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Tuscany Fast Bike Tour

Want a cycling holiday in Italy with longer rides? We have taken our seven-night Tuscany Bike Tour and compressed it into four nights giving you longer rides each day. This bike tour takes you on a loop through Tuscany's most famous hill towns. You cycle from Renaissance Florence to Medieval Siena and finish in Etruscan Volterra. Visit a castle, two wineries, and an olive oil mill. Indulge yourself in Tuscan specialties including sheep cheese, extra virgin olive oil, and bread soup. Enjoy personal encounters with Italians as you explore Tuscany at your own pace.


  • Winery and olive oil mill tour with guided tastings

  • Optional castle and winery visit with wine tasting

  • Towns of Siena, San Gimignano, Volterra, Greve,and Radda

  • Beautiful Tuscan scenery and peaceful country roads

US$ 1,000 per person, double occupancy

Any date, Mar 1 to Dec 1

Single Supplement
+ US$ 250 for single room occupancy

5 Days, 4 Nights

Meet / Finish
Florence / Cecina

Route Rating
Moderate: 19-33 miles (31-54 km) per day over hilly terrain. Extra miles available.

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Daily Itinerary

Daily Itinerary

Day 1:  Radda in Chianti

Meet your tour coordinator in the center of Florence and drive to our bicycle storage in the Chianti countryside. Cycle to a 16th Century villa where they make a ruby red Chianti Classico. Tour the winery and olive mill. Enjoy a guided wine tasting followed by lunch at the winery. Later a rolling ride through Chianti leads you to the village of Radda.

Day 2:  Siena

On your way to Siena stop at the Ricasoli castle and winery. It was here in 1872 that Bettino Ricasoli penned the formula for Chianti Classico. Tour the family's castle and their sprawling estate. Try their award winning wines. The road to Siena takes you off the beaten path through sleepy villages. Siena is best known for its bareback horse race known as the Palio. Your hotel is in the historic center within easy walking distance of the main sights.

Day 3:  San Gimignano

Stop for lunch in Monteriggioni, a 13th Sienese fortress. This small fortified town retains its original medieval walls and stone watch towers. Your destination is San Gimignano a quintessential Tuscan hill town. Imagine a medieval stone village, high on a hill, surrounded by a manicured landscape of grape vines and olives trees. Add a wall and stone towers and you have San Gimignano.

Day 4 and 5:  Volterra

One of the most beautiful rides in Tuscany awaits you as you leave San Gimignano. Volterra sits on a sandstone ridge dominating a vast, unspoiled countryside. Cultivations of cereals and sunflowers change color with the seasons. Volterra was founded by the Etruscans and later conquered by the Romans. Today you can visit a Roman amphitheater or an Etruscan gate. Frequent busses depart daily from Volterra. A taxi can be arranged for transport to a train station 30 minutes away.

Daily Distance

Daily Distance


Hotel San Niccolo'
Radda in Chianti (1 night)

This four-star hotel is located in a 15th Century palace. The rooms feature wooden ceiling beams, terracotta floors, and marble bathrooms.

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 >

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 >

Hotel La Locanda
Volterra (1 night)

This four-star hotel is located in a converted nunnery in the historic center of Volterra. The hotel has air-conditioning, free WIFI, and a small garden.

hotel website >

What's Included

  • All lodging (three and four star hotels)

  • All breakfasts

  • One lunch

  • Winery visit and wine tasting

  • Luggage transfer from hotel to hotel

  • Private van transfer from Florence on Day 1

  • Four 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

What's Included

Departure from Volterra, End of Tour

The bike tour ends in Volterra. Volterra does not have a train station or rental car agencies. However, Volterra is well connected by busses. The busses to Florence or Pisa take 2 hours. If you prefer we can book a taxi for you. We will be happy to assist you with your post tour travel plans.

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.

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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