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Cycling and Cooking in Tuscany

“The villa is spectacular, and every location we visited was special.” — EM

“The villa is spectacular, and every location we visited was special.” — EM

“The villa is spectacular, and every location we visited was special.” — EM

“The villa is spectacular, and every location we visited was special.” — EM

“The villa is spectacular, and every location we visited was special.” — EM

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

Welcome to the trip that combines fantastic bicycle routes and cooking lessons, all in Italy’s famous region of Tuscany. After you have worked up an appetite biking through the rolling landscape of Tuscany, you will cook and eat the best food!

La Cucina Toscana is simplicity in its purest form. Tuscan cooks have the freshest seasonal products at their disposal, including olive oil, wine and cheese, and do very little to alter their natural state. Most days will include a hands-on cooking class or a tasting at a local food artisan. You will also dine out at a simple osteria, family trattorias, and elegant restaurants.

Cyclists will explore gorgeous loop rides in beautiful Val d’orcia, passing such highlights as Pienza, Montalcino and San Quirico. The routes cross Val di Chiana, through Cortona to Crete Senesi and on to Siena.

Return home inspired, not only with new recipes to try, but also with the enthusiasm to cultivate the lessons you learn into your lifestyle!

Daily program

Day 1: Welcome to the Villa
Meet at the Chiusi train station (a major stop on all the Rome-Florence lines) at 1:00pm. Private van transfer to the country house Palazzi del Papa, just a short drive from Pienza. Check into your room and start the bike-fitting session and meet your guides. After all guest are set with bikes and equipment we'll have a short test bike ride in the valley. T

hen get ready for your first cooking session with Paola – a perfect way to build the team. You'll enjoy this hands-on lesson: preparing fresh pasta as primo piatto, appetizer, tiramisu; after a rest with a prosecco sparkling wine as aperitif, we'll share the table with all guest and savor the welcome dinner.

Day 2: Cortona (28 miles/45 km)
After a welcome breakfast, we'll have a short transfer by van to just outside Montepulciano village to begin the first ride with a nice gentle downhill through the vino nobile vineyards. After this will be flat terrain--the Val di Chiana, once a swampy lowland--except for the final climb to reach the old town on the hill Cortona, one of Italy's oldest towns.

The first set of city walls were built by the Etruscans in the 4th century BC. Cortona became famous by Frances Mayes's bestselling book (also a movie), "Under the Tuscan Sun." Stroll the winding – narrow and steep! – medieval streets for a while.

Transfer back to the country house by van in the afternoon (or stronger cyclists have an option to ride back)! Dinner in Monticchiello at La Cantina della Porta.

Day 3: Pienza, Montepulciano (29 miles/46 km)
Our ride today starts from the villa. The first stage is Pienza, a pristine Renaissance jewel, founded in 1458. Pope Pius II chose the famous Florentine architect Rossellino to transform his home village of Corsignano into one of the few examples left of 15th century architecture. The main product in this area is the pecorino cheese, a delicious, pungent cheese made using only sheep milk.

You'll continue to next village Montepulciano, known as the Pearl of the 16th Century. After lunch at la Porta di Bacco, you'll see some Etruscan caves and enjoy a wine tour at Cantine de Ricci and explore the underground wine cellar. This Cantina is right in the center of town just off Piazza Grande, and has been dubbed the most beautiful wine cellar in the world.

Back in the saddle, the last stop is the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where we bike through the fields that inspired Renaissance painters. Tonight you'll have dinner at Locanda in Tuscany.

Day 4: Montalcino and Brunello (30 miles/48 km)
Our ride starts from the villa: first stop after 10 km easy ride is the ancient Roman spa of Bagno Vignoni. Legend has it that Saint Catherine and Pope Pius II both bathed in the thermal waters here. The water has a constant temperature of 51 degrees Celsius (124 degrees Fahrenheit). At the heart of the village is the "Square of sources," a rectangular tank of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins.

Now the climb to Castiglione d’Orcia is the challenge part of the day. Once at the top, enjoy a long downhill till Romanesque abbey of Sant’Antimo that dates back to the time of Charlemagne. The final effort is 9 km gentle ascent to Montalcino – the hill town famous for Brunello wine made with the Sangiovese Grosso grape and aged a minimum of four years. After the visit we'll reach the Corte Pavone winery: you will taste this biodynamic and organic Brunello wine, learn about the aging process, and enjoy the lunch at the cellar. Return to the villa for the second cooking lesson.

Day 5: Radicofani and Pici (34 miles/55 km)
Today another terrific bike ride. Start from the villa and reach Radicofani, a medieval and enchanting village with one of the most impressive fortresses in Tuscany. Radicofani is included in the Park of val d’Orcia – a Unesco site and Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), but still is off the beaten path. This will be the quietest day.

From Radicofani now we will ride another secluded road called le Conie and reach Bagni San Filippo. Enjoy the downhill back to the valley. The valley rises along Francigena road near the old Spedaletto Castle, shelter for wayfarers who, in the Middle Ages, wanted to get to Rome from all over Europe. The castle was readapted in a granary, a real fortified farm.

We'll head back to the country house by bike. This afternoon let's learn the classic pasta of the area: pici all’ aglione sauce and pici al ragu di chianina. Pici is a fresh spaghetti, handmade one by one.

Day 6: Siena (38 miles/60 km)
After breakfast ride toward San Quirico, an Etruscan origin village with a superb Italian garden: the Horti Leonini. Pass through Asciano and Le Crete with strange rock formations and lone a farmhouse flanked by twin cypress trees.

Let's pedal through vineyards and forest and arrive in Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. Visit the shell shape square where the Palio horse race is run and enjoy lunch on your own. Back to the villa, you'll have time for a jump in the pool and a rest. We'll have our farewell dinner at a restaurant at la bandita townhouse.

Day 7: Individual departure
After a farewell breakfast all together, we will transfer you to the Chiusi train station around 10-11:00am. (On request we will arrange transfer at different time.)

Route Map

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


Apr 12, May 24, Jun 14, Sep 13, Oct 11, 2019


Local :

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Tour package
Per person, double occupancy
€ 2800
Single room surcharge (1 person/1 room)
€ 490
Bike Rentals
Hybrid touring bike
€ 180
Road bike
€ 210
Electrically assisted bike
€ 210
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