Ride with us in Tuscany!

  Beautiful Val d’Orcia and the sublime city of Siena

The Val d’Orcia, one of UNESCO’s World Heritage sites, evokes a kind of fairy tale air with character-filled small towns in perfectly preserved historic centres. They still  narrate the rich cultural history of bygone times. As you ride through the surrounding Pinterest-perfect countryside, with its undulating hills dotted by fields of sun kissed sunflowers, you get up-close and personal with local Tuscan culture. Enjoy a healthier you, thanks to the best local produce, world-class wines and a variety of olive oils from one of the world’s capitals of food & wine.

Take in the beauty of art treasures found in the city of Siena, like artist Ambrogio Lorenzetti’s famous cycle of frescoes – “The allegories and effects of good and bad government’ – which highlight the Aristotelian principle that only justice and common good can ensure peace and prosperity for the State. These frescoes were commissioned at a time when the Republic of Siena was one of the most powerful of the fourteenth century Italian city-states. This was also the city of Saint Catherine, born in 1347, she was the most important woman of the Middle Ages.

Tip toe into the secluded world of the working Abbey of Monte Oliveto Maggiore and admire the ancient library, apothecary, cloisters and church adorned by works of many Renaissance masters, including della Robbia, Signorelli and Sodoma. Or be tempted by the liqueurs produced by the Abbey’s monks, who in accordance with age-old recipes are preserving the tradition of transforming simple herbs and fruits into potions that seemingly cure a number of ailments.

Connect with the culture and people of Tuscany!

Non-cycling friends and partners welcome

If you’re travelling with a non-cycling partner or family, they have the option to participate in cooking classes, art workshops or  sightseeing. Contact us with your requirements, we’ll be happy to offer some great solutions.


  • A full immersion in the magnificent valleys of the Val d’Orcia and Siena
  • A unique insight into the culture of Brunello and other distinguished wines
  • Visiting local winery NostraVita
  • A guided walking tour of the city of Siena
  • A private cooking class with a Tuscan chef-instructor
  • Entering the secluded world of the working monastery of Monte Oliveto Maggiore
  • Dining at authentic and off-the-beaten-track restaurants

A  day by day itinerary

Route (15km):

Val d’Orcia > Pienza > Val d’Orcia

After a warm welcome from your bike tour leader it’s time  for a professional bike-fitting.  Soon after we set out on a 15km warm-up ride to Pienza.  Reward yourself at  Piccolomini Café with some of the local delicacies: bruschettas, freshly made pastas, cured meats and the famous pecorino cheese.

Pienza is a tiny jewel, the perfect Renaissance city, designed by native Pope Pio II. With a spectacular Duomo, featuring gothic design, the historic centre of the city is a UNESCO World Heritage site. It lies atop a hill with a circular path around the town walls, offering magnificent 360-degree views of the valley. Not to be outdone, its streets have romantic names, like ‘Via dell’amore’, echoing the concept of an ideal city.

Route (60km):

Spedalone > San Quirico > Montalcino (stop-over with coffee) > Torrenieri > San Giovanni d’Asso > Montisi > Castelmuzio > Spedalone

Today  we make our way to Montalcino, a feast for the senses with vineyards and open fields. It is the area where some of Italy’s most exquisite wines are produced.  We continue our ride to the small village of Montisi, its name is believed to have come from a nearby temple, which is dedicated to the goddess Iside (worshipped by the Etruscans).

After a peaceful siesta we  visit the wine estate of ‘NostraVita. Its name translates to ‘Our Life’, in celebration of the vision Annibale Parisi and his wife Elena had for the property when they bought it in 1970. It’s located in an area of prime significance in Italian viticulture – a gentle wooded hill between the historic town of Montalcino and the ancient Abbey of Sant’Antimo. The 2-hour tour includes a complimentary wine-tasting of Brunello and Rosso di Montalcino.

Route (55km):

Spedalone > Pienza > Monticchiello > Montepulciano > Pienza > Spedalone

With Pienza behind us, we begin to see the beautiful medieval village of Montichiello, nestled in the rolling Tuscan landscape. Perched high on a hill overlooking the valley, it offers absolutely stunning views across the valley to Pienza. Next the town of Montepulciano. It sits high atop a limestone ridge, on Monte Poliziano, in Tuscany’s Vino Nobile wine region. The area is renowned for its red wines, especially the Nobile di Montepulciano, one of the most appreciated wines in all of Italy.

Route (65km):

Spedalone > Monte Oliveto > Asciano, crete senesi and Siena

As we venture across the drawbridge into the working Monastery of Monte Oliveto Maggiore, history embraces you. A wide avenue beyond the gatehouse leads to the impressive Gothic façade of the church. The route is marked by botanical gardens on one side and Tuscan cypresses on the other. The tower, library, apothecary, cloisters and church are adorned by works of many Renaissance masters including della Robbia, Signorelli and Sodoma. According to locals living in the Tuscan region of Le Crete, the area surrounding the Abbey of Monte Oliveto Maggiore abounds in inexplicable positive energy. Since 1319 the monks have been transforming simple herbs and fruits into liqueurs that seemingly restore all sorts of ailments! From Monte Oliveto, we continue on to Asciano, where we marvel at the Crete Senesi (Senese clays), an area that between 2.5 and 4.5 million years ago was covered by the Pilocene sea.

We stop for lunch before heading towards Siena, which will be our home for the next few days.

Route (0km):

Today we explore the magnificent city of Siena

After four days of good riding, it’s time for some cultural immersion with  a 2-hour guided walking visit of the city of  Siena. Our guide will take you along quaint narrow streets, passing by fragrant bakeries, art workshops and unique specialty shops.

Route (55km):

Tenuta di Monaciano > Radda in Chianti > Tenuta di Monaciano

Today we ride towards Radda in Chianti, inhabited since the 9th century, it retains the characteristics of a Medieval town. After a walk around town, it’s time for a complimentary wine tasting of the Chianti Classico DOC accompanied by a selection of premium meats and cheeses from the best producers in the area.

Route (0):

Artisan food specialties and tastings
Today  we’ll visit an artisan who excels in the art of cheese making. Our local Tuscan guide will unveil the secret of what makes Tuscan food so special. The rest of the day is for you to enjoy. In the evening time to meet up for some celebratory dinner and drinks.

Eat & Ride Getaway

Location: Val d’Orcia, Siena
Type of Tour: Private Bike Tour
Length: 7 days
Level: Intermediate (you must able to ride 3-4 hours per day)
Distance: 250 km
Start: Val d’Orcia
Finish: Siena
Accommodation: Charming Boutique style, twin share
Price: Quoted to you at the time of request



During the Tour
  • Bike tour with local and highly experienced tour leader
  • Guided walking tour of Siena
  • Food snacks during tour
  • Complimentary wine-tasting at family-owned winery
  • Wine-tasting in Radda in Chianti region
  • Visiting local food artisans
Support and Planning
  • Support van throughout tour
  • Baggage drop-off from Val d’Orcia to Siena
  • Two shuttle services, return trips to Siena
  • Bike rental equipped with odometer, seat bags and bike pump, small rear bag with spare tube and tire iron, water bottle and bike helmet