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Tuscany Bike Tour

Our Self-Guided Tuscany bike tour takes you on a loop through the most famous hill towns of Tuscany. This is simply some of the prettiest cycling in Italy. You ride from Renaissance Florence to Gothic Siena and on to Medieval San Gimignano. Pedal along the old Chianti road known as the Chiantigiana. Visit a 16th Century villa, tour their winery, and sample their full-bodied reds. Take a guided tour of a 15th Century abbey, exploring their Renaissance gardens and wine cellars. Indulge yourself in Tuscan specialties including sheep cheese, extra virgin olive oil, and white truffle mushrooms. Discover back roads, towns, and sights that most visitors miss.


  • Winery and olive mill visit with guided wine and oil tasting

  • Abbey tour including their winery and Renaissance gardens

  • Two castle visits

  • Towns of Siena, San Gimignano Greve, and Radda

  • Beautiful Tuscan scenery and peaceful country roads

US$ 1,700 per person, double occupancy

Any date, Mar 1 to Dec 1

Single Supplement
+ US$ 400 for single room occupancy

8 Days, 7 Nights

Meet / Finish
Florence / San Gimignano

Route Rating
Moderate: 13-19 miles (21-31 km) per day over hilly terrain. Extra miles available.

Bikes and Gear >

Terms and Conditions >

Daily Itinerary

Daily Itinerary

Day 1:  Greve in Chianti

You meet your tour coordinator in the center of Florence and drive to our bicycle storage in the Chianti countryside. A short bike ride takes you to a 16th Century villa where they make a ruby red Chianti Classico. You tour the winery and sit down for a guided wine tasting and lunch. After lunch a panoramic downhill leads you to the village of Greve.

Day 2 and 3:  Radda in Chianti

Day two takes you deeper into Chianti on your way to Radda. The landscape is classic Tuscan with gently rolling hills covered with vineyards and olive groves. In Radda you stay in a four-star hotel in the historic center. The Renaissance palace that hosts the hotel has been remodeled to offer all of the modern comforts while retaining its beautiful character. On day three stop at a family-run ceramics shop on your way to the Abbey of the Good Harvest (La Badia a Coltibuono). This 11th Century monastery is now privately owned. Enjoy a meal at their spectacular restaurant and tour their gardens and wine cellars.

Day 4 and 5:  Siena

Leaving Radda you head south on your way to Siena, a well preserved Gothic town. Your ride takes you off the beaten track past a sculpture garden and sleepy villages. An optional ride leads to the Brolio castle and winery. You can tour the castle grounds and try their wine. Siena is best known for its bareback horse race known as the Palio (run twice per year). Your hotel is in the historic center and within easy walking distance of Siena's main sights. With two nights in Siena you have plenty of time to explore. 

Day 6:  Monteriggioni

Cycling the old Chianti road known as the Chiantigiana you pedal to the quintessential walled village of Monteriggioni. The overlords of Siena built this fortress in the early 13th Century. Except for some work in the 1700s, little has changed. Today Monteriggioni's walls and buildings are the best preserved example of their kind in all of Italy. Climb the walls for views of the countryside or head to a wine bar to try the local red.

Day 7 and 8:  San Gimignano

Imagine a fairytale village high on a hill surrounded by a manicured landscape of grape vines and olive trees. Now add a wall and 14 stone towers and you have San Gimignano, your destination on day seven. Climb a stone tower, try some pasta with a wild boar sauce, or just shop. Your hotel in the center of town allows easy access to all of the main attractions. Frequent bus service makes for an easy departure at the end of your tour.

Daily Distance

Daily Distance


Albergo del Chianti
Greve in Chianti (1 night)

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

hotel website >

Hotel San Niccolo'
Radda in Chianti (2 nights)

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 (2 nights)

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 Il Piccolo Castello
Monteriggioni (1 night)

Il Piccolo Castello is located within the ancient walls of Monteriggioni. The rooms feature renovated bathrooms and views of the surrounding countryside.

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 on Day 1

  • Winery visit and wine tasting

  • Luggage transfer from hotel to hotel

  • Private van transfer from Florence on Day 1

  • Six 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.

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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