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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.


  • 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

US$ 600 per person, double occupancy

Any date, Mar 1 to Dec 1

Single Supplement
+ US$ 100 for single room occupancy

3 Days, 2 Nights

Meet / Finish
Florence / San Gimignano

Route Rating
Moderate: Two rides, 19 and 9 miles (31 and 14 km) over hilly terrain. Extra miles available.

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Daily Itinerary

Daily Itinerary

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 and 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.

Daily Distance

Daily Distance



Hotel Certaldo
Certaldo (1 night)

The four-star Hotel Certaldo is located in a renovated watermill on the Elsa river. The hotel has air-conditioning, a pool, a great breakfast, and super friendly staff. 

hotel website >

Hotel Leon Bianco
San Gimignano (1 night)

You stay in an 11th Century palace on San Gimignano's most beautiful piazza. The building has been carefully restored preserving its special character.

hotel website >

What's Included

What's Included

  • ​All lodging (three and four star hotels)

  • All breakfasts

  • Lunch with your guide on Day 1

  • Winery and olive mill visit with tastings

  • Luggage transfers from hotel to hotel

  • Private van transfer from Florence on Day 1

  • 2 beautiful rides (extra miles available)

  • Use of a high-end bicycle (hybrid, road bike or e-bike)

  • Use of a helmet

  • Souvenir water bottle to keep

Departure from San Gimignano, End of Tour

The bike tour ends in San Gimignano. The town does not have a train station but is well connected by busses. There are no car rental agencies in San Gimignano, although taxis are available.  We will be happy to assist you with your post tour travel plans.

Use our Bike Bags (Panniers) and Save

Save US$ 50 per person.  Pack what you need in our bike bags (panniers) and leave the rest of your luggage with us. We will deliver your remaining luggage to the last hotel.

Can I really start any date I want?

Yes! You can start your tour any day of the week, March 1 through December 1. We have complete flexibility with the starting dates.

What If It Rains?

On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.

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