Tuscany Biking | Pedaling on Wine Country | Self guided

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Cycling in Tuscany on Exclusive Italy Self Guided Bike Tour

Starting from Pienza, which dominate the Val d’Orcia you will cross  Siena, ending in Castellina, the hearth of Chianti wine area.

Yes, there are hills to climb, but your efforts will be well rewarded with a sunny Mediterranean ambiance and a spirited flair for hospitality, Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.

Route we selected takes you along tranquil country lanes tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys, and medieval forts. Staying in Pienza, Montalcino, Siena and heart of Chianti, you are sure to experience the true essence of Tuscany, where history and beauty fill the heart as water fills a well.

Strongly suggested, after spinning through rolling vineyards, golden wheat fields and chalky white hills by day, savor pecorino cheese, homemade pasta pici, fruity olive oils and sip Tuscan wines Brunello and Nobile.

Tour Details
Tour name Tuscany Cycling on Wine Country
Type of tour Self guided, cycling
Duration 6 nights, 7 days
Departures From March to October, you can start any day of the week
Level Moderate to Challenge
Total Distance 297km / 184mi
Daily mileage 43 to 58km / 29 to 36mi
Start Pienza
End Castellina in Chianti
Suggested Airports In / Out: Roma or Florence


  • 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
  • In ancient cellars, taste superb Tuscan wines, from Vino Nobile di Montepulciano to Brunello di Montalcino
Not Included
Optional Services
  • Six nights in excellent four & three-star superior hotels
  • Six breakfasts
  • Bike Delivery to Pienza and professional bike fitting
  • Route notes and maps with elevation gain, city maps
  • Sightseeing, restaurant and shopping suggestions
  • All Baggage transfers
  • Drop Off bikes and gear in Castellina
  • Keepsake “BTS” water bottle
  • Sales tax
  • City Tax; each village charge a tax per each day between euro 0,70 to 2,50
  • Bike Rental
  • Pre/Post Additional Nights
  • Transfers to/from other destinations on the Island
  • Cooking lessons
  • Cheese tasting
  • Wine tasting
  • Room upgrade options

Day 1Benvenuti to Pienza - the perfect town. Opt. ride to San Quirico 20km / 12mi

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.
Meals included: welcome aperitif

Day 2 Pienza loop to Montepulciano & Vino Nobile. 55km / 34mi, rolling hills

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.
Meals included: Breakfast

Day 3Pienza to Montalcino & Brunello Wine. 46 km / 28 mi, rolling hills and hilly

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 dinner at our favourite wine cellar.
Meals included: Breakfast

Day 4 Montalcino to Siena & Monte Oliveto Abbey. 58km / 36mi, rolling hills

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.
Meals included: Breakfast

Day 5Siena to Castellina & Chianti Hills. 50km / 31mi, rolling hills to hilly

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.
Meals included: Breakfast

Day 6Castellina loop to Greve in Chianti & Panzano. 56km / 35mi, hilly

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
Meals included: Breakfast

Day 7Arrivederci! Or Monteriggioni loop. 32km / 20mi

The short bike ride allow you to visit 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. Back to Castellina where you will leave bikes.
Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town
Meals included: Breakfast

Extra DayCastellina to San Gimignano. 58km / 35mi hilly

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. 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!


Self Guided
Tour Price: 1390€

Price based on double accommodation, it can change according to the period.

Make it custom: contact us for a quote!

Single occupancy: 450 €
Solo traveler: ask for a quote

Private & Custom departures at any time

Bike Rental: (price/week)
Touring/Hybrid Bike € 180
Race Bike  € 210
E-bike € 210
Tandem € 350
Road bike for rental


Carbon frames with Ultegra 11 speed; compact groupset. 

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Electric bike for rental


The hills won’t be so hard with our new Scott and Vektor E-Bikes.

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Touring Hybrid bike for rental


Hybrid bikes blend the characteristics of race and mountain bikes.

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Standard version
Il-Chiostro bike hotel Pienza
Day 1 & 2  – Il Chiostro Relais, 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.

Giglio hotel Montalcino
Day 3 – Giglio Hotel, 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

Chiostro del Carmine Siena bike hotel
Day 4 – Il Chiostro del Carmine, Siena

Il Chiostro del Carmine has been meticulously restored from a XIV century Carmelite Monastry, place of history and holiness, remained intact in the centuries, with its delightful and quiet courtyard. It is situated a few hundred metres from the Siena Cathedral and from Piazza del Campo

squarcialupi Castellina Bike Hotel
Day 5 & 6 – Palazzo Squarcialupi Hotel, 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

Upgraded version
BANDITA Pienza bike hotel
Day 1 & 2 – La Bandita Townhouse, Pienza

La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza.

Day 3 – Si Montalcino

Hotel SI Montalcino is small charming hotel completely renovated, located on the panoramic road to S.Angelo in Colle, one km away from the walls of Montalcino.

Chiostro del Carmine bike hotel siena
Day 4 – Il Chiostro del Carmine, Siena

It is situated a few hundred metres from the Siena Cathedral and from Piazza del Campo.

Salivolpi Hotel Castellina by bike
Day 5 & 6 – Salivolpi Hotel, Castellina in Chianti

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.


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

Kevin & Kevin, New Zeland
November 1st , 2019