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Self-Guided
Tuscany Challenge Bike Tour
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.
​Highlights
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Winery and olive mill tour with wine and oil tastings
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Tuscan beach visit
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Chianti castle visit
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Rolling hills of Chianti
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Coastal scenery
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Beautiful hill towns
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Peaceful country back roads
Price
US$ 1,550 per person, double occupancy
Dates
Any date, Mar 1 to Dec 1
Single Supplement
+ US$ 250 for single room occupancy
Length
6 Days, 5 Nights
Meet / Finish
Florence / Volterra
Route Rating
Moderate: 26-51 miles (42-82 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
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.
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Day 5 and 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. Your Cecina hotel is just a 5-minute walk from the beach. Frequent trains make for an easy departure at the end of your cycling adventure in Italy.
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.
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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.
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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.
Daily Itinerary
Daily Distance
Lodging
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 La Locanda
Volterra (1 night)
This four-star hotel is located in a converted nunnery in the historic center of Volterra. The hotel features air-conditioning, free WIFI, and a small garden.
hotel website >
Fenice Park Hotel
Massa Marittima (1 night)
The Fenice Park Hotel is an elegant hotel in the center of Massa Marittima. The hotel offers large rooms, a swimming pool, air-conditioning, and WIFI.
hotel website >
Camere di Via Montebello
Castagneto Carducci (1 night)
This small guest house is located in a house from the 1700s. A high-end renovation was completed providing modern amenities while maintaining that old-world charm.
Hotel Golden Residence
Cecina (1 night)
This hotel is 500 meters from the Marina di Cecina Beach. All of the recently renovated, air-conditioned rooms, face the hotel pool.
What's Included
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All lodging (three and four star hotels)
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All breakfasts
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One lunch
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Winery visit and wine tasting
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Luggage transfer from hotel to hotel
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Private van transfer from Florence on Day 1
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Four beautiful rides (extra miles available)
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Use of a high-end bicycle (hybrid, road bike or e-bike)
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Use of a helmet
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Souvenir water bottle to keep
Departure from Cecina, End of Tour
The last hotel is 1.6 mi (2.6 km) from the Cecina train station. You can walk 30 minutes, or take a short taxi ride. Frequent trains make for easy departures. The train to Rome takes 3 hours while the train to Florence takes 2 hours.
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.
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.
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.
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.
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.
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.
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.