Tuscany and L’Eroica
A Southern Tuscan Spin paired with an Unforgettable Taste of Vintage cycling at its Best
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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 miles
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
- 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 a carbon road bike equipped with a Garmin Edge GPS
- Vintage bike rental for the Eroica
- Ciclismo Classico jersey and water bottles
- Handlebar bag
- Tire pump
- Combination bike lock
- Gel-padded saddle
- Choice of pedals
- Card with your tour leaders’ mobile phone numbers
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless 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
2022
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
BreakfastAccommodations
Hotel Palazzetto Rosso
Set in a redbrick building dating from the Middle Ages, this eclectic hotel is a 2-minute walk from the domed church of Santa Maria in Provenzano, a 6-minute stroll from the buzzy Piazza del Campo. Furnished in a contemporary style, the 9 rooms feature elements such as exposed ceiling beams, brick walls or terracotta floors. All come with air-conditioning, flat-screen TVs and free Wi-Fi. Suites add living areas (some with pull-out sofas) and/or fireplaces. Some quarters offer city views.
Siena
Meals Provided
Breakfast, DinnerMeals Provided
Breakfast, DinnerAccommodations
Hotel Palazzetto Rosso
Set in a redbrick building dating from the Middle Ages, this eclectic hotel is a 2-minute walk from the domed church of Santa Maria in Provenzano, a 6-minute stroll from the buzzy Piazza del Campo. Furnished in a contemporary style, the 9 rooms feature elements such as exposed ceiling beams, brick walls or terracotta floors. All come with air-conditioning, flat-screen TVs and free Wi-Fi. Suites add living areas (some with pull-out sofas) and/or fireplaces. Some quarters offer city views.
Siena to Radda in Chianti
Meals Provided
Breakfast, LunchAverage Mileage
33 milesElevation Gain
3500 ftMeals Provided
Breakfast, LunchAccommodations
Palazzo Leopoldo
Palazzo Leopoldo is a wonderful villa in 1800 style in the historical center of Radda in Chianti. The building dates back to 1300.
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
Palazzo Leopoldo is a wonderful villa in 1800 style in the historical center of Radda in Chianti. The building dates back to 1300.
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
Palazzo Leopoldo is a wonderful villa in 1800 style in the historical center of Radda in Chianti. The building dates back to 1300.
