Heart of Tuscany Bike Tour

The quintessential Ciclismo Classico experience, and simply the best way to tour Tuscany.

There are few better ways to fully immerse yourself in this land of light, history, and vine than this quintessential Tuscany bike tour. Find yourself gliding down lanes gilded by the Tuscan sun for seven glorious days, as we bring you unforgettable cycling adventures in this most fabled of Italian regions.

From the quaint town of Radda in Chianti to the photogenic landscapes of San Quirico D’Orcia, our biking tour through the magnificent Tuscan countryside has, as its backbone, the famed Via Chiantigiana. Literally meaning “Chianti Street”, this most classic of Tuscany cycling routes reveals the heart of the Chianti wine region in all its splendor. Rich with color, all around are views worthy of a Renaissance painting—alive with bright wildflowers in the spring, darkened with crushed grapes in the fall.

Our Tuscany bike tour also features a visit to Siena, where a languid medieval air lingers amidst its twisting streets of warm ochre buildings. Strolling its narrow maze of cobblestone alleys you’ll make an amazing architectural journey. Explore delightful piazzas, intricate displays of masonry, and its superb marble cathedral, before climbing the Torre del Mangia, Siena’s most famous tower, to enjoy its breathtaking views.

Great Culture, Cuisine and Company on this Grand Tuscany Biking Adventure

Chianti is a wine practically synonymous with Italy itself, benefiting from an unparalleled terroir that nurtures the best in Italian reds—something you’ll quickly appreciate on our Tuscany cycling adventures. We’ll pedal first to Montalcino, hometown of the most famous Tuscan red, Brunello di Montalcino. We also track through Greve and Panzano, literally immersing ourselves in Chianti along the way!

Complemented by outstanding meals, you’ll also learn from the experts about the finer points of Tuscan cuisine, and its wonderful olive oils. Visiting the homes of renowned local producers (some of whom are your Ciclismo Classico guides) you’ll take part in cooking lessons in authentic Tuscan cuisine. We’ll also visit the UNESCO World Heritage Site of Val d’Orcia and ride the “Crete Senesi,” one of the most beautiful Tuscany bike routes.


  • Stay in Tuscany luxury hotels and countryside inns
  • Learn more about Tuscan cuisine, its wines and its olive oils, with exclusive visits to the homes of local producers
  • Memorable Tuscany cycling routes through the Chianti area
  • Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
  • Ride through the Crete Senesi on one of the most beautiful bike rides in Tuscany
  • Immerse yourself in an authentic Tuscan lifestyle with a traditional cooking lessons
  • Ride to Montalcino, home of the most famous Tuscan red wine: Brunello di Montalcino

Trip Details

Single Supplement
7 days / 6 nights
Total Mileage
174 miles
Daily Average
29 miles
Rolling and hilly with breathtaking views
Start/End Locations
Radda/San Quirico D'Orcia
Trip Dates
09/10/17 - 09/16/17
10/08/17 - 10/14/17
05/06/18 - 05/12/18
05/20/18 - 05/26/18
06/17/18 - 06/23/18
07/01/18 - 07/07/18
07/08/18 - 07/14/18
07/22/18 - 07/28/18
08/26/18 - 09/01/18
09/30/18 - 10/08/18
10/14/18 - 10/20/18

Make this tour Private or for more information, call:



Radda warm-up ride

On the first day of our splendid bicycle tour of Tuscany we will first gather together in the hotel lobby at 12:30 pm for a leisurely lunch, followed by a brief introductory talk. This will be your first chance to meet our local guides, experts in the region, and to discover more about delights in store while you’re biking in Tuscany.

After a customized bike fitting to ensure your comfort, the afternoon will be spent riding to Castellina in Chianti, with the lure of the town’s exceptional artisan ice cream adding vigor to our pace. For those who choose to indulge in more riding, there’s an optional loop up to Lucarelli, followed by a long, fun-filled descent down through the Chianti vineyards.

The Chianti

Today we ride on the Chiantigiana road through the Chianti region of Italy! Greve and Panzano in Chianti are the two destinations of our ride: we’re literally immersed in the Chianti, an exceptional wine that benefits from a great terroir, to create some of the best reds in Italy. Extra loop takes you to Badia a Coltibuono (Abbey of the Good Harvest), an abbey founded in 1051 by Vallambrosa monks


Today we leave the Chianti region for another beautiful ride and an extra loop to Castagnoli. We cycle to the medieval city of Siena. En-route we will stop for lunch and a wine tasting at the Felsina Vineyard. This afternoon, our friend Serena invites us to her family’s villa in the countryside where we will meet her family and learn to cook!

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, with an extra loop to Scorgiano, cuore della Montagnola Senese (heart of the Montagnola Senese).

Siena to San Quirico D'Orcia

We will ride through the “Crete Senesi,” a range of clay hills situated between Siena and the Val d’Orcia. Lunch today is at the home of our guide Sandro and his wife Elisa at their Agriturismo il Molinello, a family-run farm stay that combines agriculture and tourism. You’ll be treated to a traditional Tuscan cuisine and olive oil tasting. End the day with a final ride to San Quirico D’Orcia.

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.


After breakfast at 9 am we offer a 45-min group shuttle to Chiusi-Chianciano train station from where you can connect to Florence or Rome in less than 2 hours.

What's Included

Trip Planning

  • Use of a custom carbon bicycle, fully-equipped and featuring a Garmin Edge Touring GPS
  • Informative tour leaders on-hand throughout the program
  • Ciclismo Classico jersey and water bottle
  • Shuttle at the beginning and end of the tour

On The Tour

  • Van support
  • Guided tours in Siena
  • Olive oil tasting
  • Cooking lesson by local chef
  • 2 wine tastings

Accomodations & Meals

  • All Accommodations
  • All breakfasts
  • 4 lunches
  • 5 dinners

Meet the Guides