Charnes Tours Logo
Toll Free:  1-888-491-2760

Self-Guided Tuscany Bike Tour

Self-Guided 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 Medieval Siena and San Gimignano. An extra night option is available in Etruscan Volterra. 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 off-the-beaten trail secrets that most visitors miss.
Day 1 Greve  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 2-3 Radda  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 4-5 Siena  Leaving Radda you head south on your way to Siena, a perfectly preserved Medieval town. Your ride takes you off the beaten track past castles and sleepy villages. 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 7-8 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. End your tour here or add an extra night in Volterra. Frequent bus service makes for an easy departure from San Gimignano.


Day 8-9 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 below. 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 (100 AD) or an Etruscan gate (400 BC). Frequent busses depart daily from Volterra. Private cars can be arranged for transport to a train station 30 minutes away.

Reserve This Tour Detailed Itinerary

US$ 1,700 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.

(Siena Palio Surcharge)

During the Palio (Siena's famous horse race) hotel prices
triple. A surcharge of US$ 200 (per person) will apply if you stay in Siena two nights from 6/29 to 7/2 or 8/13 to 8/16.

Save US$ 175 per person
Use our bike bags (panniers) instead of the luggage transfer
more info

Optional Charges
8th night (US$ 200 per person)


Any date from March 1 to October 31
8 Days, 7 Nights
Route Rating
Moderate: 10-20 miles (15-30 km) per day cycling over hilly terrain.

Meet / Finish
Florence / San Gimignano or Volterra
  • Winery visit with guided wine and oil tasting
  • Abbey visit with winery and Renaissance gardens
  • Towns of Siena, San Gimignano Greve, and Radda
  • Beautiful Tuscan scenery and peaceful country roads

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • One lunch
  • Winery visit and wine tasting
  • Luggage transfer from hotel to hotel
  • Private van transfer from Florence on day one
  • 6 beautiful rides. Extra miles available.
  • Use of high-end hybrid bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Want to see Volterra?
Add an eighth 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.