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.

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.


  • 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

Trip Details

Single Supplement
9 days / 8 nights
Total Mileage
207 miles
Daily Average
30 miles
Rolling and hilly with breathtaking views
Start/End Locations
Serre di Rapolano/Radda
Trip Dates
09/29/19 - 10/07/19

Make this tour Private or for more information, call:



Serre di Rapolano Warm-up Ride

Welcome to Tuscany! Upon arrival to Asciano with our 11:30 am group shuttle from Terontola, we’ll have an intro lunch to get everyone acquainted with each other and get to know your guides, Sandro and Marcello. We’ll have a bike fitting and a rolling warm-up ride in the hills of Asciano, where olive groves and travertine quarries dominate the landscape.

Val D'Orcia with Loop to Pienza

Today, we’ll plunge into Val d’Orcia, considered one of Italy’s wonders. Val d’Orcia was listed as a UNESCO World Heritage Site. Medieval castles, sunny rolling hills, isolated hilltop towns, charming isolated rural homes, and golden wheat fields are just some of the elements of the fantastic landscapes of this area.

We’ll stop in Pienza for a stroll through town and lunch is on your own. Pienza is famous not only for its beauty, art, historical monuments, but also for its Pecorino cheese. In the late afternoon at Il Molinello, you’ll have an olive oil tasting course with Sandro, who’s an official ONAOO taster and EVOO producer.


Today, we’ll have a ride that will lead you to Montalcino, the city of the famous wine Brunello di Montalcino DOCG. We’ll ride along the Pecorile road in the heart of Crete Senesi and the Asso Valley. Montalcino, renowned all over the world for the production of its precious Brunello red wine, has changed very little in appearance since the 16th century. We’ll have a picnic lunch at Giuditta Parisi’s (one of our guides) farmhouse, Nostra Vita winery, where the Parisi’s produce Brunello di Montalcino DOCG. There will also be a cooking lesson, music, and dinner later on back at Molinello!

Molinello – Siena

Today 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, 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 tonight.


Today will be a well-deserved rest day. In the morning, you’ll have the opportunity to do an ‘urban’ hike, which will allow you to explore Siena (a UNESCO World Heritage Site) and its secret corners. You could also see the underground river La Diana or visit Palazzo Pubblico. Lunch will be on your own, and you’ll have a free afternoon in Siena to do some more exploring or strolling. Tonight we will have a complete cooking class with dinner in a private Tuscan home.

Radda in Chianti

Today we’ll ride from Siena to Radda entering the Chianti Classico region. We’ll ride along Castello di Brolio, built around 1000 AD and owned since 1141 by the Ricasoli family, the oldest winery in Italy and the second oldest in the world. We will stop for lunch in Gaiole, starting to experience in the unique atmosphere of the Eroica.

Radda in Chianti Loop

Today we’ll have a ride in one of the most famous regions in Italy: The Chianti. We’ll get acquainted with our vintage bikes and give them a test ride on some sections of the gravel roads of L’Eroica. Riding along some of these roads will give you a completely different perspective of the area and of the idea of cycling as a whole. It will be the perfect introduction to L’Eroica. Lunch will be in Gaiole. You’ll also have a free afternoon in Gaiole/Radda to explore to your heart’s content and wander through the vintage market of the area.


The ride starts and ends from the historic center square of Gaiole in Chianti, where you’ll ride with more than 7,000 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 a celebratory group dinner.


The tour ends after breakfast around 9 am. We'll 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 and vintage bike rental for the Eroica
  • Informative tour leaders throughout the program
  • Wine kitty and Ciclismo kit (bib and vintage wool jersey [when available])
  • Shuttle at the beginning and end of the tour

On The Tour

  • Van support
  • 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