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Tuscan Wine Classic: Pienza to Castellina via Siena

  • 5


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  • 6 nights | 32 miles/day
  • Difficulty Level: 4
  • Self-guided from: €1290
  • View Dates

Tours using road, hybrid or touring bikes:

  1. Mostly flat
  2. Flat with some gentle slopes
  3. Rolling, hilly terrain
  4. Some long and/or steep climbs
  5. Extensive climbing

Tours using mountain bikes:

  1. Mostly flat, wide trails
  2. Some gentle slopes, wide trails
  3. Rolling, hilly terrain and/or narrow trails
  4. Some long and/or steep climbs and/or technical trails
  5. Extensive climbing and/or highly technical trails
  1. Variety: Choose from more than 200 tours offered by local operators in 35 countries.
  2. Advice: Our informed advisors help you choose the trip that's right for you.
  3. Lower cost: You pay local tour company prices—less than what big American companies charge.
  4. Great exchange rates: Pay low rates thanks to the millions of dollars in foreign currency we buy each year.
  5. Convenience: We handle the full booking and payment process.
  6. Support: We’re your advocates from initial planning through final pedal stroke.
Tour Type: Guided Self-guided

Tour description

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 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, to 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 reniassance town in the world, for welcome and bike fitting. Pienza is a remarkable example of reniassance-era town planning. If you have even the least appreciation for beautiful architechture, it's a real treat to stroll around it's 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 (34 miles/55 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.
Overnight in Pienza

Day 3: Pienza – Montalcino brunello land (29 miles/46 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.
Overnight in Montalcino

Day 4: Montalcino – Siena and Monte Oliveto Abbey (36 miles/58 km)
Today 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.
Overnight in Siena

Day 5: Siena – Chianti hills (31 miles/50 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 hamlet. 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.
Overnight in Castellina in Chianti

Day 6: Castellina – Greve in Chianti and Panzano (34 miles/56 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 honeys and rich olive oil. Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, 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 poolspilling into the countryside of endless vineyards.
Overnight in Castellina

Day 7: Monteriggioni (optional 20 mile/32 km loop ride)
The short bike ride allow you to visit Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around.

Route Map

Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route. Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route.


Daily: Mar 15-Oct 31, 2019


Tour package
Per person, double occupancy
Single room surcharge (1 person/1 room)
Bike Rentals
Hybrid touring bike
Road bike
Electrically assisted bike
Please note: Instead of operating bicycle tours ourselves, represents local bicycle tour operators around the world. Review the tour operator's information and terms below, then submit your booking request through The primary benefits of booking your tour through include:
  • Lower cost: You pay local tour company prices—less than what big American companies charge
  • Variety: Choose from more than 200 tours offered by local operators in 35 countries.
  • Advice: Our informed advisors help you choose the trip that's right for you.
  • Great exchange rates: Pay low rates thanks to the millions of dollars in foreign currency we buy each year. Or pay in euros!
  • Convenience: We handle the full booking and payment process.
  • Support: We’re your advocates from initial planning through final pedal stroke.
Contact us with any questions about booking and paying for your tour through We look forward to serving you!

Cicloposse Terms and Conditions

In the event that you cancel your participation on the trip, the tour operator has the right to charge a penalty if the customer renounces his booking:

If cancellation occurs:

  • more than 60 days before starting date: no penalty (just handling charges of 19 euros plus .2 (point-2, not 2) percent of tour price)
  • between 60 and 45 days before starting date 30% penalty
  • between 44 and 30 days before starting date: 50% penalty
  • between 29 and 21 days before starting date: 70% penalty
  • within 20 days before starting date: 100% penalty

Cancellations by us
Scheduled guided tours with low enrollment may be subject to cancellation. Registrants will receive a forty-five day notice and full refund or option to move to another scheduled week. In very rare cases it may be necessary for the tour operator to cancel a tour. In the event of cancellation, a full refund will be sent to the client and this constitutes full settlement. The tour operator is not responsible for other expenses incurred such as pre-paid hotel reservations or non-refundable airline tickets. 

Trip Insurance
The tour operator strongly recommends cancellation and accident insurance to prevent any losses in case of illness, accident or otherwise. It is the responsibility of the client to apply directly to the insurance company. Please purchase trip cancellation insurance in case an illness forces you to cancel or depart early from a trip.

Clients are responsible for selecting a tour suitable for their athletic ability. They are responsible for reading all pre-trip materials, informing us of any medical or dietary restrictions, signing our release form prior to the start of their tour, and obeying all safe biking rules. The tour operator reserves the right to decline or withhold service to any person who, for physical or other reasons, is deemed unfit for the trip. Every care will be taken to respect your luggage at all times. However, the tour operator is not responsible for damage, loss or theft of your personal belongings


Our accommodations are in excellent four and three-star hotels and country inns. We will do everything in our power to secure you lodgings in our first-choice hotels, but it may not be possible if you are booking less than three months before traveling or during a particularly busy season. In that case we will secure you lodgings in comparable hotels. Tour prices are based on double occupancy. Additional nights can be arranged for early arrivals or late departures. Single supplements are available upon request.

Rental Bicycles
PROVIDED EQUIPMENT: 27-speed touring or race bikes, alloy frame with carbon fiber fork and equipped with Shimano high quality components; Helmet; Front handlebar bag; water-bottle & cage; Lock; Cycle computer; Repair kit, including spare tire; Pump; Toe clips.

We will ask for your measurements to insure that you get the most suitable bike possible, we strongly recommend you book as early as possible.

You will be responsible for the bicycle once you take possession of it at your first hotel. Your responsibilities include any costs for damage or theft up to the full value of the bicycle.

The tour operator and its representatives act only in the capacity of tour operators for land transportation, sightseeing and hotels which provide services included in the specified tour.

The individual tour participant agrees that the tour operator and its representatives shall not be liable for any injury, damage, loss, accident, delay, or irregularity, liability or expense to person or property due to any act of default of hotel, land transportation carrier, restaurant supplier or other contractor rendering or providing services. The tour operator and its representatives shall not be responsible for any expense or liability resulting from labor disputes, war, acts of terrorism, government restraints, weather conditions, sickness, pilferage or any other cause beyond their control. The tour operator and its representatives reserve the right to accept, or to retain or refuse any person as a participant of any tour or to cancel any program of a tour if circumstances so demand.

By submitting a booking request, I have and do hereby fully assume all risk of illness, injury, or death and hereby release the tour operator from all actions, claims, or demands for damages resulting from my participation on the trip. I agree that the foregoing obligation shall be binding upon me personally, as well as upon my heirs, executors and administrators and all members of my family, including any minors accompanying me. I have had sufficient opportunity to read this entire document. I have read and understood points above and I agree to be bound by their terms.

All photos used by permission. ©Cicloposse


Ratings Snapshot

  • 5 Star 3
  • 4 Star 0
  • 3 Star 0
  • 2 Star 0
  • 1 Star 0

Average Ratings

  • Overall


  • Difficulty level (Actual vs. expected) 3
  • Value 4.3
  • Included meals 5
  • Bikes & equipment 5
  • Hotels or boat 5
  • Scenery 5
  • Ease of navigation 4.7
  • Tour documents 5
  • Local tour company services 5
  • Route selection 5
  • Guides (if applicable) 5


Rasp November 24, 2017

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.

Snowball September 27, 2016

Best local bike company ever!

The local bike company were responsive to our needs and provided really excellent bikes. Accommodation was inspired.

Rotsen June 21, 2016

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.