Once in a lifetime cycling experience.

Join us on this total immersion into Tuscany tour: back roads head into rolling hills and through the fortified medieval villages of an untouched Toscana. Goal of the bike trip is also enjoy the genuine tuscan cucina: fruity olive oil, pecorino sheep-milk cheese and classic best Tuscany wine:
Brunello, that has made Tuscany so famous, Chianti Classico and Nobile.

You will taste a selection of our favorite producers during our special events.
Traveling with a small group of fellow adventurers and Tuscany’s leading biking guide, you’ll enjoy a wonderful combination of nature, culture, cuisine and fun.


Day by Day

1° Pienza ‘the perfect town’

Meet at Chiusi-Chianciano train station at 12.00 pm (a stop on all major Florence-Rome lines).
Transfer to Pienza, the most perfect Renaissance town in the world.
Check into your rooms at your hotel, which occupies a 15th-century convent in the center of town.
At 3.00pm Meet your guides during a bike-fitting session and get to know the rest of the group. OPTIONAL (depends on weather conditions and on time taken in the bike fitting) Short ride to Bagno Vignoni: The ancient village is located in the heart of Tuscany, in the Val d’Orcia Natural Park. Thanks to the Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), these thermal waters were found and have been used since Roman times. The heart of the village is the “Square of sources”, namely a rectangular tank of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins.
Welcome dinner in the wonderful La bandita townhouse Pienza, where you will taste special homemade pasta.

2° Montepulciano & Montichiello

Loop ride to Montepulciano and Monticchiello. Level: Moderate to challenging
Start your day with a pleasant downhill, You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval village. This is where “the English Patient” was filmed. Among the sites you’ll ride through there are the hilltop villages of Castelmuzio and Petroio.
Today’s ride will take you to Montepulciano, which is famous for the production of Vino Nobile di Montepulciano. After a stroll about the medieval streets of this village, you can stop to visit one of the typical wine cellars in town, the oldest one which is situated under the Ricci Palace.
Back to Pienza through Monticchiello, another hilltop village!
Total Distance 55 km/ 34 miles

3° Montalcino Brunello Land

Loop ride to Montalcino
Today we’ll start out on a long descent into the rolling green pastures of the Val d’Orcia: You are now at Parco Naturale e Artistico della Val d’Orcia, an Unesco site with this main justification: “ The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures.” Imagine cycling up and down in a scene from painting… Along the way face the hearty uphill to Castiglione d’Orcia, with the imposing Rocca A Tentennano. After a rest, enjoy a long downhill to Sant’Antimo Abbey , your next stop: if you have luck, you will hear the monks chanting. On your way to the Etruscan village and wine town of Montalcino you’ll pedal through magnificent vineyards. It is a fortified town which was used as a shelter by Siena nobles during the 16th Century. Today it is even more famous thanks to the production of one of Italy’s premier fine red wines, Brunello di Montalcino. Back to Pienza via San Quirico d’Orcia: stop in the village at Horti Leonini Garden, the top attraction of town.
Special event: Wine Tasting at Ciacci Piccolomini
Free dinner in town
Total Distance: 68 km/42,5 miles

4° Le crete & Castello di Gargonza

Le crete, Castelmuzio, Trequanda, Lucignano
Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque road, you’ll ride by Castelmuzio, Trequanda. Afterwards, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands, with strange rock formations and lone farmhouses flanked by twin cypress trees. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere. Cycle in the valley for a while and reach Lucignano, a small village that represents one of the more extraordinary examples of medieval urban planning for its system of elliptic rings arrived intact over the centuries.
Destination is a real castle restored – its magical!
Dinner at your Castello di Gargonza
Total Distance: 57 km/35 miles

5° Chianti wine & Abbeys

Castelnuovo Berardenga, Castello di Brolio,
Pedaling north, we’ll whisk past a pair of typical southern Tuscany towns and make a stop at Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlet. Not-to-be-missed is Castello di Brolio, a castle and winery, home of Barone Ricasoli and his world-renowned wine. Enjoy the up and down and get to your country resort hotel. Before dinner we will be treated a terrific Chianti Classico wine tasting in a small winery: Felsina
Dinner at resort.
Special event: Chianti Classico wine tasting at Felsina
Total Distance 50 km / 31 miles

6° Gaiole, Radda & Ama

Circular bike ride to heart of chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany’s forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil. We’ll stop for lunch in Gaiole, a lively town located along the river Massellone and home to the annual l’Eroica vintage (pre-1987 steel frame) bicycle race. A few more miles bring us to Radda in Chianti and the way back on the so called via dei Castelli not to be missed the stop at Castello di Ama to visit the winery and the borgo. Relax by the vanishing edge pool spilling into the countryside of endless vineyards
Farewell dinner at your resort.
Total Distance: 62 km/39 miles

7° Arrivederci

Enjoy the farewell breakafst and wander in Siena!

Price & Inclusions

Cost: Euro 2,650 per person in double occupancy
single room supplement euro 490

Six nights in superior hotels with private bath and breakfast
Four dinners, one lunch & two wine tastings
Snacks and drinks along the way
All maps, trip notes and detailed route directions
All Shuttles and technical assistance
Van Support, all baggage transfers
Experienced english speaking guides
Cicloposse water bottle
Sales taxes

Not included
Airfare to Italy, train to Chiusi, transfer on Day 7, 5 lunches, 2 dinners, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.

Bike Rental per entire tour
Hybrid bike euro 180
Race bike     euro 210
E-Bike         euro 210


Guided tour
rolling hills and some climbs, rarely flat
Spring and Fall


  • May 25th to 31st
  • July 13th to 19th
  • September 21st to 27th
  • October 19th to 25th


from minimum 4 people we can organize the tuscany tour on the dates you prefer



Hotel Il Chiostro di Pienza
Castello di Gargonza
Villa Curina – Castelnuovo



  • Full immersion in Val d’Orcia
  • Stay in Pienza the ideal renaissance city
  • Magical stay at a real medieval castle Gargonza
  • Riding through scenic landscapes where “English Patient” and “Gladiator” were filmed
  • A private tour of the cantina of Brunello in Montalcino, the emergent Le Ragnaie
  • Enjoy Chianti resort with wine and food focus
Book this tour