Challenge Tuscany bike tour

Challenge Tuscany bike tour

Challenge Tuscany bike tour

Tuscany - Self guided

Our challenging bike trip in Tuscany 

The unique val d’orcia and  ideal renaissance town of Pienza, Montalcino the top wine brunello, the medieval castello di Gargonza where you will be guest, cross chianti Tuscan  Vineyard, “citta delle torri” or Tuscan Manhattan  those are the nickname of San Gimignano, Siena the palio town

Wow Moments

#Breathe the history: Magical stay in Gargonza medieval castle, XV century convent in Pienza, renaissance palace in San Gimignano

#Pecorino cheese, brunello wine & bruschetta – please spell brusketta 

#artisanal gelato guide!

Bike Tour for avid bikers

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.


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 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, the old 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 potential next stop for a coffee or lunch break 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.

Distance: 70.6 km
+1391 m / -1396 m


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.
Cycling in the valley, 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 Castello Di Gargonza its magical! dinner included

Distance: 56 km
+978 m /  -951 m


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.

Distance: 64 km
+1156 m /  -1102 m


San Gimignano & Vernaccia

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 San Donato in Poggio, Tevernelle in val di Pesa and Barberino. You are in the florenting chianti
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!
Back to Castellina is shorter and be ready for the amazing uphill: this road from Poggibonsi is so quite immersed in a park

Distance: 76 km
+1236 m /  -1237 m


Medieval walled city of Siena

Start with long downhill to 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. After passing Casole d’elsa Let’s pedal through vineyards and forest we’ll arrive in Siena, a medieval city with beautifully preserved Gothic architecture.
The entire city of Siena was built around the Piazza del Campo. Here we’ll have time to shop while exploring the many hidden medieval walkways. Go soon to visit the shell shape square where the Palio horserace is run and enjoy a glass of super Tuscan wine at sunset . YOU DID IT!

Distance: 73 km
+1068 m / -1294 m


See you soon at next bike trip

Enjoy your breakfast at hotel garden and explore again this lovely walled town

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Tour start in Pienza
Tour end in Siena

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best period From March to End of October


TOTAL DISTANCE : 340 km/ 212 miles in 5 stages



Tour Reviews

14 January 2018

Ciao !
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


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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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 Siena
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

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

Villa di STR

Villa STR is a converted 19th-century villa that retains the charm and ambiance of its former origins as a private residence.
The decoration in the recently renovated public areas bears the hallmarks of Italian classical design, with a quiet Garden for relaxing .
Hotel is a 10-minute walk from Piazza del Campo

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