Bike Tour for avid bikers

Our challenging bike trip from Pienza to San Gimignano; a combination of a lot – to enjoy a blast! The unique val d’Orcia and ideal renaissance town of Pienza, Montalcino the top wine brunello town, the medieval castello di Gargonza where you will be guest, cross Chianti Classico vineyards, “citta delle torri” or Tuscan Manhattan those are the nicknames of San Gimignano, Etruscan town Volterra.

All together in this self guided for experienced bikers – anyway the average is 60/70 km and allow time to visit all the sight along the way.

Available Carbon frame race bike, hybrid and high-end E-bike and Gravel


  • Breathe the history: Magical stay in Gargonza medieval castle, XV century convent in Pienza, renaissance palace in San Gimignano.
  • Oldest town in Tuscany Volterra founded before roman times!
  • Pecorino cheese, brunello wine & bruschetta -please spell brusketta.
  • Artisanal gelato tour

Do you prefer the guided version? Essence of Tuscany is the right bike tour


Pienza & Montepulciano

Arrive on your own to Pienza, the most perfect Renaissance town in the world. Meet & greet, bike-fitting session OPTIONAL short ride to Montepulciano and Monticchiello 35 km

Montalcino & Orcia valley

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...
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
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.
Total Distance 68 km/42 miles available longer ride via San Filippo and Abbadia 100km

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!
Total Distance: 57 km/35 miles. Available extension via Asciano

Chianti Wine & Abbeys: Castello di Brolio & Gaiole

Pedaling north, we'll whisk past a pair of typical southern Tuscany towns and make a stop at Castelnuovo Berardenga, the gate to Chianti Classico region, then pass through the vineyards, continue to Castello di Brolio winery, home of Barone Ricasoli and his world-renowned wine. Few miles more and we’ll get in Gaiole; stop in the village for a light lunch. Now face the climb to Badia a Coltibuono thinking only you will enjoy the beautiful downhill to Radda in Chianti. Now last 10 km up and down and get to your palazzo hotel with a spa. Before dinner we will be treated a terrific Chianti Classico wine tasting in a small winery.
Total Distance 64 km/40 miles - available extension to Monte Luco

San Gimignano & Monteriggioni

Ride to San Gimignano: more vineyards await us today, but you'll be amazed at how different they look once we get into the district of San Gimignano. Soon you pass Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Soft, colorful, rolling hills of vineyards and sunflowers provide the backdrop to pre-Roman Etruscan remnants on your route to San Gimignano’s "medieval skyscrapers” in the distance you will see the seventeen towers. You'll have plenty of time to wander through the cobblestoned streets, window shop and buy a few last-minute Tuscan mementos for our friends and...why not, for ourselves too!
Total Distance: 60 km/37 miles

Volterra & Etruscans

Today, you will leave San Gimignano behind and cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and villas, you reach the base of the imposing hill upon which the town is set. One more solid climb before you arrive in the old town. The “magic and mysterious” city of Volterra has its roots in three thousand years of history. It is possible to find evidence and traces from every historical period which gives the artistic city a unique aspect.
Total Distance 60 km / 37 miles

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Hotel Il Chiostro di Pienza
Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool.
Luxury upgrade in Pienza: Bandita Townhouse
La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. the property itself blends in completely with the Renaissance character, is a comfortable, and stylish place.
Castello di Gargonza
Castello di Gargonza is a thirteenth- century fortified village. Enclosed inside the medieval walls, the careful restored houses have retained the simplicity of rural life. Forest trails, relax in the Limonaia garden, sit at our bar with view of medieval tower and the woods surrounding the village
Palazzo Squarcialupi - Castellina
Palazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the XV century City Wall. Set in the spacious garden, in a most suggestive position, is the swimming-pool. The palazzo has medieval origins and it has been renewed becoming a luxury palace
Antico Pozzo - San Gimignano
Antico Pozzo the building, now completely restored,preserves the original style of the 15th century, although the earliest part dates back to the middle ages and the founding of the town itself:traces remain of the well and the area around it.
Luxury upgrade in San Gimignano: La Collegiata
Originally a Franciscan convent built in 1587, Hotel La Collegiata is located just 1 km from San Gimignano. Rooms are furnished in a style that reflects the Sienese Renaissance palaces and located in the former cloister. The top-floor rooms overlook the 13 towers of San Gimignano. Ample pool and beautiful, Italian-style garden opposite the ancient building.

Price & Inclusions

Cost: Euro 1690 per person in double occupancy
Single room supplement Euro 550

Six nights in excellent four & three-star superior hotels
Six breakfasts
One gourmet dinner
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Maps with elevation gain
Delivery bike at Pienza hotel & bike fitting
Pick-up of bikes and gear in San Gimignano
Keepsake Cicloposse water bottle
Sales taxes

Not Included
Bike Rental per entire tour
Hybrid bike euro 180
Race bike, E-Bike, Gravel         euro 240

City Tax   each village charges a tax per day between euro 0,70 to euro 3,00

Cooking lesson & Wine tasting

Tour Reviews

14 January 2018

Ciao Fernanda!
How nice to hear from you. You did great! We had a wonderful time on our trip. The Tuscany Challenge itineraries and routes were well laid out (with some great climbs and descents) and mostly easy to follow (my only suggestion would be more specific directions to the hotels once you arrive at the larger towns). The scenery, of course, was spectacular, and varied, giving us a real sense of the Tuscan countryside and its fascinating, charming villages. All of the hotels were excellent as were the recommended restaurants that we tried. The bikes were top-notch, with only one very minor mechanical issue (incorrectly calibrated computer and broken mount) which Gigi quickly and efficiently fixed. Gigi, in fact, was terrific in every way: personable, knowledgeable and caring – a joy to work with.
We would definitely choose Cicloposse again. Molto grazie!

30 November 2016

Hi Fernanda and all of Cicloposse,

I wanted to thank you all for the wonderful self-guided bike tour my wife and I did 2 weeks ago. I loved every second of it. The bikes were incredible and the directions were so easy to follow. The routes were great and the hotels were amazing. We look forward to riding with Cicloposse again next year.

Robert and Vanessa

18 October 2016

Hi Giuliana Gracias!!! What an amazing week of biking, food, great people & wonderful accommodation you organized for us. Loved every km of the cycling, scenery, towns & scrumptious food & wine at the end of the day. It has been an absolute pleasure dealing with you. Your friend Robert drove us to Florence airport, so we got to ride on the last morning as well. Oh, that vintage bike shop in Gaiole was fantastic & they ship to Australia – bonus! Take care

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