Tuscan lifestyle bike tour

Welcome to the bike trip combining fantastic moderate bike rides and cooking lessons, special tasting: olive oil, wine and cheese.
La  cucina Toscana – simplicity in its purest form.

Tuscany cooks take advantage of the freshest seasonal products and tamper with their natural state as little as possible. The cooking and the cycling aspects will please anyone who has a strong interest in one or both of these great passions.

Be aware that in Italy a genuine  meal can tell the story of local culture.

A variety of bike rides pursuits get you deep into some of the world’s most iconic and famous landscapes, while a sampling of food and drink experiences keep your mouth watering as you dig into the real way Tuscan people eat.

One cooking lesson will be about local fresh Pici pasta – read about in our blog

You will explore gorgeous loop rides in the beautiful val d’orcia, Unesco site since 2004:  Pienza, Montalcino, San Quirico. Not-to-be-missed San Casciano dei Bagni, Discover le Crete Senesi: a rolling sea of  land, sightsee the gothic  Siena town.

Each mail will be paired with a Tuscan wine: besides the must Brunello, Nobile and Chianti classico you will learn about and sip  Morellino di Scansano, Super Tuscan & Bolgheri, Orcia doc, Vin Santo, Syrah di Cortona.

How much cooking will we do?

After you have worked up an appetite, we will feed you very well! Most days include a hands-on cooking class or a visit to taste local food artisan. Our dining-out experiences range from a simple osteria, to a family trattoria, and an elegant restaurant. You will come home inspired, not only with new recipes, but also with the enthusiasm to cultivate these lessons into your lifestyle.

Which bike?

Carbon frame road bike, hybrid, gravel E-bike ALL YOU NEED IS TO CHOOSE,


  • Return from your trip with actual know-how to create a Tuscan dinner back home—it’s the ultimate keepsake!
  • Pedal rolling hills past Sangiovese vineyards
  • Enjoy Brunello wine tasting AND LUCNH AT CELLAR 
  • Eat Hand-rolled pici pasta, pecorino cheese, olio nuovo fresh-pressed olive oil, truffles, porcini mushrooms, Chianina beef, and cinghiale wild boar
  • Cycle the picture-perfect Crete Senesi, a route lined the waves of golden wheat fields and solitary cypress trees

At A Glances:

DAY 1-2 Immerse yourself in the beauty of southern Tuscany’s Val d’Orcia region | Explore the UNESCO World Heritage site of Pienza, renowned for its pecorino cheese and Renaissance architecture | Ride along scenic cypress-lined roads, soaking up the undulating landscapes | Indulge in Tuscan delicacies and relax at our charming country house.

DAY 3: Embark on a thrilling climb to Montalcino, a picturesque wine village offering breathtaking views | Enter the enchanting Crete Senesi area, characterized by its chalk hills and charming farmhouses | Experience farm-to-table Tuscan cuisine at a local agriturismo | Enjoy a sunset aperitivo at la Foce

DAYS 4-6 Traverse the captivating landscapes of Crete Senesi, reminiscent of Renaissance paintings | Cycle through sun-drenched pastures, olive groves, and oak woodlands | Discover the treasures of Siena at your own pace | Ride amidst the renowned vineyards of Sangiovese | Visit San Casciano, hot thermal town


Friday: Welcome to Val d'Orcia

Meet at Chiusi train station (a major stop on all the Rome-Florence lines) at 13.00/ 13.30
Private van transfer to the country house Palazzi del Papa , 14 km /9 miles from Pienza
Check in at your room and let’s start bike fitting session and meet your guides.
After all guest are set with bikes and equipment let’s have a very short bike ride test in the valley.
Ready for your first cooking session with Paolo – perfect way to build the team.
Hands-on lesson: prepare fresh pasta as primo piatto, appetizer, tiramisu; after a rest with a Italian spumante metodo Classico sparkling wine as aperitif, let’s share the table with all guest and savor the welcome dinner.

Saturday: Montalcino & Brunello

Our ride start 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. It is a tiny village, water has a constant temperature of 51 degrees Celsius, at the heart of the village is the "Square of sources", namely 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. Last effort -9 km gentle up to Montalcino - the hill town is very famous for Brunello wine made with the Sangiovese Grosso grape and aged a minimum of four years. After the visit let’s reach all together Solaria winery winery: you will taste their Brunello wine, the rosso and the supertuscan. Learn about the aging and enjoy the lunch at cellar.

Distance 48 km /30 miles



Sunday: Pienza, Montepulciano & cinta Senese

starting from the country house , first stage is Pienza, a pristine Renaissance jewel created 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 is the pecorino the delicious pungent cheese made using only sheep milk – continue to next village Montepulciano known as the Pearl of the Sixteenth Century.
our lunch will be at Fattoria Madonna della Querce a small farm specialized in cinta senese pig.
after learning about the traditional black pig, what they eat and live and how is fine the meat you will enjoy this special meal ending with vin santo & cantucci
Back in the saddle last stop in the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the Orcia valley where you bike through the fields that inspired Renaissance painters.

Distance 46 km /29 miles


Monday: San Casciano & Spa day

After welcome breakfast ready to start from the country house: across completely the Orcia valley. Pass 2 small villages Contignano ad Celle sul Rigo and get destination: the hot spring town San Casciano dei Bagni The spa is very old and in town there is impressive town hall of renaissance time. The historic centre worth a visit with its characteristic hill town-plan of alleys and small piazzas. Let’s enjoy the thermal pool, with a series of powerful swan neck jets, a stunning waterfall for intense natural massages, and the healing power of the hot springs, our Therapeutic Pool promises a journey into revitalization unlike any other

Total Distance km 36/22,5 miles


Tuesday: Radicofani, Pici & Pecorino

Today another terrific bike ride: start from villa reach Radicofani a medieval and enchanting village with a 1000 dating Rocca, one of the most impressive fortresses in Tuscany. Radicofani is included in the Park of val d’Orcia – Unesco site and Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), bust still is off the beaten path – so will be the most quiet day - from Radicofani now we will reach another secluded road called le Conie and reach Bagni San Filippo Enjoy the downhill back to the valley. It rise along Francigena road near the old Spedaletto Castle, shelter for wayfarer which, in the Middle Ages, wanted to get to Rome from all over Europe, in the XV century. Castle was readapted in a granary, a real fortified farm. On the way back let’s stop at the cheese farm to taste the delicious Pecorino di Pienza, 100% sheep milk with variety of aging.

Distance 55 km /34 miles

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, local Orcia red wine to sip

Wednesday: Siena & Le Crete

After breakfast departure by bike from the villa. First stop is San Quirico, an Etruscan origin village with a superb example of the Italian garden: the Horti Leonini. Pass through Asciano and Le crete area, with strange rock formations and lone farmhouse flanked by twin cypress tree. Let’s pedal through vineyards and forest we'll arrive in Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. Here we'll have time to shop while exploring the many hidden medieval walkways. Go soon to visit the shell shape square where the Palio horserace is run and enjoy a free lunch on your own.

Distance km 60 /37,5 miles


Thursday : Arrivederci al prossimo bike tour

After a breakfast all together there will be transfer to Chiusi train station around 10.00/11.00
On request we will arrange transfer at different time.
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Podere Palazzi del Papa
The Palazzi del Papa farmhouse was built in the thirties by the Marchesa Origo - La Foce - replacing an old inn where the Eminences used to rest when they were going through the nearby Francigena road.

Podere Palazzi Del Papa - Room
Furnished with rustic antiques, the country house has a warm atmosphere authentic Tuscan charm.
The Agriturismo has 9 double/twin bedrooms With en suite facilities with both showers and baths
Podere Palazzi del Papa - Garden
The Country house stands in the centre of the natural reserve of Lucciola Bella, in the heart of the Orcia valley - Unesco site since 2004
Podere Palazzo Del Papa - room close up
This marvelous 17th century Country house belongs to a large estate property of Nardi enzo
Podere Palazzo Del Papa - Breakfast
Nowadays, the Company owns 100 ha cultivated with cereals and wheat which is mainly used for the Chianina-breeding. This activity is, among others, the most important one.
Podere Palazzi del Papa
From the vineyards a wonderful red DOC Orcia wine is produced. Of course, it is available to be tasted for all our kind guests. They produce wine, olive oil, Chianina meat.

Cycling Tuscany

Price & Inclusions 

Cost: Euro 2900 per person in double occupancy
Single room supplement euro 490


Six nights in private villa;
Six dinners & Two lunches
two cooking classes;
one wine tour;
one cheese tasting;
All maps, trip notes and detailed route directions;
All Shuttles and technical assistance;
Support Van;
Services of experienced guide;
Cicloposse water bottle;
Transfer on day one from station;
Transfer on day seven to the station
Sales taxes

Not included
Airfare to Italy, train to Chiusi, 5 lunches, beverages, gratuities, travel insurance, laundry expenses and items of a personal nature

Bike Rental for entire tour
Hybrid bike   euro 180;  Road bike, gravel, E-Bike            euro 250


Tour Reviews

13 January 2018

Hi Giuliana,
Blaine and I wanted to write you a quick note to thank you for hosting us on our recent Active Tuscany Cycling Adventure.
Everything about the tour was exceptional from the towns in Tuscany that you selected us to ride, the restaurants that you selected for our dining and of course the professional chefs you had for us to learn the secrets of Tuscan Cooking!….
As you know, we thought Sabrina was beyond AWESOME! What an incredibly genuine and lovely women. I smile every time I think of her….so very precious!
Paula was an exceptional chef and now whenever I cook pasta, I hear Paula in my head explaining the “Tuscan” way to cook pasta….so delicious!
Gigi was a great cycle leader who did a super job having 6 riders all at different levels of fitness, experience and bikes. I can only imagine how challenging it is to get everyone to the same place, on-time without injuries….although I am sure we frustrated him (from time to time) he was always professional and guided us with his immense skill and expertise.
Andrea for only being with you a short time was so incredibly personable. What I admired most about Andrea is his ability to show initiative and his thirst for learning….learning about driving, bikes and always wanting to ensure that he was speaking grammatically correct english. Very impressive young man!
We also had the opportunity to dine on our last evening with your son who represented your company very well with his keen personality. Lovely young man!
Giuliana, you are the glue that holds all of this together and I want to thank you for your guidance and expertise.
Giuliana, you are a gracious host with a fantastic personality that made our adventure with Cicloposse the best cycling trip we have ever been on! Thank you!
We look forward to cycling with you again.

26 October 2016

Giuliana and Marco Wanted to thank you for a fabulous time in Tuscany. Jeff’s first trip to Europe and my first to Tuscany was made fabulously memorable and that is thanks to you both. We were so pleasantly surprised by the accommodations, by Duccoi, his family and staff and by your professional yet fun expertise and by everyone who helped make our experience so enjoyable. We will be return customers – guaranteed! (keep us in mind for Croatia for next September!) Gracie once again – Arrivederci fino alla prossima Volta!

26 October 2016

We had a absolutely fantastic time. I expected the riding to be great but had no idea all the rest of it the week would be so wonderful. Boscarello is beautiful, of course, but in addition Carlotta was a wonderful hostess and it was exciting to meet her father as well. The food was delicious — we’re still remembering and talking about the recipies! You and Marco were absolutely the best! All the riding details we so well thought out — we loved the restaurants and the visits. It was perfecto!! Thanks very much for everything. We really look forward to doing it again!

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