Tuscany hill town the best of
We put together this short bike tour- 3 full days of cycling and one half day – for those who do not feel like taking a vacation entirely on a saddle.
wow moments
- 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.
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.
You can choose between Carbon frame race bike, hybrid, high-end E-bike and Gravel… to enjoy at the best pace!
Same place to stay but 7 nights with more loop: have a look at southern Tuscany bike tour
DAY 1
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.
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
Total Distance 20 km | +283 m / -288 m
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…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.
Distance: 53.5 km | +1068 m / -1070 m
DAY 3
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.
Distance: 44.4 km | +920 m / -876 m
DAY 4
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.
distance 55.2 km +880 m / -1076 m
DAY 5
End of bike tour after breakfast
INFO TOUR
best period From March to October
DIFFICULTY medium
TOTAL DISTANCE 173 km / 108 miles
TOUR REVIEWS
Price & Inclusions
Price
Cost: € 1190 per person in double occupancy
Single room supplement € 550
Inclusions:
Four nights in excellent three-star superior hotels
Four breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Maps with elevation gain
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 € 150 | E-Bike, road bike & Gravel € 180 | E-gravel € 250
City Tax each village charge a tax per each day between euro 0,70 to 3,00
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.
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.
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.
Mastrojanni Wine Relais is a wonderful place to experience one of the things we love most about this part of Tuscany: the close connection between cycling, landscape and wine. Set within the renowned Mastrojanni Brunello estate, the relais sits in a spectacular panoramic position surrounded by vineyards and the rolling hills of the Val d’Orcia.
We particularly like the feeling of staying right where the wine is produced, while enjoying the comfort and relaxed elegance of a beautiful wine relais. Its location, not far from the Abbey of Sant’Antimo and some of our favorite cycling roads around Montalcino, makes it a very special stage!
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,
Although it has been months since our cycling trip, I remember it vividly! It is one of the best organized trips I have ever been on!!
We had a fantastic time! The weather was beautiful and scenery spectacular!
The cycling routes you set up were low traffic and very scenic. Tuscany is every bit as beautiful as the movie! The route distance was perfect (30 to 40 miles). There was enough time to get started at a leisurely morning time and back to relax for a wonderful Italian dinner and some wonderful wine. The first day we had a little rain, but this was the shortest day so this worked out well. The GPS maps and the tourist information with recommendations was great and provided useful information. Yes, the course was a little hilly, but anything is hillier than central Illinois! The bikes provided were all in excellent condition and were great road bikes! Your pump worked perfectly and there were never any issues.
The hotels were all 4 or 5 stars and had great meals included. They were all located in excellent places, walking distance to sightseeing, restaurants, grocery stores, or laundromats. The hotels were accommodating with our bikes and very friendly and great hospitality! Our luggage was picked up from the hotel and was always at our new location.
Thank you to the gentlemen (I’m sorry, I do not remember his name) who picked us up from the train station, fitted our bikes, gave us the maps etc. He did a great job with the bike fitting and getting everyone individual attention!
I have recommended your outfitter group to another group from Central Illinois. I bet they will have a wonderful time too!
Thank you for your attention to detail and being such wonderful ambassadors to cycling and Italy!!
Grazie!
Brenda
Hi, Giuliana! We had a wonderful trip. Everything went smoothly and it was the trip of a lifetime! We are now in Florence for a few days and home on Sunday. Again, we had an amazing time and will recommend Cicloposse to our friends. I did post a recommendation for Cicloposse on Trip Advisor, and also on my blog, http://www.europe2wheels.blogspot.com Grazie.
Giuliana and Marco, I just wanted to send you a note to let you know how much we enjoyed the Cycling Trip in Tuscany!! EVERYTHING was wonderful, the hotels, the maps, the suggestions on restaurants and where to visit and especially the cycling. We had such a wonderful time and will definitely be back someday to ride even more!!
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