Tuscan Wine Classic: Pienza to Castellina via Siena
6 nights from €1770
4.83Cycle to Renaissance Gems, Vineyards, and Historic Abbeys in Italy's Rolling Hills of Tuscany
Yes, there are hills, but your efforts on this tour will be rewarded with sunny Mediterranean ambiance and a spirited flair for hospitality. Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.
The route takes you along tranquil country lanes tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys, and medieval forts. Staying in Pienza, Montalcino, Siena, and the heart of Chianti, you are sure to experience the true essence of Tuscany, where history and beauty fill the heart as water fills a well.
We suggest, after spinning through rolling vineyards, golden wheat fields, and chalky white hills by day, that you spend your evenings savoring pecorino cheese, homemade pasta pici, fruity olive oils, and sipping the Tuscan wines Brunello and Nobile.
This tour immerses you in Tuscany!
Upon request longer routes can be provided as well (55-63 miles per day).
Daily Program
Day 1: Pienza
Meet and greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza is a remarkable example of renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it's a real treat to stroll around its cobblestone streets. Take an optional test ride to San Quirico d'Orcia (13 miles/20 km).
Overnight in Pienza
Day 2: Pienza – Montepulciano and vino nobile
33 miles/54 km
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed and in the enchanting little hamlet of Castelmuzio. By lunchtime, you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
Elev. + 1068 m / - 1070 m
Overnight in Pienza
Day 3: Pienza – Montalcino brunello land
28 miles/45 km
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked.
Elev. + 920 m / -876 m
Overnight in Montalcino
Day 4: Montalcino – Siena and Monte Oliveto Abbey
36 miles/58 km
Today will take you through the typical postcard scenery of Tuscany, Italy’s most photographed region. 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. Afterward, 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.
Elev. +1035 m / -1217 m
Overnight in Siena
Day 5: Siena – Chianti hills
35 miles/56 km
Ride from Siena to Castellina in Chianti, following the "Chiantigiana" road. Along the way, you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlets. Not far away is Castello di Brolio, a castle and winery that you can visit. There's also the chance to shop at a first-class ceramics workshop. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get to Castellina.
Castellina's medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants.
Elev. + 1019 m / -787 m
Overnight in Castellina in Chianti
Day 6: Castellina – Greve in Chianti and Panzano
34 miles/55 km
Circular bike ride to Florence Chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honey, and rich olive oil. Have a stop at Greve's main piazza, which is characterized by an original formation of irregular triangular shape and defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate, and the keep of the medieval castle, relax by the vanishing edge pool spilling into the countryside of endless vineyards.
Elev. +1019 m / -1019 m
Overnight in Castellina
Day 7: Castellina
Individual departure
Hotels
These are sample hotels and may vary based on availability.
Standard hotels
The accommodations are 3- and 4-star hotels.
Pienza: Relais il Chiostro
Montalcino: Hotel Vecchia Oliviera
Siena: La Villa STR
Castellina: Hotel Palazzo Squarcialupi
Luxury hotels - available on request
Pienza: La Bandita
Montalcino: Relais Mastrojanni
Siena: La Certosa di Maggiano
Gaiole: Castello Di Spaltenna
Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.
Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.
Bikes
Standard touring bike
Frame: Aluminum frame
Fork: Full carbon
Chain ring: Shimano Deore – triple or compact
Cassette: Shimano Deore – 11/34 or 11/36
Brakes: Shimano Deore
Saddle: Selle Italia XO & lady gel
Wheel set: Shimano RS30
Tires: Panaracer close
Weight: 9,5 kg
Size: We can fit riders from 5.0 to 6.4 ft / 1,50 to 1,95 m
Size frame from 46cm to 62cm
Road bike
Frame: Full carbon frame
Fork: Full carbon
Chain ring: Shimano Ultegra compact 50/34
Crank: 172.5 / 175.00 mm
Cassette: Shimano Ultegra or 105 – 11/32 – 11 speed
Brakes: Shimano Ultegra rear and front
Saddle: Selle Italia
Wheel set: Shimano R561
Tires: Panaracer Extreme
Weight: 7,6 kg
Size: We can fit riders from 5.0 to 6.3 ft / 1,50 to 1,92 m
Size frame from 46cm to 59cm
Gravel bike
SCOTT Addict Gravel 20
The SCOTT Addict Gravel has been set up to allow you to ride any road, anywhere and in any weather conditions.
A lightweight Carbon fiber frame, Equipped compact Ultegra, rugged Schwalbe G-One tires and Shimano Hydraulic disc brakes give you a rig that will let you get your adventure on, no matter what.
A cyclocross touring oriented 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.
Size: S, M, L , XL
CANNONDALE Topstone1 Gravel
Straightforward, reliable and a whole hell of a lotta fun, the Topstone Alloy is a gravel bike crafted for those with a taste for adventure – and value.
Roll light and free, or load it up for a long haul, Topstone’s comfortable ride, confident handling and up-for-anything capability make it the perfect partner on any road, anywhere.
A Lightweight frame and full carbon fork equipped with Shimano GRX 800/600 11-speed shifting
Size: XS, S, M, L, XL
Electric bike
Scott E-SUB Cross 10
E-sub cross 10 as the best for our tours: The SCOTT E-SUB Cross 10’s newly developed frame ePowered by a new 500wh Bosch Internal battery, will get you where you are going faster and more comfortably than ever before.
- Purion Display
- Fork: Suntour Nex-E25 Lo Ds 15mm Ta Tapered
- E-Drive System : Bosch Performance 250w System W
- 500wh Power Tube Battery
- Rear Derailleur: Sram Nx 11 Speed
- Brakes: Shimano Br-M365 Disc
- Size: S,M,L / Man & Woman Model
Electric bike
Scott E-SUB Cross 10
Meet the new Sub Cross eRIDE 10: equipped with the powerful Bosch Performance CX drive unit and a PowerTube battery intelligently integrated into the frame for a slick design.
An adjustable stem and the ergonomic Syncros saddle result in optimal comfort
- Intuvia 100 Display
- Front suspension: Suntour 63mm
- E-Drive System : Bosch Performance CX
- 625 wh Power Tube Battery /
- Rear Derailleur: Shimano Deore 10 speed
- Brakes: Shimano Br-M365 Disc
- Size: S,M,L / Man & Woman Model
Electric bike
E- bike Positive +
Positive + Performance Tecnobike is the elegant and highly performing electric trekking bike.
Equipped with a luggage rack and equipped with a powerful Shimano performance motor, the Positive e-trekking is the ideal bike for getting around for tourism by bike
- Purion Display
- Fork: alloy suspension fork 700C
- E-Drive System : Bosch Active Line Plus
- 500wh Power Tube Battery
- Rear Derailleur: Shimano Altus
- Brakes: hydraulic disc
- Size: S, M / step-through frame
Equipment included with bike rental:
- Helmet
- Handlebar bag or map holder
- Water bottle
- Repair kit (mini pump, inner tube, tire levers)
- Computer mileage counter
- Lock (one lock with key per 2 bikes)
Bike Protection:
Bike protection can be purchased at the time of booking. You can read more about that HERE.
Pedals:
The bikes will have toe clips or flat pedals. You can also bring your own pedals and shoes, along with the necessary equipment for installing the pedals.
Seats:
If you plan to bring your own seat, please don't bring the seat post. The tour company can assist you with installing.
Helmets:
Helmets are required on this tour. Helmets are included in the tour package; however, we recommend you bring your own helmet for safety and hygiene reasons.
Surface and terrain
There are lots of ups and downs on rolling hills and some climbs and challenging hills. The terrain is rarely flat.
Roads:
90 % are on small country roads( no cycle path). You will encounter a little more traffic when entering the villages and towns, you will see this especially going in and out of Siena.
How to get there
Tour start
Nearest airport: Rome Fiumicino (FCO) and Florence Peretola, Italy (FLR)
Nearest train station: Chiusi-Chianciano, Italy
From either airport, take a train to Chiusi (www.trenitalia.com/tcom-en). Once in Chiusi, you can take a bus or taxi to get to Pienza. Take the bus from Chiusi to Montepulciano. The bus fare is approximately €4 per person, and the bus leaves every 30 minutes (40-50 minute ride). From Montepulciano, take the bus to Pienza (15-minute ride). Please note the bus from Montepulciano to Pienza is not available on Sundays.
Tour end
Nearest airport: Florence, Italy (FLR)
Nearest train station: Castellina, Italy
At tour end, buses and trains are available. By bus, go to Siena station where you can take a direct bus or train to Rome or other destination.
Tips on getting to and from your tour
Reviews
- ★★★★★ Claudia Lutke
The best way to have an immersive experience in Tuscany
The route, the bikes, the hotels. All received an A+ grade. Except the part of arriving in Pienza and leaving Castellina. The topic “How to get there”, part of a e-mail sent by you should be improved. The option TAXI from Chiusi train station doesn’t exist. No taxis there. There is only one bus/day to Pienza that departures in the morning. And we arrived in the afternoon. After asking four different people we realized that the only way available would be to take a bus - a city bus, not prepared for the transport of passengers + luggage - to Montepulciano and then find a way to arrive in Pienza. We thought that we could take a taxi there. But no taxis either. Fortunately, cel phones were charged and with internet access, so we contacted the local operator, explained the situation and they went to “rescue us”.
The same uncertainty happened by the time we left Castellina. We had 4 bags (it was a 20 days vacation trip, with different activities, including a meeting in between - with a “social” dressing code). It would require a considerable effort to carry the luggage until the bus stop, to take another city bus until Siena and then find a way to go to Florence (the place where we would continue the trip). The lovely cities that we visited in Tuscany are in fact villages. There are no taxi services overthere.
Again, the tour operator helped us passing the contact of a private driver who led us from Castellina to Florence.
My suggestion: include the transfer to the starting point and from the finish point in the “to do list” for the local operators when cities have such a limited options of transportation.- What was the date of your tour?
- Oct/Nov 2025
- How many tours have you completed?
- 5
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists
- Do you recommend this tour?
- Yes
- ★★★★★ Michael Burkardt
Beautiful Countryside
Our Bike Tour Company Cicloposse was exceptional, the best we ever had. There was not a single detail they missed, providing a booklet covering highlights for a given day of each town we'd pass through and as well as where to eat. We had a minor issue that was no fault of their own and the customer service was top notch. They're professional and knowledgeable. The only hiccup was a closed bridge that added a hour to our ride that day. Warning: unless you are a very strong rider get an E bike. Some climbs are miles long with a 14% grade.
- ★★★★★ Amanda De Wet
Best holiday ever!
Tuscany is beautiful, and it was amazing exploring by bike. We had the best time! Organization was excellent, local company was amazing and helpful, hotel accommodation was perfect - really cannot fault anything. Highly recommended!
- What was the date of your tour?
- July 2022
- How many tours have you completed?
- This was our first.
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists, Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
- ★★★★★ Rasp
BEST honeymoon ever!
Well planned itinerary. Italian Guides were very friendly and knowledgeable and Set us up quickly and efficiently. Accompanying materials had great suggestions and option to do long or short ride every day was terrific.
- What was the date of your tour?
- October-nov
- How many tours have you completed?
- Several
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
- ★★★★★ Snowball
Best local bike company ever!
The local bike company were responsive to our needs and provided really excellent bikes. Accommodation was inspired.
- What was the date of your tour?
- July
- How many tours have you completed?
- 15
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- Solo travelers, First-time bike tourists, Families with teens
- Do you recommend this tour?
- Yes
- ★★★★★ Rotsen
A great way to embark on the endless search for a bad Tuscan wine.
The only thing that wasn't absolutely perfect on this trip was the weather. The bikes provided were new and light, 25c tires, Shimano 105 11sp compact group w/32T cog for easy climbing.
The route selection was wonderful, with a loop the first day to get acclimated and a loop the last day to provide options. The route cue sheets and maps included profiles and were spot-on so we hardly even bothered using the GPS routes they gave us to upload. We didn't have as much freedom to actually "tour" and stop at all of the sites as we usually do on tours due to the nearly constant threat of rain. Still we mostly avoided the rain until it arrived within last 5 or 6 kilometers on three of the days.
The upside was that we had more time in the towns we spent the nights, for wine and cheese tastings, and of course Gelato (If you ever come across Pear-Pecorino-Honey gelato don't be shy.) The hotel accommodations were terrific! Our luggage always made it there before we did. The breakfasts, the only meals included, were above par Continental with great coffee and, at the least, hard boiled eggs.. A number of times we ate dinner at the Hotel Restaurant. Following our arduous afternoon and evening searches for bad wine we kind of liked being close to our beds.
I am happy to admit that we failed utterly in our quest for a less-than-great Tuscan wine. We didn't bring any of the terrific Brunello's or Rosso's or Chianti's that we drank back, but did return home with 22kg of Pecorino Cheese most notably the Formaggio di Fosse. (My apologies to those who shuttled our baggage.) Someday soon we will return to continue our search, perhaps during a more dependably dry part of the year.
- What was the date of your tour?
- June 1
- How many tours have you completed?
- 8
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists, Families with teens
- Do you recommend this tour?
- Yes
More About This Tour
Related Bike Tours 
Cycling and Cooking in Sardinia
Italy 
Cycling and Cooking in Tuscany
Italy 
Custom and Private Bike Tours in Italy
Italy Related Day Tours
Chianti Classico Florence E-Bike Tour with Wine & Olive Oil Tasting
Florence 
Private Florence Bike Tour
Florence 
Classic Tuscany Bike Tour
Florence 
Street Food Bike Tour Palermo
Palermo 
Capuchin Catacombs Bike Tour Palermo
Palermo 
Email
Office Hours