Heart of Tuscany: Special Edition
Tour de France and Palio di Siena
Download a Detailed Itinerary
Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:
- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
Please provide your contact information so that we can say “benvenuto”. After submitting the form, you will be able to download the itinerary immediately.
On this special edition of our traditional Tuscan tour, you are part of two events that you will never forget: the Tour de France and the Palio di Siena.
The adventure starts in Florence, where the 2024 Tour de France begins. From there, we reach the quaint town of Radda in Chianti and ride to the Val d’Orcia, crossing the Tuscan countryside along Via Chiantigiana (literally, Chianti road). 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. 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 Tuscany luxury hotels and countryside inns
- Participate in a Team Presentation and departure of the Tour de France
- Enjoy a “contrada” dinner
- Watch the Palio from an exclusive balcony in Piazza al campo
- Learn more about Tuscan cuisine, its wines and its olive oils, with exclusive visits to the homes of local producers
- Memorable Tuscany cycling routes through the Chianti area
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Ride through the Crete Senesi on one of the most beautiful bike rides in Tuscany
- Ride to Montalcino, home of the most famous Italian red wine: Brunello di Montalcino
What to Expect
Terrain
Rolling and hilly with breathtaking viewsStart Location
FlorenceEnd Location
MontalcinoMileage
Average Daily: 29/36 miles Total: 174/220 milesElevation
Average Daily: 2,710/3,347 ft Total: 16,263/20,085 ftOnce 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
- Exclusive access to a stand for the Palio
- Olive oil tasting
- 2 wine tastings
- Guided walking tour of Florence and Siena
- Cycling clinics
- Shuttle at the 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
- 6 dinners
Chianti is a wine practically synonymous with Italy itself, benefiting from an unparalleled terroir that nurtures the best in Italian reds—something you’ll quickly appreciate on our Tuscany cycling adventures. We’ll pedal first to Montalcino, hometown of the most famous Tuscan red, Brunello di Montalcino. We also track through Greve and Panzano, literally immersing ourselves in Chianti along the way!
Complemented by outstanding meals, you’ll also learn from the experts about the finer points of Tuscan cuisine, and its wonderful olive oils. Visiting the homes of renowned local producers (some of whom are your Ciclismo Classico guides), you’ll take part in cooking lessons in authentic Tuscan cuisine. We’ll also visit the UNESCO World Heritage Site of Val d’Orcia and ride the “Crete Senesi,” one of the most beautiful Tuscany bike routes.
2024
Start Location
FlorenceFly Into
FlorenceEnd Location
MontalcinoFly Out Of
Florence or RomeTour de France Presentation
Meals Provided
Lunch, DinnerMeals Provided
Lunch, DinnerAccommodations
Hotel Silla
The Hotel Silla distinguishes itself for its excellent comforts and services and a breathtaking rooftop terrace on the Arno. The friendly, family-run hotel within the historic Demidoff building offers an expert multilingual staff.
Florence to Chianti
Meals Provided
Breakfast, DinnerAverage Mileage
14 / 20 milesElevation Gain
1,144 / 1,888 ftRiding Terrain
Rolling with a few hillsMeals 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.
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
Optional 24 milesElevation 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, DinnerAverage Mileage
33 / 45 milesElevation Gain
3,952 / 4,227 ftRiding Terrain
Lots of ups and downs with some long climbsMeals Provided
Breakfast, 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.