiful hill towns and remains delightfully off the tourist trail. Volterra is known for its alabaster. You can visit a workshop where skilled artisans work the translucent stone into colorful creations. Volterra also has a well preserved Roman theater and Etruscan gate.

Reserve This Tour Detailed Itinerary

US$ 1,250 per person
($200 Single Supplement)

Tour prices are based on double room occupancy. A single supplement is required for single room occupancy. Please note that in Italy single rooms are frequently smaller than double rooms. Groups of three can book triple rooms and avoid the single supplement.

2018 Dates

September 10-14
September 28-October 2
October 20-24

5 Days, 4 Nights
Route Rating
Moderate: 10-20 miles (15-30 km) per day cycling over hilly terrain.

Meet / Finish
Florence / Volterra
  • Hands-on cooking class
  • Winery visit with guided wine and oil tasting
  • Towns of Certaldo, San Gimignano, and Volterra
  • Beautiful Tuscan cycling (peaceful roads and van support)

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • Two lunches
  • Cooking class with lunch
  • Winery visit and wine tasting
  • Private van transfer from Florence on day 1
  • 4 beautiful rides. Extra miles available.
  • Use of high-end hybrid bicycle
  • Van support
  • Friendly bilingual guide

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Dates don't work?
Consider one of our self-guided bike trips. We can schedule a self-guided bike tour whenever you want March 1 to October 31.

Have a group of four or more?
With a group of four or more we can schedule a guided bike tour when you want.