Cycling Tuscan Wine Country

Cycling Tuscan Wine Country

Cycling Tuscan Wine Country

Tuscany - self guided

Cycling with Tuscany Around

Experience the Essence of Tuscany’s Wine Culture

Yes, there are hills to conquer, but these ascents lead to unforgettable rewards amid Tuscany’s sunny Mediterranean aura and its vibrant hospitality. In this journey, Tuscany nourishes the soul and elevates your spirits with life’s earthly pleasures.


Wow Moments

#Journey into the heart of Chianti—and back in time—to sensational Siena and Castelllina

#Shadow the hilly course of L’Eroica, Tuscany’s internationally recognized vintage bike race

#Delight in Tuscan wines within ancient cellars, savoring Vino Nobile di Montepulciano and Brunello di Montalcino


Discover a Journey through Tuscany’s Iconic Wine Regions

Venture into the heart of three renowned wine areas that have propelled Tuscany to oenological fame.
Pedal through the rolling hills adorned with Sangiovese vines, each turn revealing a breathtaking landscape. Here, vineyards seamlessly blend with olive groves, vegetable gardens, and verdant woodlands. Amidst this tapestry of biodiversity, Tuscany’s commitment to organic and biodynamic principles shines brightly.


Explore Beyond the Vineyards

Embrace the authentic essence of the region, where history whispers from ancient monasteries nestled in secluded valleys and medieval forts dotting the horizon.
The carefully selected route weaves through tranquil country lanes, linking farmland adorned with walled villages, and offering stays in quintessential Tuscan towns like Pienza, Montalcino, Siena, and the heart of Chianti.

Savor the Flavors of Tuscany

After days spent amidst rolling vineyards, golden wheat fields, and chalky white hills, indulge in the culinary delights that Tuscany is renowned for. Relish the tangy pecorino cheese, handmade pasta pici, fruity olive oils, and sip the Tuscan wines Brunello and Nobile.
It’s not just a bike tour: it’s an immersion into Tuscany’s culture, history, and tantalizing flavors.




Pienza – the perfect town

Meet & Greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets. Optional test ride to San Quirico d’Orcia 20km /12,5 miles


Montepulciano & Vino Nobile

Your tour starts with a circular ride from Pienza.

Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you’ll come to Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.

Distance: 53,5 km / 33 miles
+ 1068 m / – 1070 m


Montalcino Brunello Land

Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe.
You can have lunch in Castiglione d’Orcia, then push on to the monastery of Sant’Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you’ve just biked, then reward yourself with a wine tasting at internal Enoteca. Have a dinner following our suggestions.

Distance: 44,4 km / 28 miles
+ 920 m / -876 m


Siena & Monte Oliveto Maggiore Abbey

Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons.
Following a picturesque crest road, you’ll ride by Monte Oliveto Maggiore Abbey , a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. Afterwards, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands.
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.

Distance: 56,7 km / 35,5 miles
+1035 m / -1217 m


Chianti Hills

Ride from Siena to Castellina in Chianti, following the “chiantigiana” road.
Along the way you can 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. There’s also the chance to shop at a first-class ceramics workshop just before Radda in Chianti. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get in Castellina Castellina’s medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants.

Distance: 55,6 km / 34,5 miles
+ 1019 m / -787 m


Greve in Chianti & Panzano

Circular bike ride to Florentine 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 . Have a stop at Greve’s main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate and the keep of the medieval castle. relax by the vanishing edge pool spilling into the countryside of endless vineyards

Distance: 55 km / 34 miles
+1019 m / -1019 m



Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town


Extra stage on request: Castellina 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.
Pretty 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. Also seen in the distance are the seventeen towers of San Gimignano. 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!

Distance: 58 km
difficulty: challenging

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Tour start in Pienza
Tour end in Castellina

classic tuscany bike tour map



best period : from March to end October

DIFFICULTY : medium to challenge

TOTAL DISTANCE : 280 km / 177 miles in 5 stages



Tour Reviews

5.00 based on 2 reviews
13 February 2016

Thanks very much guys for a great trip. We really appreciated the extra touches you add to the Tour and tried most of your recommended Restaurants which were excellent. The countryside was beautiful and the wine….well …say no more

13 February 2016

We had an absolutely great time! Castellena de Chianti and Pienza were our two favorite areas to bike in and I am so glad we chose Cicloposse

Leave a Review


Cost: € 1490 per person in double occupancy
Single room supplement € 590


Six nights in excellent four & three-star superior hotels
Six breakfasts
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 Castellina
Keepsake Cicloposse water bottle
Sales taxes

Not Included

Bike Rental per entire tour
Hybrid bike euro 180
Race bike, E-Bike, Gravel Bike         euro 240

City Tax  each village charges a tax per day between euro 0,70 to euro 4,00

Cooking lesson & Wine tasting

il Chiostro – 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.

La Bandita Townhouse – Pienza

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

Hotel Giglio – Montalcino

A charming retreat in the heart of town, hotel Giglio, family-run, in a warm and quiet building, facing a gorgeous landscape, the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below. Plus a great restaurant where enjoy gourmet tuscan dinner

Vecchia Oliviera – Montalcino

Vecchia Oliviera is located in the historic center of the city of Brunello and stands next to Porta Cerbaia, one of the six ancient gates to the city of Montalcino. an old oil mill restored and transformed into this charming hotel with garden overlooking Orcia valley

Villa di STR – Siena

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

Palazzo Squarcialupi – Castellina in Chianti

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

Hotel Salivolpi- Castellina in Chianti

Salivolpi is an old country house recently converted into a hotel whilst keeping its original architectural features. It is located on the hills on the site of the former Etruscan Castellina, surrounded by vineyards, olive groves and cypress trees, it has a wonderful panorama stretching over the Elsa valley

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