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Self-Guided Siena Bike Tour

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.
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.

Day 2-3 Radda  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.

Day 4-5 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.

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

Optional Charges
5th night (US$ 200 per person)
Cooking Class (US$ 150 per person)


Any date from March 1 to October 31
5 Days, 4 Nights
Route Rating
Moderate: 10-20 miles (15-30 km) per day cycling over hilly terrain.

Meet / Finish
Florence / Siena
  • Winery visit with guided wine and oil tasting
  • Abbey visit with winery and Renaissance gardens
  • Towns of Greve, Radda, and Siena
  • Beautiful Tuscan scenery and peaceful country roads

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • One lunch
  • Winery and olive mill visit with tastings
  • Luggage transfers from hotel to hotel
  • Private van transfer from Florence on day one
  • 4 beautiful rides. Extra miles available.
  • Use of a high-end bicycle

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Want an easier tour?
Add a fifth night for US$ 200 (per person)

Make your trip one day longer with EASIER cycling and stay in beautiful Castellina.

Optional cooking class?
Add a cooking class for US$ 150 (per person)
Chianti cooking class
Spend half a day with an Italian chef. Create a three course meal using fresh local ingredients (vegetarian classes available).

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.