Heart of Tuscany: Special Edition
Palio di Siena
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On this special edition of our traditional Tuscan tour, you are part of an event that you will never forget: the Palio di Siena. From the quaint town of Radda in Chianti to Bagno Vignoni, we cycle through the Tuscan countryside along Via Chiantigiana (literally, Chianti Street). This classic and rustic route passes through the heart of the Chianti wine region. The landscape resembles a Renaissance painting alive with wildflowers in the spring and crushed grapes in the fall. Along our way, we stop in Siena, where a medieval air lingers amidst the twisting streets of warm, brown brick. We participate in one of Italy’s most popular traditions: the Palio! The horse race that takes place in the main square represents the most important event happening in town. Our group will experience the atmosphere of a “Contrada” at the inaugural dinner on the previous night and see the race from a privileged point of view. On the final two days of the tour, the route leads to the Val d’Orcia, a UNESCO World Heritage site characterized by the smooth shape of the hills, the tiny stone village, and the unique Montalcino vineyards.
Tour Essence
- Stay in luxury hotels and countryside inns
- Learn more about Tuscan cuisine, wines, and olive oil in exclusive visits to the home of local producers
- Enjoy memorable rides in the Chianti area
- Enjoy a “Contrada” dinner
- Watch the Palio from an exclusive balcony in Piazza del Campo
- Ride through the Crete Senesi on one of the most beautiful bike rides in Tuscany
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Immerse yourself in Tuscan lifestyle with a cooking class
- Ride to Montalcino, home of the most famous Tuscan red wine: the Brunello di Montalcino
What to Expect
Terrain
Rolling and hilly with breathtaking viewsStart Location
Radda in ChiantiEnd Location
Bagno VignoniMileage
Average Daily: 29/36 miles Total: 174/220 milesElevation
Average Daily: 2,710/3,347 ft Total: 16,263/20,085 ft
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Van support
- Service of local, professional guides throughout the program
- Ciclismo jersey and water bottle
- Cooking class by local chef
- Olive oil tasting
- 2 wine tastings
- Guided walking tour of Siena
- Cycling clinics
- Shuttle at the beginning and end of the tour
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: Map holder on handlebar
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 3 lunches + 1 picnic
- 5 dinners
Chianti is a wine practically synonymous with Italy, benefiting from an unparalleled terroir that nurtures the best in Italian reds—something you quickly appreciate on our Tuscany cycling adventures. We pedal first to Montalcino, the hometown of the most famous Tuscan red, the Brunello di Montalcino. We also track through Greve and Panzano, immersing ourselves in Chianti along the way!
Complemented by outstanding meals, you also learn from the experts about the finer points of Tuscan cuisine and its excellent olive oils. Visiting the homes of renowned local producers (some of whom are your Ciclismo Classico guides), you take part in cooking class in authentic Tuscan cuisine. We also visit the UNESCO World Heritage Site of Val d’Orcia and ride the “Crete Senesi,” one of the most beautiful Tuscany bike routes.
2025
Start Location
Radda in ChiantiFly Into
Florence or RomeEnd Location
Bagno VignoniFly Out Of
Florence or RomeRadda warm-up ride
Meals Provided
Lunch, DinnerAverage Mileage
14 / 20 milesElevation Gain
1,144 / 1,888 ftRiding Terrain
Rolling with a few hillsMeals Provided
Lunch, DinnerAccommodations
Palazzo Leopoldo
A noble palace overlooking the vineyards of Chianti, in the heart of Radda that relives the charm and fascination of Tuscany of yore: today Palazzo Leopoldo is an elegant 4-star hotel, where antique furnishings coexist with contemporary amenities. The hotel has a captivating spa and wellness corner, a typical Tuscan restaurant, and a private wine bar.
The Chianti
Meals Provided
Breakfast, DinnerAverage Mileage
30 / 44 milesElevation Gain
3,723 / 5,261 ftRiding Terrain
Rolling hills with one long climbMeals Provided
Breakfast, DinnerAccommodations
Palazzo Leopoldo
A noble palace overlooking the vineyards of Chianti, in the heart of Radda that relives the charm and fascination of Tuscany of yore: today Palazzo Leopoldo is an elegant 4-star hotel, where antique furnishings coexist with contemporary amenities. The hotel has a captivating spa and wellness corner, a typical Tuscan restaurant, and a private wine bar.
Siena
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
30 / 32 milesElevation Gain
2,134 / 2,445 ftRiding Terrain
Hilly, and a longer climb on the extra loopMeals Provided
Breakfast, Lunch, DinnerAccommodations
Hotel Palazzetto Rosso
Palazzetto Rosso Boutique Hotel is located in the heart of the medieval town of Siena. The red brick walls hotel has been hosting travelers since the Middle Ages when traders from all over the world came to Tuscany. A lot has changed since the hotel’s original days, but the original façade remains the same with its traditional wrought-iron ensigns and flares.
Siena & Monteriggioni Loop
Meals Provided
BreakfastAverage Mileage
Rest day / optional 24-mile rideElevation Gain
1,770 ftRiding Terrain
RollingMeals Provided
BreakfastAccommodations
Hotel Palazzetto Rosso
Palazzetto Rosso Boutique Hotel is located in the heart of the medieval town of Siena. The red brick walls hotel has been hosting travelers since the Middle Ages when traders from all over the world came to Tuscany. A lot has changed since the hotel’s original days, but the original façade remains the same with its traditional wrought-iron ensigns and flares.
Siena to Bagno Vignoni
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
43 / 55 milesElevation Gain
3,540 / 4,494 ftRiding Terrain
Undulating with some climbsMeals Provided
Breakfast, Lunch, DinnerAccommodations
Posta Marcucci
The family-run 4-star hotel Posta Marcucci is located in the pedestrian village and spa town of Bagno Vignoni. It has simple, elegant, and cozy rooms, a large outdoor thermal swimming pool, and indoor pools. The Spa offers hydro-massages, a Finnish and bio-saline sauna, and a Turkish bath.
Loop to Montalcino
Meals Provided
Breakfast, Picnic, DinnerAverage Mileage
33 / 45 milesElevation Gain
3,952 / 4,227 ftRiding Terrain
Lots of ups and downs with some long climbsMeals Provided
Breakfast, Picnic, DinnerAccommodations
Posta Marcucci
The family-run 4-star hotel Posta Marcucci is located in the pedestrian village and spa town of Bagno Vignoni. It has simple, elegant, and cozy rooms, a large outdoor thermal swimming pool, and indoor pools. The Spa offers hydro-massages, a Finnish and bio-saline sauna, and a Turkish bath.
