Tuscany and L’Eroica Bike Tour

A memorable flashback to the heroic times of cycling.

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.

The 2017 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 gran 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.


  • 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!)
  • Memorable rides in the Chianti area
  • Discover the UNESCO World Heritage Site 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

Trip Details

Single Supplement
9 days / 8 nights
Total Mileage
250 miles
Daily Average
31 miles
Rolling and hilly with breathtaking views
Start/End Locations
Serre di Rapolano/Radda
Trip Dates
 09/30/17 - 10/02/17
09/30/18 - 10/08/18
= Sold Out

Make this tour Private or for more information, call:



Serre di Rapolano; warm-up ride

Welcome to Tuscany! Upon arriving to Asciano, we will have an intro lunch to get everyone acquainted with each other and get to know your guides, Sandro and Marcello.

We will have a bike fitting and a rolling warm-up ride in the hills of Asciano, where olive groves and travertine quarries dominate the landscape, with a refreshing stop by a local microbrewery.

Val D'Orcia with loop to Pienza

Today, we'll ride in Val d’Orcia, considered one of Italy’s wonders and a UNESCO World Heritage site. Medieval castles, sunny rolling hills, isolated hilltop towns, olive groves, and golden wheat fields are just some of the elements that make its landscapes so fantastic! We'll stop in Pienza for a stroll through town, where you'll get to see its famous art and historical monuments. Later on in the day, we'll have an olive oil lesson.


Today, we'll ride to Montalcino, the city of the famous wine Brunello di Montalcino DOCG. Once you arrive, a magnificent spectacle unfolds before your eyes: rolling, sunny hills dotted with yellow and red flowers, picturesque olive groves, and scenic country roads winding through perfect vineyards. Later on, we'll have a picnic lunch at Giuditta Parisi’s (one of your guides) farmhouse, Nostra Vita winery, where they produce Brunello di Montalcino DOCG. Once we get back to Molinello, we'll enjoy a night of cooking, music, and savory and authentic Italian cuisine!

Molinello – Asciano – Monteroni – Siena with extra loop to Murlo

We'll ride through the “Crete Senesi,” a range of clay hills situated between Siena and the Val d’Orcia. With its ever-changing seasonal colors, its winding roads and the lunar landscape of its clay ridges, this ride is considered a cycling classic in this part of Tuscany. There will also be an Italian lesson and dinner will be at Taverna di San Giuseppe.


Today, you can either rest or do a loop ride out of Siena to the medieval walled town of Monteriggioni in the morning, with an extra loop to Scorgiano, cuore della Montagnola Senese (heart of the Montagnola Senese). In the afternoon, our local guide will take us all on a guided tour of Siena, which is also a UNESCO World Heritage site.

Radda in Chianti

Today, we'll ride from Sienna to Radda, stopping for a Ciclismo Classico scenic picnic in Castagnoli along the way! There will also be an optional loop to Lecchi.

Pre-race day; Radda in Chianti

We'll have a ride in one of the most famous regions in Italy: The Chianti. Riding along some white roads will give you a completely different perspective of the area and of cycling as a whole, which will be the perfect introduction to L’Eroica. You'll also have a free afternoon in Gaiole/Radda to explore to your heart’s content!


The ride starts and ends from the historic center square of Gaiole in Chianti, where you’ll ride with more than 5,000 other cyclists experiencing the thrill of L’Eroica. You’ll be fueled and rewarded by stunning views of the Chianti hills, the town of Montalcino, Crete Senesi—and more! You’ll also pass miles of vineyards where the annual grape harvest will be taking place. After the ride, we'll have dinner at La Botte di Bacco. For non-riders, the day will be a great opportunity to enjoy the Eroica expo, stroll through Gaiole, wander around the lovely roads and stop at a quaint viewpoint to cheer on the riders!


The tour ends after breakfast around 9 a.m. We provide a shuttle to Montevarchi train station, where you can connect to Florence or Rome.

What's Included

Trip Planning

  • Use of a carbon road bike equipped with a Garmin Edge Touring GPS
  • Informative tour leaders throughout the program
  • Ciclismo jersey and water bottle (vintage wool jersey also available)
  • Shuttle at the beginning and end of the tour

On The Tour

  • Van support
  • Guided walking tour in Siena
  • 2 wine tastings
  • 1 Tuscan cooking lesson, 1 olive oil lesson, and 1 Italian lesson
  • Guaranteed entrance to L'Eroica

Accomodations & Meals

  • All accommodations
  • All breakfasts, 3 lunches, and 6 dinners

Meet the Guides