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Self-Guided San Gimignano Bike Tour

Self-Guided San Gimignano Bike Tour
This cycling holiday highlights the splendors of central Tuscany. On this tour you stay in three of Tuscany's most beautiful hill towns, Certaldo, San Gimignano, and Volterra. Visit a country villa, tour their winery, and sample their full-bodied Chianti Classico wines. Stay in a 15th Century palace in the fortified hamlet of Certaldo. Cycle to San Gimignano and be enchanted by the town's 14 stone towers. You spend two nights in San Gimignano leaving plenty of time to explore. You can visit an abandoned castle or cycle to a medieval town famous for its crystal glassware production. Pedal through olive groves and vineyards to Volterra, an Etruscan fortress surrounded by lush countryside. Volterra hasn't been transformed by tourism and is perhaps Tuscany's best kept secret. The town proudly features a Roman amphitheater and the world's best Etruscan museum.

Day 1 Certaldo  We meet in the center of Florence and shuttle by van to our bike storage in the Chianti countryside. You ride to a 16th Century winery and enjoy a private guided tour. Day one includes a wine and oil tasting over lunch. After lunch pedal to the perfectly preserved medieval village of Certaldo. Your 4-star hotel features a pool and huge garden.

Day 2-3 San Gimignano  Cycle past a castle and vineyards on your way to San Gimignano. Along the way enjoy beautiful views of San Gimignano's stone towers. After lunch climb a tower, shop, or just savor a cappuccino in a pretty piazza. On day three you have the option of hiking to an abandoned castle, pedaling to a winery, or cycling to Colle di Val d'Elsa, famous for its crystal glassware. While in San Gimignano be sure to try the local Vernaccia wine, a tangy, crisp Tuscan white. If gelato is more your speed you can't go wrong at the Gelateria Di Piazza, described by many as one of the best gelaterias in Tuscany. Optional cooking class

Day 4-5 Volterra  We have saved the best cycling for last. Dense woodlands give way to peaceful rolling hills as the countryside opens up before you. Volterra is one of Tuscany's most beautiful hill towns, and yet remains well off the beaten tourist trail. Your hotel is in the historic center close to all the sites. Explore Volterra's Roman theater and marvel at its Etruscan gate. Frequent busses make for an easy departure from Volterra on day five.

Reserve This Tour Detailed Itinerary

US$ 1,000 per person
(Single Supplement)

Traveling alone?
Join a self-guided tour that has already been scheduled. We can't run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info

Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.

Save US$ 100 per person
Use our bike bags (panniers) instead of the luggage transfer
more info

Optional Charges
Cooking Class (US$ 150 per person)


Any date from March 1 to October 31
5 Days, 4 Nights
Route Rating
Moderate: 10-20 miles (15-30 km) per day cycling over hilly terrain.

Meet / Finish
Florence / Volterra
  • Winery and olive mill tour with tastings
  • Stone towers of San Gimignano
  • Roman theater of Volterra
  • Beautiful Tuscan scenery and peaceful country roads
  • The town of Volterra

What's Included
  • All lodging (3-star hotels)
  • All breakfasts
  • One lunch
  • Winery visit and wine tasting
  • Luggage transfers from hotel to hotel
  • Private van transfer from Florence on day one
  • 4 beautiful rides. Extra miles available.
  • Use of a high-end bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Optional cooking class?
Add a cooking class for US$ 150 (per person)
Chianti cooking class
Spend half a day with an Italian family at their country house. Learn to make traditional Tuscan cuisine with produce from the family garden. (vegetarian classes available).

What if it rains?

On self-guided bike tours there is no van support. However, we do move your luggage from hotel to hotel. In the event of rain you can catch a ride with us when we move your bags, just call and make arrangements for a lift.

Why a Self-Guided Bike Tour?
Explore Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates. We take care of the details.