Tuscany - Self Guided
Bike Adventure Italy, the best of Tuscany by bike
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!
Wow Moments
- 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
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!
DAY 1
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
DAY 2
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!
Distance 53,5 km / 33,4 miles | +1068 m / -1070 m
DAY 3
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.
distance 54 km / 34 miles | +791 m / -792 m
DAY 4
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.
distance 44,4 km / 27,7 miles | +920 m / -876 m
DAY 5
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 47,3 km / 29,5 miles | +781 m / -782 m
DAY 6
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.
Distance 31 km / 19,4 miles | + 699 m / – 700 m
DAY 7
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.
Distance 55,2 km / 34,5 miles | +880 m / -1076 m
DAY 8
End of tour after Breakfast
optional bike ride in chianti to Castello di Brolio
INFO TOUR
best period from March to end of October
DIFFICULTY moderate to Difficult
TOTAL DISTANCE 320 km in 6 stages
TOUR REVIEWS
Price & Inclusions
Price
Cost: € 1620 per person in double occupancy
Single room supplement € 650
Luxury version price on request
Inclusions
Seven nights in excellent four & three-star superior hotels
Seven breakfasts
All Baggage transfers
RideWithGPS App: tracks, off-line navigation
Trip notes: Sightseeing & meals suggestions
Delivery bike at Pienza hotel & bike fitting
Pick-up of bikes and gear in Siena
Keepsake Cicloposse water bottle
Sales taxes
Not Included
Bike Rental per entire tour
Hybrid bike € 200 | Road Bike, E-Bike, Gravel € 280 | e-gravel € 380
City tax each village charges a tax per each day between euro 0,70 to 2,00.
Cloister is one of those places where you really feel the history of Pienza. Set in a former 15th-century convent directly on Corso Rossellino, the town’s main street, it still retains the atmosphere and character of the original building, with its beautiful cloister at the heart of the property. What we particularly love is the garden at the back, with its swimming pool and wonderful views stretching across Val d’Orcia. You are right in the center of Pienza, with cafés, restaurants and little shops just outside the door, yet once inside, the hotel feels remarkably peaceful.
Vecchia Oliviera is one of our favorite choices for a self-guided stay in Montalcino. Located just inside the historic center, next to one of the ancient town gates, it is very convenient to reach by bike while restaurants, wine bars and the lively streets of Montalcino are all within easy walking distance. We particularly like its panoramic terrace, where breakfast is served overlooking the surrounding countryside, and the lovely small outdoor pool – a very welcome treat after a day on the bike. Comfortable, friendly and perfectly located for cyclists.
Villa STR is a great choice for a cycling stay in Siena. Set in a 19th-century villa just outside the busiest part of the historic center, it combines a quiet setting with the convenience of being only about a 10-minute walk from Piazza del Campo.
For us, its location works particularly well: once you arrive, the bikes can be safely stored in the hotel garage and you are free to explore Siena entirely on foot. After the lively streets and squares of the city, the peaceful garden is a lovely place to come back to and relax.
For those looking for a more refined and intimate stay in Pienza, La Bandita Townhouse is our luxury upgrade. This small boutique hotel occupies a beautifully restored historic building right in the heart of town, combining the character of old Pienza with contemporary Italian design and a wonderfully relaxed atmosphere. We like it for its stylish interiors, spacious and comfortable rooms, and the personal feel that comes with a small boutique property. Step outside and you are immediately in the historic center, with Pienza’s restaurants, cafés and charming streets all within a few minutes’ walk.
For those looking for a little extra comfort, Palazzo Saloni is a wonderful upgrade in Montalcino. Set right in the historic center yet quiet and peaceful, it offers spacious suites, beautiful views over the Val d’Orcia and the convenience of having restaurants, wine bars and shops just steps away. We particularly like it for our cycling tours: you can arrive and leave directly by bike, and the hotel has a dedicated bike room. A perfect combination of comfort, location and cycling practicality.
For those looking for a more luxurious and peaceful stay in Siena, Certosa di Maggiano is a very special upgrade. Set in a beautifully restored 14th-century monastery just outside the ancient city walls, it combines centuries of history with contemporary design, spacious surroundings and exceptional comfort.
What we particularly love is the sense of space and tranquility – you feel immersed in the Tuscan countryside while still being just minutes from the historic center of Siena. The beautiful grounds and swimming pool make it an especially welcome place to relax after a day on the bike.
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Tour Reviews
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.
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
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