Bike Adventure Italy, the best of Tuscany by bike

Senza titolo 2 Southern Tuscany Bike Trip


Cypress roads, small villages on top of hill, hot springs, abbey immersed in park, group of cypress, this self-guided tour covers this small but stunning part of Tuscany!
Discover the beauty of Montepulciano, Pienza, Val d’Orcia, Montalcino and its famous Brunello wine, and Siena, as well as many little medieval villages on your ride every day. This is a relaxed tour with three-night stays in 2 different hill towns, so you are not always packing. If you wish to take a day off  from riding you can sightsee, have a wine tasting, and walk along beautiful paths.
Food and wine are highlights of this trip,  we suggest local trattorie where you’ll taste the local homemade pasta pici, the local cheese pecorino, as well as typical appetizers bruschetta and crostini, while sipping great wine!

Pure Biking Highlights

A quintessential Tuscan experience from South to North
Sample fine wines before dining on local specialties
Scenic cycling through the stunning landscape of the Val d’Orcia


Pienza 'the perfect town'

Arrival at Chiusi Chianciano train station in the morning/ early afternoon and transfer on your own to the first hotel il chiostro in Pienza, your home for the next three nights. The “perfect town” almost entirely built between 1459 and 1462, Pienza 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 about its cobblestone streets. Gift hunters will also be enthralled, and Pienza is a veritable gastronomic paradise.
Meet and Greet, we'll fit your bikes and introduce you to each day ride. First loop to San Quirico to test the bicycle and the equipment! Stop in the village at Horti e leonini Garden, the top attraction of town.
Total Distance 22 km/13,7miles

Medieval City Center & Vino Nobile di Montepulciano

Loop ride to Montepulciano and Monticchiello. Start your day with a pleasant downhill, You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages…This is where “the English Patient” was filmed. Among the sites you’ll ride through there are the hilltop villages of Castelmuzio and Petroio.
Today’s ride will take you to Montepulciano, which is famous for the production of Vino Nobile di Montepulciano. After a stroll about the medieval streets of this village, you can stop to visit one of the typical wine cellars in town, the oldest one which is situated under the Ricci Palace.
Back to Pienza through Monticchiello… another hilltop village!
Total Distance 55 km/34,3 miles

San Giovanni d'Asso & Truffles

Loop ride to Trequanda, Montisi, San Giovanni d’Asso
Enjoy the 2 miles downhill and cycle up and down about 10 miles and you will visit the mediaeval village of Trequanda, one of the most unspoilt areas of the province of Siena. It developed around a 13th century castle of which a cylindrical tower with battlements still remains today. Stop at the ancient borgo of Montisi, which is a natural bridge between the "Crete Senesi" and the Val d’Orcia. And now enjoy km downhill and get to San Giovanni d’Asso, famous worldwide for valuable white truffle; the area is rich with farms, hamlets and castles, which reminds you of the colors of the paintings of the Renaissance. Back to Pienza through little districts. Total distance 55 km/34,3 miles

Montalcino & Brunello Wine

Bike ride to Montalcino Today’s ride will take you to Bagno Vignoni, a thermal spa town that dates back to Roman times right before reaching the beautiful Castiglione d'Orcia, with the imposing Rocca A tentennano. Enjoy a long downhill to the monastery of Sant'Antimo, 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, where you will stay for next three days, you’ll pedal through magnificent vineyards. It is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italy's premier fine red wines, Brunello di Montalcino. Total distance 48 km/30 miles

Monte Oliveto Abbey & Le Crete

Loop Ride to Monte Oliveto 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 50 km/31,2 miles

Castles & Wineries

Loop Ride to Poggio alle Mura Castle
Today you’ll take a beautiful ride to Maremma side of Montalcino; on your way you can stop at a miniscule village called Sant’Angelo and then enjoy the downhill to Poggio alle Mura where you can visit the medieval castle towering above mountainous forests, lush and rolling vineyards. The origin of the fortress can be traced to the ancient Etruscans, but its deepest historical niche was carved during the Middle Ages. The castle's historical name is Poggio alle Mura, which is today called also Castello Banfi and it is the crown of a 7,100 acre viti-vinicultural estate and for visitors there are interesting glass and wine museum, Enoteca wine bar and Taverna. Back to Montalcino through vineyards, it is also possible to stop in other small brunello wineries. Total Distance 40 km/ 25 miles


Bike ride from Montalcino to Siena via Murlo
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

Chianti hills

End of tour after Breakfast- optional bike ride in chianti to Castello di Brolio. distance 50 km/31 miles
bagno vignoni bike trips
active wine tour
bike tour in tuscany
bike tours italy
cycling vacation Tuscany
cycling in Tuscany
luxury bicyling vacation
pure adventure tuscany
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.
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
luxury upgrade in Pienza: La 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
Luxury upgrade in Montalcino: Castello di Velona
Soak up superb hilltop views at this elegant medieval fortress featuring a magnificent vantage point above the Val d'Orcia, a Tuscan restaurant and a free spa center. Standing above the old Via Clodia, which connected southern Etruria to Rome, Velona Castle was built as a medieval fortress in the 11th century.
Luxury upgrade in Siena: Relais Campo Regio
More of a boutique guest house than traditional hotel, Campo Regio Relais’ 6 rooms are centrally positioned in the heart of Siena’s historic centre, allowing guests to easily reach the most important monuments of the city; the main square, Piazza del Campo, the Duomo, and the museums that house the masterpieces of Sienese art.

Amazing Southern Tuscany

Price & Inclusions 

Cost: Euro 1350 per person in double occupancy
Single room supplement Euro 380
Solo Traveller Supplement Euro 450
Luxury version: Bandita, Velona and Campo Regio lodgings, price on request

Seven nights in excellent four & three-star superior hotels
Seven breakfasts
Route notes and itineraries & sightseeing, restaurant and shopping suggestions
All Baggage transfers
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 210

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

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

Giuliana and Marco- Thank you very much for putting together such a wonderful tour for our group (Ken Gellerman’s trip) in Tuscany. My wife, Jan, and I had a great time. I loved the hills (both going up as well as coming down), and finishing each day in the hill towns was really fun. The hotels were great, the bikes were awesome, the food was great, the wine was great. What more can I say? We are looking forward to our next cycling trip in Italy.

18 Ottobre 2016

It was a wonderful trip, bikes were in great condition, and your advice about the hills was very sound…respectable hills demanded a careful pace for an out-of-practice cyclist. Geoffrey, on the other hand, took to the hills like a pro. Thankfully, we went without any flats…so you will find your spares and your patch kit untouched. We will be sure to suggest Cycloposse to our friends…We thoroughly enjoyed our time here. Your country is beautiful…I will hope that in my next life, I will be Italian…e my next life

Leave a Review