Heart of Tuscany

The Quintessential Ciclismo Experience in Our Home Away From Home.

From the quaint town of Radda in Chianti to San Quirico D’Orcia, Tuscany’s cultural wealth and natural beauty are incredibly rich and varied. Immerse yourself in the Tuscan countryside along Via Chiantigiana (literally, Chianti Street), a classic and rustic route that passes through the heart of the Chianti wine region. The landscape is like a Renaissance painting that comes alive with wildflowers in the spring or crushed grapes in the fall. Our cycling excursion also features a visit to Siena, where a medieval air lingers amidst the twisting streets of warm, brown brick. Strolling Siena’s narrow maze of cobblestone walkways is an amazing architectural journey – with its incredible masonry, delightful piazzas, a marble cathedral, and Torre del Mangia, Siena’s famous tower, with a view that will make your head spin!

Our bicycling journey in Tuscany will bring us through the UNESCO Site of Val d’Orcia, usually depicted in postcards epitomizing the typical Tuscan countryside, before the great finish in Pienza, known for its charm and beautiful layout, one of Tuscany’s best-preserved medieval cities.

This tour is quintessentially the best of Tuscany and allows you to experience for seven days the real life “under the Tuscan sun!


  • 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, Siena and Pienza
  • 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

Trip Details:

Biking Culture Italio-

Price: $4,295

Single Supplement: $800

Length: 7 days / 6 nights

Level: Intermediate

Total Mileage: 174 miles

Daily Average: 29 miles

Terrain: Rolling and hilly with breathtaking views

Start/End Locations: Radda/Pienza

Trip Dates:

  • 05/03/15 - 05/09/15
  • 05/17/15 - 05/23/15
  • 06/14/15 - 06/20/15
  • 06/28/15 - 07/04/15
  • 07/05/15 - 07/11/15
  • 09/06/15 - 09/12/15
  • 09/20/15 - 09/26/15

= Sold Out

Make this tour Private or for more information, call:


Day by Day

Radda warm-up ride

We will get together at 12:30 pm in the hotel lobby for lunch and a brief introduction talk. In the afternoon after a bike fitting we will ride to Castellina in Chianti to taste an exceptional artisan ice cream. An optional extra loop will take you to Lucarelli followed by a long and fun descent immersed in 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

  • Bike rental equipped with odometer, map case, handlebar and seat bags and bike pump
  • Ciclismo jersey and water bottle
  • Shuttle at the beginning and end of the tour

On The Tour

  • 3 cycling clinics
  • Guided tours in Siena
  • Olive oil tasting
  • Cooking lesson by local chef
  • 2 wine tastings

Accommodations & Meals

  • All Accommodations
  • All breakfasts
  • 5 dinners
  • 4 lunches
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. It dates back to the 17th century and has been carefully restored, maintaining the atmosphere and charm of an elegant country manor house. 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