Tuscany and L’Eroica
A Southern Tuscan Spin paired with an Unforgettable Taste of Vintage cycling at its Best
Spend a week savoring Tuscan roads, food, and wine: from the quaint countryside of Serre di Rapolano to the Chianti area, via the Val d’Orcia and through medieval Siena, where an air lingers amidst the twisting streets of warm, brown brick.
This itinerary will be a special one: a combination of the classic Heart of Tuscany enriched by the rustic feeling of the Agriturismo Il Molinello and enhanced with some new spectacular rides. Day after day, pedaling among olive groves and wine yards, you’ll breath in the spirit of old-time cycling that will be celebrated with a grand finale. “L’Eroica, Gaiole” will thrill you as you’ll be part of the world’s most famous vintage cycling festival. People from all over the world will gather in Gaiole to ride the white gravel roads of Toscana and share an epic day of sport, friendship and fun.
Tour Essence
- Ride L’Eroica, the world’s greatest cycling event
- 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 (and Ciclismo guides!)
- Take memorable rides in the Chianti area
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Ride the “Crete Senesi,” one of the most beautiful rides in Tuscany
- Immerse yourself in Tuscan life with a cooking lesson
- View our Top Photos from Tuscany and L’Eroica
What to Expect
Terrain
Rolling and hilly with breathtaking viewsStart Location
Serre di RapolanoEnd Location
RaddaMileage
Average Daily: 30 miles Total: 207 milesOnce 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
- Expert, bilingual guides
- 2 wine tastings
- 1 Tuscan cooking lesson, 1 olive oil lesson, and 1 Italian lesson
- Guaranteed entrance to L’Eroica
- 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)
- Vintage bike rental for the Eroica
- Garmin Edge Touring 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, and 6 dinners
- Guided walking tour of Siena
- Olive oil tasting
- Cooking lesson by a local chef
- Multiple Eroica and Vintage bikes lectures and tutorials
Start Location
Serre di RapolanoFly Into
End Location
RaddaFly Out Of
Serre di Rapolano Warm-up Ride
Meals Provided
Lunch, DinnerAverage Mileage
13 milesElevation Gain
870 ftRiding Terrain
RollingMeals Provided
Lunch, DinnerAccommodations
Agriturismo Il Molinello
It’s back to nature at Agriturismo Il Molinello, a restructured farmhouse where Top Guide Sandro and his family reside. The picturesque location in the characteristic Tuscan landscape outside of Siena is full of soft hills and beautiful scenery.
Val D'Orcia Loop to Pienza
Meals Provided
Breakfast, DinnerAverage Mileage
38/50 milesElevation Gain
3300/4100 ftRiding Terrain
Rolling with 2 main climbsMeals Provided
Breakfast, DinnerAccommodations
Agriturismo Il Molinello
It’s back to nature at Agriturismo Il Molinello, a restructured farmhouse where Top Guide Sandro and his family reside. The picturesque location in the characteristic Tuscan landscape outside of Siena is full of soft hills and beautiful scenery.
Montalcino
Meals Provided
B,L,DAverage Mileage
35/53 milesElevation Gain
2700/4200 ftRiding Terrain
Rolling with short major climbsMeals Provided
B,L,DAccommodations
Agriturismo Il Molinello
It’s back to nature at Agriturismo Il Molinello, a restructured farmhouse where Top Guide Sandro and his family reside. The picturesque location in the characteristic Tuscan landscape outside of Siena is full of soft hills and beautiful scenery.
Molinello to Siena
Meals Provided
BreakfastAverage Mileage
37/39 milesElevation Gain
3000/3700 ftRiding Terrain
RollingMeals Provided
BreakfastSiena
Meals Provided
Breakfast, DinnerMeals Provided
Breakfast, DinnerSiena to Radda in Chianti
Meals Provided
Breakfast, LunchAverage Mileage
33 milesElevation Gain
3500 ftMeals Provided
Breakfast, LunchAccommodations
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.
Radda in Chianti Gravel Loop
Meals Provided
Breakfast, DinnerAverage Mileage
23/30 milesElevation Gain
2000/2300 feetRiding Terrain
Rolling on gravelMeals 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.
L'Eroica!
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
28/47/84 milesElevation Gain
2500/4900/7500 ftRiding Terrain
Superb !Meals Provided
Breakfast, 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.