Tuscany and L’Eroica
A memorable flashback to the heroic times of cycling
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- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
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Experience the beauty of Tuscany over a seven-day journey, savoring the picturesque roads, delicious food, and exquisite wines. Travel from the serene countryside of Serre di Rapolano to the Chianti region via the Val d’Orcia, where
a charming atmosphere fills the twisting streets lined with warm, brown brick buildings. Each day, you’ll pedal through olive groves and vineyards, immersing yourself in the nostalgia of old-time cycling, culminating in the grand finale at the “L’Eroica, Gaiole” vintage cycling festival. Join cyclists from around the globe in Gaiole as you ride the iconic white gravel roads of Tuscany, sharing in a day of epic sport, camaraderie, and enjoyment.
Tour Essence
- Participate in L’Eroica, the world’s greatest cycling event
- Stay in exclusive luxury hotels and countryside inns
- Cycle through the UNESCO World Heritage site of Val d’Orcia
- Learn about the production of olive oil
- Indulge in traditional Tuscan cuisine
- View our Top Photos from Tuscany and L’Eroica
What to Expect
Terrain
Rolling and hilly with breathtaking viewsStart Location
Serre di RapolanoEnd Location
Radda in ChiantiMileage
Average Daily: 28/38 miles Total: 170/230 milesElevation
Average Daily: 2,450/3,750 ft Total: 14,700/22,500 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
- Expert, bilingual guides
- 1 wine tasting
- 1 Tuscan cooking lesson
- 1 olive oil lesson
- Guaranteed entrance to L’Eroica
- Van support
- Shuttle at the beginning and the 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 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, and 5 dinners
Start Location
Serre di RapolanoFly Into
Florence (FLR)End Location
Radda in ChiantiFly Out Of
Florence (FLR), or Rome (FCO)Serre di Rapolano Warm-up Ride
Meals Provided
Lunch, DinnerAverage Mileage
13 milesElevation Gain
900 ftRiding Terrain
RollingMeals Provided
Lunch, DinnerAccommodations
Agriturismo Il Molinello
Agriturismo Il Molinello is a renovated farmhouse where our Top Guides, Sandro and Guido, live, offering a back-to-nature experience. Gentle hills and stunning scenery surround the beautiful location in the characteristic Tuscan landscape outside of Siena.
Val D'Orcia Loop to Pienza
Meals Provided
Breakfast, DinnerAverage Mileage
38/50 milesElevation Gain
3,300/4,100 ftRiding Terrain
Rolling with 2 main climbsMeals Provided
Breakfast, DinnerAccommodations
Agriturismo Il Molinello
Agriturismo Il Molinello is a renovated farmhouse where our Top Guides, Sandro and Guido, live, offering a back-to-nature experience. Gentle hills and stunning scenery surround the beautiful location in the characteristic Tuscan landscape outside of Siena.
Montalcino
Meals Provided
Breakfast, DinnerAverage Mileage
35/53 milesElevation Gain
2,600/4,200 ftRiding Terrain
Lots of ups and downs and some solid climbsMeals Provided
Breakfast, DinnerAccommodations
Agriturismo Il Molinello
Agriturismo Il Molinello is a renovated farmhouse where our Top Guides, Sandro and Guido, live, offering a back-to-nature experience. Gentle hills and stunning scenery surround the beautiful location in the characteristic Tuscan landscape outside of Siena.
Radda in Chianti
Meals Provided
Breakfast, LunchAverage Mileage
33 milesElevation Gain
3,500 ftRiding Terrain
Rolling with two main climbsMeals 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
2,000/2,300 ftRiding 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
2,400/4,900/7,500 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.
