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Self-Guided
Siena Bike Tour
When people think of cycling in Italy they think of Tuscany. Rolling hills, lush vineyards, and medieval villages make for a landscape right out of a Renaissance painting. Tuscany is home to the extraordinary Chianti Classico wine and this bike tour takes you through the heart of Chianti. You spend a night in Greve where you can enjoy a hand’s on cooking class. You tour a 400 year old winery and are treated to a guided wine tasting. In Radda you sojourn in a four-star hotel located in a renovated Renaissance Palace. Your tour ends in gothic Siena known for its beautiful architecture and annual bareback horse race known as the Palio. The tour features beautiful cycling on Tuscany’s prettiest back roads.
​Highlights
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Winery and olive mill visit with guided wine and oil tasting
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Abbey visit with winery and Renaissance gardens
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Towns of Greve, Radda, and Siena
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Beautiful Tuscan scenery and peaceful country roads
Price
US$ 1,000 per person, double occupancy
Dates
Any date, Mar 1 to Dec 1
Single Supplement
+ US$ 200 for single room occupancy
Length
5 Days, 4 Nights
Meet / Finish
Florence / Siena
Route Rating
Moderate: 15-19 miles (24-30 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
Day 4 and 5: Siena
Leaving Radda you head south to Siena, a perfectly preserved medieval town. The ride takes you off the beaten track past castles, sleepy villages, and an outdoor sculpture garden. 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. Frequent trains and busses make for an easy departure at tour's end.
Day 1: Greve
Meet your tour coordinator in Florence and shuttle to our bicycle storage in the Chianti countryside. A short 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. During lunch your tour coordinator passes out route notes and answers any questions. After lunch a panoramic downhill leads to the village of Greve. Your hotel is right on the central piazza of town. Before dinner you can explore a walled medieval village called Montefioralle or just find a nice spot in an outdoor cafe for a relaxing aperitif. An optional cooking class is available on Day 2.
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Day 2 and 3: Radda In Chianti
Cycle deeper into Chianti as you ride to Radda. Along the way you stop and visit the hill town of Panzano. 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. Pedal to a family-run ceramics shop where you can see the painting and firing of Italian majolica pottery. Tour the Renaissance gardens and cavernous wine cellars of an ancient abbey.
Daily Itinerary
Daily Distance
Lodging
Albergo del Chianti
Greve in Chianti (1 night)
Located in an 11th Century building on the main piazza of Greve, this family-run hotel has 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 (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 >
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All lodging (three and four star hotels)
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All breakfasts
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Lunch with your guide on Day 1
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Winery and olive mill visit with tastings
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Luggage transfers from hotel to hotel
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Private van transfer from Florence on Day 1
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4 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
What's Included
Departure from Siena, End of Tour
The bike tour ends in Siena. Siena is well connected to Florence and Rome by trains and busses. We will be happy to assist you with your post-tour travel plans.
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.
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.