Authentic bike tour Italy

This Tuscany’s combination of natural beauty, medieval and renaissance art, architecture and friendly people will enchant you: Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.
Cycling through unparalleled countryside by day complements incredible Tuscan cucina by night. This gastronomic paradise beckons to lovers of sublime provincial cooking and superb wine; fresh pastas, porcini mushrooms, and locally produced pecorino cheese from Pienza  mark the region’s celebrated dishes, which just happen to be the perfect match for its world-class wines.
Every day will bring new experiences enriching you.


  • Explore some of the region’s most celebrated towns, including Pienza, Montalcino, Siena and San Gimignano
  • Sample fine wines before dining on local specialties
  • Castelli road: the Chianti castles route: the surprising number of castles, fortified farm houses, towers and fortified Abbeys in the area
  • A visit to the famous Castello di Brolio before Gaiole is a must!

Welcome to Pienza

We'll meet you in Pienza, the purest Renaissance town in the world. Please note that the closest station to Pienza is Chiusi—35 km from Pienza--on the Rome-Florence train line. After checking-in at your pre-arranged location in a former 15th century convent, itself is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II.
Pienza is one of the four UNESCO World Heritage Sites you’ll encounter during your week-long history-laden cycling trip.
After bike fitting optional bike ride to San Quirico d'Orcia 20km /12,5 miles

Montepulciano & Vino Nobile

Loop ride Montepulciano & Montichiello
You’ll follow a route that winds through a scenic landscape chequered with vineyards, cypresses, and medieval village. Stop Monastery where part of “English Patient” was filmed. Among the sites you’ll ride through is the hilltop hamlet of Castelmuzio and Montepulciano, another hilltop village that will make a perfect lunch/wine stop. Montepulciano is home to the famous Vino Nobile and full of renaissance palaces. After your relax head back to Pienza through Monticchiello, the quintessential Tuscan hill town.
Total Distance: 55 km/34 miles

Montalcino Brunello town

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.
Total Distance: 46 km/28,5 miles

Murlo etruscan way to Siena

Ride from Montalcino to Siena, your detailed directions will take you through typical postcard Tuscan scenery, Italy’s most photographed region—for good reason Start with 10 km descent and pass through Buonconvento, Heading northbound to Siena, we are treated to more gorgeous cycling along secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum, which is worth the visit. Continue to Ville di Corsano always on a breathtaking scenery up to Siena arch gate Porta San Marco. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You'll have time to take a leisurely stroll about this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo.
Piazza del Campo is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.
Total Distance 52 km/32,5 miles

San Gimignano 'Città delle Torri'

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.
You will be soon in quiet road through Santa Colomba and Celsa pass the medieval hamlet “Fungaia” known to the sienese chronicle since 1247, it is on the old medieval pilgrim trail Via Francigena. Stop in Casole d’elsa: originally inhabited by the Etruscans that means before roman empire. The fortress and the defensive walls are still visible today, although the town gates have unfortunately been destroyed during the Second World War. Continue to Castel San Gimignano pedaling a a very minor scenery road. Also seen in the distance are the seventeen towers of San Gimignano, just after San donato village. 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: 70 km/43,5 miles

Castellina in Chianti

The previous days have prepped our legs for the famed hills of Chianti, which await us today! The first stretch crosses an almost impossibly scenic clutch of hills blanketed with vineyards and thick forests. It's breathtaking, and so is the ride! Hill climbing with many recovery sites on your way including medieval Barberino and Tavernelle the gateway town to the Chianti Classico wine-producing region!
Back in the saddle, we continue along the same winding panoramic road to Castellina in Chianti. The town occupies a kind of panoramic balcony over Chianti, positioned on a high hill at the centre of three valleys. It is one of the most important centres of inhabitation in the Chianti.
Total Distance: 40 km/25 miles or longer option 60 km /37,5 miles

Radda in Chianti

Optional bike trip to Via dei Castelli road and stop for a capuccino in Radda in Chianti. Distance 35Km / 21,5Miles. ARRIVEDERCI
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 dinners.
Chiostro 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
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.
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
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 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.

Terre di Siena Beautiful Landscape

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Bike tour Tuscany landscape
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cycling trip val d'Orcia
Italy bike tour wine country
Siena by bike main square
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tuscany tour pienza cheese tasting

Price & Inclusions

Cost: Euro 1450 per person in double occupancy
Single room supplement euro 380

Six nights in excellent three-star superior hotels
Six breakfasts
Route notes and itineraries & sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in Castellina
Keepsake Cicloposse water bottle
All tax and service charges

Not Included
Bike Rental per entire tour
Hybrid bike euro 180
Race bike     euro 210
E-Bike         euro 210

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

Cooking lesson & Wine tasting
Renting GPS for 6 days – 50 euro
We can rent you a Garmin Edge Touring. It works like the GPS navigator you use in your car, only with maps and features specifically designed to help you find your way by bike. We will upload all the route notes and you will have really no problems in finding your way to the next town!




Tour Reviews

18 ottobre 2016

Hi Giuliana! Thanks so much for the pictures – we had been meaning to write to you! We had such a wonderful time in Italy. The bike trip was one of our favourite highlights … we told everybody about it. Both Sarah and I had such a blast. We really can’t wait to do it again! I’ve attached a few pictures we took, hope you enjoy. Thanks again … all the best.

18 ottobre 2016

We want to thank you for such a great vacation. The biking was the highlight of our stay in Italy. We were able to see such untouched beautiful areas that we just couldn’t have seen otherwise. And, the towns we visited were generally much less touristy than where most people go. Even San Gimignano emptied of the tourists by late afternoon and we were able to wander through this beautiful town in peace. Also, all of the hotels were wonderful and your suggestions of restaurants were all fantastic

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