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Self-Guided Tuscany Fast Bike Tour

Self-Guided 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.
Day 1 Radda  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 winery. Try their award winning wines at a guided tasting. 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 a hill town right out of a fairy tale.

Day 4-5 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 (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$ 1,000 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$ 100 (per person) will apply if you stay in Siena 6/29, 6/30, 7/1, 7/2, 8/13, 8/14, 8/15, or 8/16.

Save US$ 100 per person
Use our bike bags (panniers) instead of the luggage transfer
more info


Any date from March 1 to October 31
5 Days, 4 Nights
Route Rating
Moderate to Challenging: 20 to 40 miles (30-65 km) per day over hilly terrain.

Meet / Finish
Florence / Volterra
  • Winery and olive oil mill tour with guided wine and oil tasting
  • Optional castle and winery visit with wine tasting
  • Towns of Siena, San Gimignano, Volterra, 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
  • 4 beautiful rides. Extra miles available.
  • Use of high-end hybrid bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles

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.