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Guided
Siena Bike Tour
A Tuscany bike tour is perfect for foodies and cyclists alike. Our Guided Siena Bike Tour features culinary delights and breathtaking rides. You cycle from Renaissance Florence to Medieval Siena. You pedal through Chianti, Italy's most famous wine making region. While known for its wines, Chianti also produces smooth flavorful olive oils as well as fresh cheeses. You visit a 16th Century villa, tour their winery, and sample their full-bodied wines. You learn about Tuscan cuisine during a hands-on cooking class. You visit the Castello di Brolio, a fairy tale castle with endless views. On this guided tour you will see the hilltowns and the landscapes, but you will also meet Italians as you learn more about their culture and cuisine.
​Highlights
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Hands-on cooking class
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Winery and olive mill tour with guided wine and oil tasting
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Castle visit
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Towns of Greve, Radda, and Siena
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Beautiful Tuscan cycling (peaceful roads and van support)
Price
US$ 1,400 per person, double occupancy
Dates
May 26-30, 2025
Email us your dates. We can schedule the tour when you want.
Single Supplement
+ US$ 200 for single room occupancy
Length
5 Days, 4 Nights
Meet / Finish
Florence / Siena
Route Rating
Moderate: 13-19 miles (21-30 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
Daily Itinerary
Day 1: Greve
Meet your guide 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 enjoy a guided wine tasting and lunch. After lunch a panoramic downhill leads you to the village of Greve. Your hotel is right on the central piazza.
Day 2: Radda in Chianti
Today you experience hill towns in Tuscany. In the morning a slow steady climb leads to Panzano. Enjoy a drink in the main piazza before a breathtaking descent through vinyards. For extra miles cycle to Volpaia, a marvelous medieval hamlet high on a hill. Your ride ends in Radda, a fortified village surrounded by wineries. Your four-star hotel is in the historic center. Tonight you have a hands-on cooking class in a Renaissance palace. Using fresh local ingredients an Italian chef will guide you through the preparation of a 3-course feast.
Day 3: Radda in Chianti
You follow the Eroica route on your way to the beautiful Brolio castle. From the back of the castle, you will find sweeping views all the way to Siena. For lunch we ride to the Abbey of the Good Harvest (La Badia a Coltibuono). This 11th Century abbey is now privately owned. Enjoy a meal at their spectacular restaurant (not included in tour price) and tour their gardens and wine cellars.
Day 4 and 5: Siena
Leaving Radda you bike south through a classic Tuscan landscape of gentle rolling hills, vineyards, and olive groves. Stop at a family-run ceramics shop and see how handpainting transforms simple pottery into colorful pieces of art. You ride ends in Siena, a city with a gorgeous gothic center. Siena is known for its alluring architecture, bustling piazzas, and annual bareback horse race called the Palio. Your hotel is in the historic center and within easy walking distance of Siena's main sights.
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 Palazzo Ravizza
Siena (1 night)
A historic hotel in the heart of Siena, the 19th Century Palazzo Ravizza has elegant rooms with antique furniture and modern amenities.
hotel website >
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, winery on DAY 1
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One dinner, cooking class
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Winery visit and wine tasting
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Abbey visit (winery and gardens)
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Castle visit
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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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Van support
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Friendly bilingual guide
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Use of a high-end bicycle (hybrid or road bike)
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Use of a helmet
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Souvenir water bottle to keep
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.
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.
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.
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.
Want to Save?
Consider one of our self-guided bike trips. We can schedule a self-guided bike tour whenever you want March 1 to October 31.
Our Dates Dont Work?
We may be able to offer the dates you want. Email us with the dates you prefer.