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 town of San Quirico D’Orcia to the Chianti area, along Via Chiantigiana (literally, “Chianti Street”), passing through medieval Siena, where an air lingers amidst the twisting streets of warm, brown brick, that you can see from the top of the Torre del Mangia, Siena’s famous tower.

This trip is a journey in search of the authentic cycling routes made famous by the giants of the roads. Together, immerse yourselves in the spirit of “L’EROICA”, a special “race” celebrating the “heroic” times of cycling with vintage refreshments and wonderful but demanding white gravel roads.


  • 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
  • Ride to Montalcino, hometown of the most famous Tuscan red wine, the Brunello di Montalcino
  • Experience riding on the “strade bianche”, terrain of the Eroica

Trip Details:

Biking Italio-

Price: $5,495

Single Supplement: $900

Length: 9 days / 8 nights

Level: Intermediate

Total Mileage: 180 miles

Daily Average: 30 miles

Terrain: Rolling and hilly with breathtaking views

Start/End Locations: San Quirico D'Orcia/Radda

Trip Dates:

  • 09/24/17 - 10/02/17

Make this tour Private or for more information, call:


Day by Day

San Quirico D'Orcia Warm-Up Ride

Today we will get together at 12:30pm in the hotel lobby for lunch and a brief introduction talk. In the afternoon after a bike fitting and warm-up ride to Pienza, a quintessential Tuscan town: benvenuti in the heart of Tuscany!

Loop to Montalcino

Today we ride in the UNESCO Site of Val d’Orcia. We’ll ride to Montalcino, hometown of the famous Brunello di Montalcino Tuscan red wine. After lunch we head to the home of our guide, Giuditta, whose family owns a small winery called Nostra Vita. After the wine tasting the extra loopers ride to Pienza while the rest of the group heads back to the hotel.


En route to Siena today we discover the lunar landscape of the “Crete Senesi” which consists of a range of hills situated in a specific area of the Province of Siena. We stop for lunch and olive oil tasting at an agriturismo, a family-run “farm stay”. Tonight we have a cooking class with our host Serena and her family.

Siena & Monteriggioni Loop

Today is a rest day in Siena. There is an optional loop ride out of Siena to the medieval walled town of Monteriggioni in the morning. We will have an afternoon walking tour with our local guide Nicoletta and will discover the Medieval atmosphere of this unique town.

Radda and the Chianti area

Today we enter the famous Chianti area riding on the Chiantigiana road,” through Castelnuovo Berardenga and Castello di Brolio, where we stop for a tour and wine tasting before we make our way to Radda.

Panzano and Greve in Chianti Loop

Today’s ride offers an intense experience of the Chianti hills; uphills and downhills surrounded by miles of vineyards where we’ll witness the harvest.

Pre-Race Day

The eve of the ride is an important one: final prepping of our bikes, a relaxed ride around Gaiole to get to know your vintage bike before the big day. We’ll also make sure we complete our intake of carbs and proteins for the event, relying on Tuscan specialties such as Ribollita, Pici and some Chianti wine.


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. The route is a challenge, yet you’ll be fueled by stunning views of the Chianti hills, the town of Montalcino, Crete Senesi—and more! 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 am. We provide a shuttle to Montevarchi train station from where you can connect to Florence or Rome.

What's Included

Trip Planning

  • Carbon bike rental equipped with Garmin Edge Touring GPS
  • Informative tour leaders throughout the program
  • Ciclismo jersey and water bottle
  • Shuttle to the beginning and at the end of the tour

On The Tour

  • Van support
  • Guided walking tour in Siena
  • 2 wine tastings and 1 olive oil tasting
  • 1 cooking class
  • Guaranteed entrance to L'Eroica

Accommodations & Meals

  • All Accommodations
  • All breakfasts
  • 3 lunches
  • 6 dinners
Here’s a sampling of some of the amazing places you’ll stay on your journey.

For a full listing, request a detailed itinerary!

Relais Vignale

The 4-star Relais Vignale is situated in the heart of the Chianti Classico region. The hotel is air conditioned, has a beautiful pool and gardens, and a panoramic terrace to view the Tuscan countryside. Dinner is included.
View their website

Hotel Athena

Hotel Athena is a 4-star hotel with views of the surrounding countryside and rolling hills. It’s located in the heart of the old town center inside the ancient city walls.
View their website


The beautiful 3-star Casanova is located in the Val D’Orcia area. In addition to a restaurant, this hotel features an outdoor tennis court, spa, and bar/lounge.
View their website

Meet the Guides