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!
BIKE INCLUDED
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.
Accommodation : Relais Il Chiostro di Pienza - "Pienza"
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!
Accommodation : Relais Il Chiostro di Pienza - "Pienza"
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.
Accommodation : Hotel Il Giglio - "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.
Accommodation : Hotel Il Giglio - "Montalcino"
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.
Accommodation : La Villa Di STR - "Siena"
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.
Accommodation : La Villa Di STR - "Siena"
Day 7 : Leave Siena
According to your program, we can arrange accommodations and transportation.
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 |
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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.
• 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.
Hybrid bike - Standard
FLAT BAR - ( or equivalent) INCLUDED 
With drop handlebars, these bicycles are built for traveling at higher speeds on paved roads, sometimes referred to as racing bikes. Our race bikes are all brand-new, reliable, and well maintained for your ideal cycling experience of Italy. Extremely efficient, incredibly smooth to ride and will take you everywhere with stability after a professional bike fitting session. Race bike with drop handle bar is strongly suggested if you use regularly those bike!
Road bike - Standard
FULL CARBON FIBER - ( or equivalent) with supplement (120€) 
Electric bikes are regular pedal bikes that provide electric assistance whenever you want.
Electric assist bike - Standard
E-BIKE SCOTT E-SUB CROSS 10 - ( or equivalent) with supplement (160€) 
New Scott Addict Gravel 20 with drop handle bar, a cyclocross touring oriented , disc brake and wider tires to enjoy the classic strade bianche in Tuscany: Eroica itinerary and Francigena path. Our gravel bikes are all brand-new, reliable, and well maintained for your ideal cycling light off-road experience of Tuscany. Lightweight because of carbon fiber frame, hydraulic disc- brake,these bikes can perform on both the road and off the road.
Gravel bike - Standard
BIKE SCOTT ADDICT 20 - ( or equivalent) with supplement (150€) |
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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. |
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Hybrid bike - Standard
FLAT BAR - ( or equivalent)
INCLUDED
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.
Accessories
INCLUDED
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).
INCLUDED
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.
INCLUDED
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...
Option 1: 32 Miles - 52 Km Elevation gain 1 : 1058 Meters
Option 1: 27 Miles - 44 Km Elevation gain 1 : 856 Meters
Option 1: 29 Miles - 46 Km Elevation gain 1 : 695 Meters
Option 1: 34 Miles - 55 Km Elevation gain 1 : 857 Meters
Option 1: 34 Miles - 55 Km Elevation gain 1 : 936 Meters
Included
- 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 € |
This tour is not suitable for children
Accessories
| Accessories | |
| 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% |
United States
Overall the trip was awesome! Since we have done two trips (Loire Valley & Tuscany) with you, we had fun processing the comparisons. Here's our quick feedback: 1. Cycling: Tuscany was so hard! Ken & I are very experienced cyclists, and those hills were tough! However, the views and venues in Tuscany were spectacular! (The downhills were fun too!) From a vacation perspective, France was easy because it was flat.... 2. Hotels: No contest- Italy was 10 times better. Best Hotel was Il Giglio in Montalchino. All the hotels were great. 3. Food- France gets the nod here. While we all love great Italian Food, we get that here in the US. The French food was off the charts spectacular.... special. 4. Wine- again France gets the better rating. 5. Road Safety- France was safer. Italian drivers are crazy!!! :) 6. Site seeing- France gets the nod. Lots of Castles and Vineyards. We didn't really see many places to stop and site see in the same way we did in France. We love the Abbey and many of the Italian Catholic Churches, France just had more... Overall we are very happy with the trip, and for the record, my buddy Ken needs to train harder to keep up with me! :) Thanks for all your work on this trip.
United States
Our cycling trip was truly amazing. It was our fifth cycling experience and I can honestly confirm that the beauty of Tuscany is unbeaten. We absolutely loved the beauty of the little medieval villages around Montepulciano, Pienza, Montalcino and Greve. We feasted on melon and prosciutto, caprese salad, all sorts of pasta dishes, wild boar , pecorino cheese , massive Florentine steaks , truffles, Prosecco and of course a variety of wines. The Brunello wine was our absolute favourite and I already long for a glass ! It was overall a fantastic trip, thank you.
United States
The trip was awesome! Great views, really good rides thanks to the e-bikes, and also amazing food! Thanks for planning the trip!
United States
It was a great trip! The E-bikes worked out great for the kids, they had sore buts at the end but we were all able to ride at paces that were comfortable for us. Some of the roads had more traffic than felt safe, particularly since Italy does not do shoulders. Having said that, I loved the routes and scenery and the distance/climbing made for a good daily challenge but wasn’t too much. The local bike company was great and very helpful and supportive. The bikes were high quality and the Garmin head-unit made navigation easy. Pienza was my favorite town and the Hotel Costenago (sp?) was our favorite hotel. The only feedback there is that the hot tubs unfortunately were not hot, more like a warm swimming pool. We told the front desk but they thought 35 deg C was fine. We hope to do this again and will definitely contact DF.
United States
We just got back this very minute from the Montelciano loop. Biking seems to be very popular with tourists here. Everything is going just great. The electric bikes are a dream for us older folks and Guiliana could not have been more helpful. Having a real good time here- thanks for everything !
Tracey
Canada
Cycling Tuscany was amazing!!! - bike routes were excellent. We really enjoyed the scenery, and the routes were a perfect mix of hills and enough breaks between. The instructions were excellent, they clearly let us know what to expect, and when. We found our approx 50 km to be just right. Yes, we could have done more, and sometimes finished fairly early, but the towns were so interesting, we know we would have been disappointed if we had less time to tour towns. - our hostess, Guilianna, was excellent. She gave us a great orientation, along with good dinner recommendations. We had a flat the first day, and a broken zipper on the bag, and she had replacements to us first thing the next morning. - the bikes were great. Very low geared, which made the hills so easy (think I should re-gear my bike at home! Lol!) Good quality bikes, nice and light - the breakfasts were really good. Much, much better than France. Doug was very hungry in France, they did not seem to understand Celiac. The gluten free bread served at breakfast in Tuscany was so good! We want to find a way to import the bread to Canada! - we also liked the hotels better. They were in vibrant towns, with lots to do. In Bordeaux it seemed we went to our hotel and that was it. Ate dinner and went to bed. The hotels in Tuscany were of excellent quality.
Australia
We really enjoyed the tour. Gigi and Giuliana were great and they gave us all the information we needed. The bikes were superb (the best we have ridden) and really well-suited to the hilly terrain. There are a few minor details to correct in the notes and we'll send them through to Gigi and Giuliana. The newer Garmin GPS was also really good although it took me some time to understand the display and how it worked. We knew the riding would be a bit harder than on some of our other Discover France tours and that proved to be true. The first day was hot and hard - it would have been tough if it was any hotter. Even though I do a lot of riding back home, I was apprehensive about cycling in Italy because of the fast traffic (I travel to Rome regularly for work and have had far too many fast taxi rides). Most drivers in Tuscany were fine although even the secondary roads had more traffic than we expected.
Australia
We had a good trip. The hotels and the meals were excellent. We had different expectations of the biking... and we're not up to the task. We didn't bike the last two days... partly because it rained pretty hard on us and partly because we were too tired. It's an absolutely gorgeous bike ride, and I want to explain our circumstance to you more fully when we get home. The people in charge of us here in Italy: Juliana, gigi, and Marco were wonderful, helpful and kind.
Canada
Overall the tour was amazing. Some of the destinations were a bit more touristy than last year(we like the beauty and hospitality of locals) but to be expected in Tuscany. The orientation was very good, the guides took the time to explain the bikes, garmin and maps. We really appreciated the call from Giulliana on the evening of day 2 to check up on how we were doing....nice touch. The bikes were great. The destinations and hotels were very good. We quite like the charming boutique hotels that give us a flavour for the town and local food. The NH Hotel in Sienna was nice, but we prefer the Pienza and Montacino hotels.
Casual : Beginners and occasional cyclists. Easiest tours we provide. Typically flatter terrain, no notable hills or anything of a steep gradient.
Hobby : Weekend riders. People with some cycling experience, rolling countryside, possible short climbs.
Active : Cyclists with experience on longer rides. Hilly terrain with reasonable amount of climbs and difficulty
Pro : Avid cyclists, ride every week and love long and challenging rides. Dream on riding the Tour de France cols.
Comparison chart : (15km/hrs)
| Average dist (miles) | Average dist (km) | Elevation max/day (m) | Average hours | |
|---|---|---|---|---|
| Casual |
< 28 | < 45 | < 300m | 3-4 |
| Hobby |
18 - 35 | 30 - 55 | 300-550m | 3-5 |
| Active |
30 - 60 | 50 - 100 | 550-1000m | 4-6 |
| Pro |
> 60 | > 100 | > 1000m | > 5 |
Some of our tours can be in 2 different level, we have itinerary for both versions
Casual : Beginners and occasional hikers. Typically flatter terrain with just rolling hills.
Hobby : Weekend hikers. People with some experience hiking around trails.
Active : Hikers with experience on longer hikes. Hilly terrain with some steep gradients.
Pro : Randonneurs avides, randonnée chaque semaine et adore les longues et difficiles randonnées.
Comparison chart : (4km/hrs)
| Average dist (miles) | Average dist (km) | Elevation max/day (m) | Average hours | |
|---|---|---|---|---|
| Casual |
< 6 | < 10 | < 150m | 2.5 |
| Hobby |
6 - 9 | 10 - 15 | 150-300m | 25-375 |
| Active |
9 - 11 | 11 - 18 | 300-450m | 3.75 - 4.5 |
| Pro |
> 11 | > 18 | > 450m | 4.5-6 |
Some of our tours can be in 2 different level, we have itinerary for both versions