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Florence to Siena Bike Tour

This two-day Tuscany bike tour takes you through the picture-perfect Chianti countryside as you slowly pedal from Florence to Siena. Cypress lined lanes and medieval villages create a scene right out of a Renaissance painting. You spend one night in Greve, the unofficial capital of Chianti, and one night in scenic Siena. You visit a 16th Century villa, tour their winery, and sample their wines and oils. Explore the bustling streets and piazzas of Siena as you search for the perfect gelato. Cycling in Italy can be hilly and this tour is no exception. However, the distances are not long and the views are spectacular. 


  • Winery and olive oil mill tour with tastings

  • The towns of Greve, Castellina, and Siena

  • 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 / Siena

Route Rating
Moderate: Two rides, 15 and 27 miles (27 and 43 km) over hilly terrain. Extra miles available.

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Terms and Conditions >

Daily Itinerary

Daily Itinerary

Day 1:  Greve
We meet in the center of Florence and shuttle to our bicycle storage in the Chianti countryside (9 miles south of Florence). This 20-minute drive gets you past the traffic of the city. Together we cycle to a Chianti Classico winery for a private tour of their wine cellars and olive mill. Lunch at the winery includes a wine and oil tasting. After lunch the self-guided part of your bike tour begins. A panoramic downhill leads you to the village of Greve. Your hotel is right on the central piazza of town. Before dinner you can explore Montefioralle, a fortified medieval hamlet, or just find a nice spot in an outdoor cafe for a relaxing aperitif.

Day 2 and 3:  Siena
You pedal the picturesque Chiantigiana road as it winds through the heart of Tuscany. Along the way you visit two Chianti villages. The town of Panzano was originally a medieval castle and still preserves some of its old walls and towers. A few miles down the road the town of Castellina offers a wealth of archaeological treasures including a 15th Century castle and Etruscan tombs from 700 BC. Climb the castle towers for 360 degree views. Inside the castle you will find a small archeological museum with bronze weapons, ornaments and Corinthian vases. Your cycling holiday ends in the traffic-free center of Siena. Today Siena offers Italy's best Gothic city experience. Frequent trains and busses make for an easy departure on day three.

Daily Distance

Daily Distance

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.



Albergo del Chianti
Greve in Chianti (1 night)

Located in an 11th Century building on the main piazza of Greve, this family-run hotel has a salt-water pool, air- conditioning, and a restaurant.

hotel website >

Hotel Athena
Siena (1 night)

A modern four-star hotel with all of the comforts. The Athena is located in the historic center and offers a beautiful terrace with views of Siena.

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 Siena, End of Tour

The bike tour ends in Siena. Siena is well connected to Florence and Rome by trains and busses. 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.

Siena Hotel Supplement During Palio

During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.

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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