Tuscany hilltown the best of

We put together this short bike tour- 3 full days of cycling and 2 half days – for those who do not feel like taking a vacation entirely on a saddle, besides each day there will be a choice for easier and short bike rides and more challenging ones.

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.


  • 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 soupe, Panzanella tuscan Salad, fresh pastasas pici  and delicious pastries of Siena
  • Enjoy gracious hotels with distinct regional and charming style.



1 – Welcome! 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

2 – Montepulciano & Vino Nobile
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.
Option A : Moderate to challenging Distance: 55 km/ 34 miles
Option B: easy to moderate distance 35 km /21 miles

3 – Montalcino Brunello land
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.
Option A :Moderate to challenging Distance: 46 km/28, 5 miles
Option B: Easy to Moderate distance 34 km / 21 miles

4 – Siena, Etruscan and Palio race
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.
Option A: Moderate to strenuous Distance: 58 km/36 miles
Option B: Moderate distance 50 km /32 miles

End of bike tour after breakfast


Price & Inclusions

Cost: Euro 990 per person in double occupancy

Single room supplement euro 250


Four nights in excellent three-star superior hotels

Four breakfasts

Route notes, maps, elevation gain and city map

Sightseeing, restaurant and shopping suggestions in handbook

All Baggage transfers

Pick-up of bikes and gear in Siena

Sales taxes

Not Included
Bike Rental per entire tour

Hybrid bike  euro 105

Race bike  euro 120

E-Bike  euro 120

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


Renting GPS for 4 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!



Self Guided




From March to October