Tuscany Classic: Siena and beyond

This self-guided bike tour covers a stunning part of Italy: Tuscany, Siena’s surroundings and the hills of Chianti.
Ride through medieval villages such as Montepulciano and Montalcino, both famous for their exquisite wines that of course you can enjoy during a wine tour. Cycle up and down the hills of Chianti. Visit Siena and enjoy its medieval character. Siena is one of the best preserved medieval towns in Italy and a UNESCO World Heritage Site. If you travel during the summer you might even have the chance to see the Palio, a horse race inspired from the medieval tradition which takes place in the center of Siena.
This is a relaxing tour with 2-night stays in 3 different towns, allowing you time for exploring. If you wish to take a day off from riding you can go sightseeing, walk the Tuscan countryside, do some wine tasting and enjoy the local food. Tuscany has everything you desire for a perfect vacation!

Price from : 1750€
Region : Tuscany
Duration : 7 Days / 6 Nights
Level :
Type : On the way
Category : Bike
Trip : Self-guided
Activity : Hybrid
Dates : Starts any day

Click below to see hotels versions.

Day 1 :   Arrive in Tuscany

Distance 1 : 14 Miles - 22 Km 

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 two 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. If you arrive early enough, the first loop is to San Quirico to test the bicycle and the equipment! Stop in the village at Horti e leonini Garden, the top attraction of town.

Day 2 :   Wine tour in Montepulciano

Distance 1 : 32 Miles - 52 Km 
Elevation gain 1 : 1058 Meters 

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!

Day 3 :   Visit Montalcino and the Brunello vineyards

Distance 1 : 27 Miles - 44 Km 
Elevation gain 1 : 856 Meters 

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.

Day 4 :   Loop tour of Tuscany

Distance 1 : 29 Miles - 46 Km 
Elevation gain 1 : 695 Meters 

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. Back via San Giovanni d’Asso, the truffle village in Tuscany.

Day 5 :   Cycle to Siena

Distance 1 : 34 Miles - 55 Km 
Elevation gain 1 : 857 Meters 

Start with 10 km descent and pass through Buonconvento, Heading northbound to Siena, where more gorgeous cycling on secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum, one of the highlight of the day.

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.

Day 6 :   Ride the Chianti hills

Distance 1 : 34 Miles - 55 Km 
Elevation gain 1 : 936 Meters 

Loop Ride around Siena in Chianti. Along the way you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. Not far away is Castello di Brolio, a castle that you can visit.Back to Siena via chiantigiana road.

Day 7 :   Leave Siena

According to your program, we can arrange accommodations and transportation.

Average / Day : Distance : 45.67 Km / 28.33 Miles - Elevation gain : 880.40 Meters

Click below to see hotels versions.

Day : 1, 2

Relais Chiostro di Pienza is situated in the heart of Pienza, a Renaissance city planned by Rossellino - following the will of Pope Pio II, Enea Silvio Piccolimini. This ancient convent of the fifteenth century overviewing the Orcia Valley offers functional and confortable rooms, thanks to its particular structure. The hotel guaranties comfort and enjoyment.

Day : 3, 4

A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, facing a gorgeous landscape over the Tuscan countryside. This is Il Giglio.Frommer's Guide Tuscany & Umbria 4th edition 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.Lonely Planet Guide TuscanyThis place, with comfortable rooms, is probably the pick of the crop

Day : 5, 6

The Villa of Str, Located just outside the old city walls of Siena, The Villa is a charming liberty style residence dating from the early years of the twentieth century and within easy walking distance from the historic centre of Siena. Offering solutions for all needs, whether as a family, a couple, with friends or even with your pets, all our rooms are tastefully decorated with respect for the aesthetic and historical origins of the building. Whatever your reasons for visiting Siena, our hotel will prove welcoming, stylish and comfortable, a great base from which to explore the medieval town of Siena.

Bikes available for your tour

The characteristics of this bike are presented as an example and are not guaranteed
Please note that any bike changes during the trip may incur an extra fee.

Hybrid bike - Standard
FLAT BAR - ( or equivalent)

we put together the disc brake for the stability and the reliability of braking and the compact gear with 42 teeth in the back, an advanced gearing concept that helps maintain rider efficiency.

About disc brake we have the advantage of the power – it generate an incredible amount of stopping power, usually far more than is necessary to adequately stop a road bicycle and Reliable, all weather braking.
For the rest is an hybrid with straight handlebars, lightweight with hybrid wheels ad narrow tires for low rolling resistance allowing for greater speed and less exertion when riding on paved road.

  • Frame: Aluminum frame Fork: Full carbon Chain ring: Shimano Deore XT 38/28 - compact
  • Cassette: Shimano Deore XT 11/42 - 11 speed Brakes: Shimano Deore XT Saddle: Selle Italia
  • Wheel set: Shimano VH-RX010 Weight: 10 kg
  • Size: S, M, L

• 1 new bottle

• Helmet

• Odometer

• Lock

• Pump frame


1 Handlebar bag with rain cover containing : Tire levers / 2 Spare tubes / Toolkit


• Pedals are included, flat by default or toe straps on request. If you want to use your bike shoes, you should bring your own pedals + pedal wrench : we will be happy to install them on your bike.



Roadbook for Discovery allows you to travel freely with all the information you need for your trip: Stages, points of interest, itineraries with interactive guidance, travel documents.

All in offline mode, you download your file before leaving, then you have all the information necessary for your trip. (Phone not provided).


Our roadbooks are complete packages of information that will help you to guide yourself through the itinerary that we have planned and laid out. We have invested significant time and incorporated the feedback of our customers over many years (since 1997!) to make our roadbooks even better. Our roadbooks include: color maps, highlighted routes, touristic information, orientation points to reach hotels, and easy to follow step by step directions (cue-sheets). Please note that for custom itineraries you will not have cue sheets. Only maps and GPS routes.


Our Travelbooks are complete packages of information that will help you to guide yourself through the itinerary that we have planned and laid out. You will find information about the hotels, itinerary, regional informations...

Daily Elevation Profiles
Average / Day : Distance : 45.67 Km / 28.33 Miles - Elevation gain : 880.40 Meters
Day 2 :   Wine tour in Montepulciano

Option 1: 32 Miles - 52 Km  Elevation gain 1 : 1058 Meters 

Day 3 :   Visit Montalcino and the Brunello vineyards

Option 1: 27 Miles - 44 Km  Elevation gain 1 : 856 Meters 

Day 4 :   Loop tour of Tuscany

Option 1: 29 Miles - 46 Km  Elevation gain 1 : 695 Meters 

Day 5 :   Cycle to Siena

Option 1: 34 Miles - 55 Km  Elevation gain 1 : 857 Meters 

Day 6 :   Ride the Chianti hills

Option 1: 34 Miles - 55 Km  Elevation gain 1 : 936 Meters 


  • 6 nights of accomodation in superior hotels of charm with private shower and/or bath
  • Daily breakfast at each hotel, 1 dinner included
  • Orientation in person with our local guide
  • Hybrid bike rental included
  • Detailed ROAD BOOK, including details maps, touristic information, step by step itinerary and cue sheets
  • Guidance Applicaton (phone not provided)
  • All luggage transfers
  • Comprehensive trip literature
  • Technical and emergency support available at all times

What's not included

  • Airfare to and from the trip
  • Lodging before and after the trip
  • Drinks
  • Some meals are not included in each destination, which gives you the opportunity to explore regional cuisine on your own. You will find all information needed with our team support in your roadbook.
  • You have to pay local taxes each day (0.70 to 2.50 eur) in cash to each hotel (tourist administration tax)

Informations & Recommendations

To get to the start of your Tour (Pienza), the easiest airport are Rome Fiumicino and Florence Peretola :

  • Fiumicino aiport (Roma) take the train “Leonardo Express” to Roma train station (About30 minutes, start each half hour and is direct). From Roma to Chiusi you willfind many trains (about 2h). Then take a taxi to your hotel in Pienza (about 60eur).
  • From Florence Peretola (Florence) take a bus or a cab to Florence train station. Then Take a train from Florence train station to Chiusi (about 1h45). To reach Pienza, take a taxi to your hotel (about60eur).
  • Your Tour ends in Siena. The train station is very close to Siena. You will find direct trains to Roma (3h) and Florence (1h45)

Tour rates

Contact our tour consultants for more information and an exact rate based upon your travel dates.

Price from* & per person Double occupancy Single supplement
(traveling with a group)
Standard 1750 € 400 €
*Rates vary according to hotel availability and specific start date. Please contact us for triple room rates

This tour is not suitable for children


Guidance Application Included
Biking Roadbook Included
Travelbook Included

Bikes available

Bikes available Options per person
Road Bike Rental
    Standard 120 €
Electric assist bike
    Standard 160 €
Gravel Bike Rental
    Standard 150 €

Please note that any bike changes during the trip may incur an extra fee.

Services available

Services available
Cancelation insurance 6%

Bot scann is mandatory