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Self-Guided Florence to San Gimignano Bike Tour

Self-Guided Florence to San Gimignano Bike Tour
From the Renaissance splendors of Florence to the medieval stone towers of San Gimignano, this two-day cycling holiday in Italy shows you the wonders of central Tuscany. You tour a winery that makes the bold Chianti Classico, sampling their wines and flavorful olive oils. You spend the night in the ancient village of Certaldo, a red-brick medieval masterpiece. Certaldo is off the beaten trail and features beautiful views of the countryside as well as a 14th Century castle. On day two you cycle through vineyards and olive groves on your way to scenic San Gimignano. With its 14 stone towers San Gimignano looks like it was plucked from a fairy tale. There is a lot to see while cycling in Tuscany so we kept rides short leaving you plenty of time to explore.
Day 1 Certaldo  We meet in the center of Florence and shuttle to our bicycle storage in the Chianti countryside. This short drive gets you past the traffic of Florence. We fit you on your bike and you are off to a Chianti Classico winery. We tour the wine cellars seeing barrels and bottles. You learn about the local Sangiovese grapes and extra virgin olive oils. The tour culminates with a guided tasting and lunch. After lunch the self-guided part of your bike tour begins. You cycle through a picture-perfect landscape on your way to the village of Certaldo. Your four-star hotel has an inviting pool and gardens. Walking the stone streets of Certaldo Alto you will be able to see the towers of San Gimignano in the distance. Tour the castle or enjoy a cold drink in a peaceful piazza.

Day 2-3 San Gimignano  After a buffet breakfast you leave your bags in the lobby and roll into the Tuscan countryside. Two roads lead to San Gimignano giving you a choice. One ride heads steeply uphill as it meanders through picturesque villages. The other gently zigzags past vine covered slopes offering great views of San Gimignano's towers. As with many Tuscan hill towns, San Gimignano's medieval stone buildings have been perfectly preserved, but here 14 medieval towers are still standing as well. Declared by the United Nations to be a World Heritage site, the towers and palaces are a wonder to see. For dinner enjoy homemade pasta and sip Tuscany's best known white wine, the dry Vernaccia di San Gimignano. Frequent bus service makes for an easy departure on day three.

Reserve This Tour Detailed Itinerary

US$ 600 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$ 50 per person
Use our bike bags (panniers) instead of the luggage transfer
more info


Any date from March 1 to October 31
3 Days, 2 Nights
Route Rating
Moderate: Two rides, 19 and 9 miles (30 and 15 km) over hilly terrain.

Meet / Finish
Florence / San Gimignano
  • Winery visit with guided wine and oil tasting
  • The Tuscan hill towns of San Gimignano and Certaldo.
  • Beautiful vistas of vineyards and olive groves
  • Peaceful country back roads

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

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Want to see Volterra?
Add a third night for US$ 200 (per person)

Make your trip one day longer and stay in beautiful Volterra.

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.