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

Self-Guided Tuscany Bike Challenge Bike Tour

Self-Guided Tuscany Challenge Bike Tor
Want to climb 3,000 feet (900 meters) per day on a bike tour in Tuscany? Are you looking for multiple breathtaking vistas followed by fast and twisty descents? The best word to describe this cycling holiday is challenging. It was created specifically for the experienced cyclist. If you are a casual cyclist this trip is not for you. This bike tour rolls through the lush vineyards of Chianti Classico before turning toward the Tuscan coast and the Mediterranean Sea. The spectacular biking takes you past ancient castles, wineries, and stone farmhouses. Along the way you visit some of the most beautiful hill towns in Tuscany including Siena, San Gimignano, and Volterra. From vineyards to beaches you can see a lot of Tuscany in just six days.
Day 1 Siena  Meet your tour coordinator in the center of Florence and drive to our bicycle storage in the Chianti countryside. This morning you can participate in a winery tour, or if you prefer, depart immediately for Siena. The scenery today is quintessential Tuscan as you roll through vineyards and olive groves. The medieval villages of Greve, Panzano, and Castellina make for delightful rest stops. Overnight in Siena, a magical medieval town.

Day 2 Volterra  A scenic ride takes you through the Monteriggioni castle on your way to San Gimignano, a perfectly preserved 13th century village. Savior an artisan gelato while admiring San Gimignano's 14 stone towers. Cross a sun-drenched valley and climb to exquisite Volterra. Off the beaten tourist trail, Volterra has a Roman amphitheater and an Etruscan gate. Your hotel is located in the historic center just steps from the town's bustling piazzas.

Day 3 Massa Marittima  Ride through the "Valley of the Devil", so called because of its many geysers. Today this area produces ten percent of the world's geothermal energy. Picnic in Pomerance, a medieval hill town. Climb to 2,900 feet (900 mt) before a long descent through oak and chestnut forests. Spend the night in Massa Marittima, a walled town on a panoramic hill with views of the Mediterranean Sea.

Day 4 Castagneto Carducci  Pedal along the Etruscan Coast, aptly named for the people who populated this area over two millennia ago. Roll through Campiglia Marittima, Suvereto and Sasseta, medieval boroughs ensconced behind ancient stone walls. A quiet back road leads to your hotel in Castagneto Carducci, an enchanting village overlooking the sea. For extra distance, ride 5 miles (8 km) to the beach for a refreshing swim.

Day 5-6 Cecina  Follow the spectacular "Strada del Vino" (Wine Road) as it parallels the Tuscan coast. Some of Italy's most famous wines come from this area including Sassicaia, Ornellaia, and Guado al Tasso. Explore the beautiful Bolgheri castle and tour their winery learning about the Bordeaux grape varieties that thrive in their soil and micro climate. Cycle through the sleepy medieval villages of Casale Marittimo, Gaurdistallo, and Montescudaio. Tour ends in Cecina. Frequent trains make for an easy departure at the end of your cycling adventure in Italy.

Reserve This Tour Detailed Itinerary

US$ 1,550 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.


Any date from March 1 to October 31
6 Days, 5 Nights
Route Rating
Challenging: 26 to 54 miles (42-87 km) per day over very hilly terrain.

Meet / Finish
Florence / Cecina
  • Tuscan hill towns and coastal villages
  • Rolling hills of Chianti
  • Peaceful country back roads
  • Optional visit to Tuscan beach
  • Winery tour with wine tasting
  • 13th century castle

What's Included
  • All lodging (3 and 4 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 one
  • 5 beautiful rides. Extra miles available.
  • Use of high-end hybrid bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Difficulty Warning
This is very challenging tour with big hills. To do this tour you should be a very experienced cyclist capable of riding 54 mi with 4,403 ft of climbing in one day (87 km and 1,342 mt).

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. You can call in the morning 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.