Tuscany Cycling | Hill-top Towns for Wine Lovers | Short Break | Self guided

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A Unique Tuscany Cycling Tour Experience in the hearth of Tuscany: from Pienza in Val d’Orcia you will taste the flavour of Brunello di Montalcino, arriving to Siena and climbing the Chianti Hills.

This cycling holidays is a mixture between moderate and challenging ride, but where you can decide which way you want to ride in the morning.

3 days and half of cycling will complete your cycling holidays in Italy or you can decide to add other days in another region of Italy for another brief bike trip or longer.

Whether crowned by timeless villages, covered by vineyards and olive groves or strewn with wildflowers, the hills of Tuscany have one thing in common: they’re perfect for exploring on two wheels.  

Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.

Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Brunello wine land, savour meals created from the finest local ingredients and relax in charming Tuscan retreats.

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Tour Details
Tour name Tuscany – Hill-top Towns
Type of tour Self guided, short break Cycling
Duration 4 nights, 5 days
Period  All year round, you can start any day of the week
Level Moderate or Challenging (2 option each day)
Total Distance

152km / 95 miles

Daily mileage

44 to 58km / 28 to 36 miles

Start Pienza
End Siena
Train Stations In: Chiusi / Out: Siena
Suggested Airports In / Out: Rome or Florence


  • Scenic cycling through the stunning landscape of the Val d’Orcia
  • Taste the splendid wines Brunello of Montalcino, Vino Nobile di Montepulciano
  • Delight in hearty Ribollita soup, Panzanella Tuscan Salad, fresh pastas as pici and delicious pastries of Siena
  • Enjoy gracious hotels with distinct regional and charming style.
Not Included
Optional Services
  • Four nights in excellent four & three-star superior hotels
  • Four 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 Siena
  • 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
  • Wine tasting
  • Room upgrade options

Day 1Welcome! Benvenuti in Toscana

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. Gift hunters will also be enthralled. Pienza is also 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 Leonini Garden, the top attraction of town. Total Distance 22 km.
Your charming Hotel Il Chiostro is housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza. Entirely rebuilt between 1459 and 1462, itself is a rare masterpiece: it was the brainstorm of Pope Pius II

Day 2 Pienza Loop to Montepulciano. 35 or 55 km / 21 or 34mi

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…Among the sites you’ll ride through meet 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. Visit one of the typical wine cellars in town, the oldest one in town is situated under the Ricci Palace. Back to Pienza through Monticchiello… another hilltop village.
Meals included: Breakfast

Day 3Pienza to Montalcino & Brunello Wine. 34 or 46km / 21 or 29 mi

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. Enjoy a long downhill to the monastery of Sant’Antimo where you might catch one of several vesper services performed each day by the monks.. On your way to the Etruscan village and wine town of Montalcino, where you will stay , you’ll pedal through magnificent vineyards.
Montalcino 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 Italian’s premier fine red wines, Brunello di Montalcino.
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 & Palio race. 50 or 58km / 32 or 36mi

Ride from Montalcino to Siena. On the way you’ll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands.
Easier: Start with 10 km descent and pass through Buonconvento. Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum. Continue to Ville di Corsano always on a breathtaking scenery and end up in Siena arch gate Porta San Marco. You’ll have time to take a leisurely stroll around 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.
Meals included: Breakfast

Day 5Arrivederci! Good bye!

After breakfast end of the tour.
Meals included: Breakfast


Self Guided
Tour Price: 1090€

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

Single occupancy: 300 €

Private & Custom departures at any time

Bike Rental:
Touring/Hybrid Bike € 105
Race Bike  € 120
E-bike € 130
Tandem € 280
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 – 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.

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. 

Chiostro del Carmine bike hotel siena
Day 4 – 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.

Luxury version: quote under request
BANDITA Pienza bike hotel
Day 1 & 2 – La Bandita Townhouse, 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

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. 

Campo regio siena-cycling
Day 4 – Campo Regio Relais, Siena

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