Cycling & Cooking in Tuscany

Cycling & Cooking in Tuscany

Cycling & Cooking in Tuscany

Tuscany - Guided tour

Tuscan lifestyle bike tour

Welcome to the bike trip combining fantastic moderate bike rides and cooking lessons, special tasting: olive oil, wine and cheese.

WOW Moments

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 & LUNCH 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

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?

Road bike, hybrid, gravel E-bike ALL YOU NEED IS CHOOSE

2024 departure

May 17-23   SOLD OUT
June 7-13   CONFIRMED
September 13-19  CONFIRMED
September 27 – October 3 SOLD OUT
October 11 -17  CONFIRMED
October 25 – 31  SOLD OUT

2025 departure

May 16-22
May 30- June 5 
June  6 -12  
June 21 – 27  
September 12-18
September 26 –October 2 
October 10-16
October 24 – 30





Cycling Details

Distance & elevation

Day 1 – Friday

Welcome to Val d’Orcia Meet at Chiusi train station at 13:00/13:30; Private van transfer to villa; Short bike ride test; Cooking session with Paolo; Fresh pasta preparation; Welcome dinner

Test ride

Day 2 – Saturday

Montalcino and the Art of Brunello Cycling journey through San Giovese grape landscapes; Visit to Montalcino and its Enoteca; Downhill ride to Castelnuovo dell’Abate; Wine tour and lunch at Tenuta Fanti Estate; Cooking lesson at La Pieve; Cheese and olive oil tasting; Dinner at villa

Distance: 40.0 km –

Elevation Gain: +698 m –

Elevation Loss: -817 m

Day 3 – Sunday

Charming Pienza and Montepulciano Visit to Pienza; Cycling through villages like Castelmuzio and Montisi; Picnic lunch; Transfer to Montepulciano; Free time; Dinner at la Porta di Bacco

 Distance: 38 km –

Elevation Gain: +763 m –

Elevation Loss: -764 m

Day 4 – Monday

Monticchiello & Bagno Vignoni Spa day Bike ride to Monticchiello; Visit to Bagno Vignoni; Picnic lunch; Thermal waters; Cooking lesson with chef Paolo; Dinner at villa

 Distance: 28 km –

 Elevation Gain: +387 m –

Elevation Loss: -529 m

Day 5 – Tuesday

Exploring Radicofani, the Legend of Ghino di Tacco Cycle to Radicofani; Visit to fortress and old town; Dinner at Abbadia Sicille At Fondo restaurant

Distance: 71.6 km –

Elevation Gain: +1147 m –

Elevation Loss: -1179 m

Day 6 – Wednesday

Siena & Le Crete Departure from villa; Visit to San Quirico and Asciano; Cycling through Le Crete area; Arrival in Siena; Free time; Lunch on own; Farewell dinner at la Bandita townhouse in Pienza

Distance: 47.0 km –

Elevation Gain: +672 m –

Elevation Loss: -900 m

Day 7 – Thursday

Arrivederci al prossimo bike tour Transfer to Chiusi train station around 10:00/11:00



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

Begin your journey with a private van transfer to your villa, a charming Tuscan accommodation. The villa is surrounded by vineyards, olive groves, and medicinal plants, providing the ideal setting for your adventure. Embrace the rich heritage of the Val d’Orcia, a UNESCO World Heritage Site, and be captivated by the enchanting Palazzo Massaini, a place where quality wines, oils, and spirits are produced.

After all guest are set with bikes and equipment let’s have a very short bike ride test

Ready for your first cooking session with Paolo – perfect way to build the team.

Hands-on lesson: prepare fresh pasta as primo piatto, 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 and the Art of Brunello

Saddle up for a 40 km cycling journey that takes you through landscapes reminiscent of a Renaissance painting. Pedal through the sea of San Giovese grapes, the heart of Brunello di Montalcino, and visit the city bearing its name. Montalcino’s medieval history is intriguing, with battles between Florentine and Sienese city-states, and a towering fortress built by the Sienese in the 14th century. Take a moment to explore Montalcino’s charming piazza and its Enoteca, dedicated to the exquisite Brunello wine. A gentle downhill ride awaits as you head to Castelnuovo dell’Abate to visit the Abbey of Sant’Antimo. Enjoy a wine tour and a light lunch at Tenuta Fanti Estate before returning to La Pieve for your second cooking lesson. The day concludes with a cheese and olive oil tasting, followed by dinner at the villa.

Distance 40.0 km elevation gain +698 m / elevation loss -817 m

Meals included:  breakfast, lunch & dinner


Sunday: Charming Pienza and Montepulciano

Venture out for a 38 km bike ride that includes a visit to Pienza, a town transformed into the epitome of Renaissance perfection by Pope Pius II. Explore the meticulously designed Piazza Pio II, adorned with a loggia, Palazzo Piccolomini, and the impressive Duomo. As you cycle through picturesque villages like Castelmuzio, Montisi, and Trequanda on secondary paved roads, enjoy a delightful picnic lunch in the scenic countryside. Complete your journey with the last 4 km on gravel roads before returning to La Pieve. The evening includes a transfer to Montepulciano Montepulciano, known as the Pearl of the Sixteenth Century where you’ll have.
Free time to explore the dignified hilltop town before a delightful dinner at la Porta di Bacco

Distance 38 km elevation gain  +763 m / elevation loss -764

Meals included:  breakfast & dinner


Monday: Monticchiello & Bagno Vignoni  Spa day

Embark on a bike ride to Monticchiello, a charming village with a medieval look preserved through the ages. Make your way to Bagno Vignoni, known for its ancient healing pool. Today a pic-nic lunche before you enjoy the thermal waters that have attracted travelers on the Via Francigena pilgrimage for centuries.

Explore the healing history of this remarkable village as you wander through the streets.

Ready for another cooking lesson wit chef Paolo? Ravioli, zucchini flowers, Tiramisù. All you need is an apron!

Total Distance 28  km  elevation gain  +387 m / elevation loss -529 m

Meals included:  breakfast, lunch & dinner


Tuesday: Exploring Radicofani, the Legend of Ghino di Tacco

Today another terrific bike Cycle through gentle uphills and rolling hills, leading you to the medieval village of Radicofani. Explore the impressive fortress, offering extraordinary panoramic views over the Val d’Orcia, Amiata, the Apennines, and the Trasimeno and Bolsena lakes. Uncover the tale of Ghino di Tacco, a charismatic gentleman bandit who roamed the Via Francigena, mentioned even in Dante’s Divine Comedy. Visit the Palazzo Pretorio and stroll through Radicofani’s stately old town. Conclude your adventure with dinner at Abbadia Sicille At Fondo restaurant, where history and cuisine come together to create a memorable evening.

Distance 71.6 km    elevation gain  +1147 m /  elevation loss -1179 m

Meals included:  breakfast & dinner


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.Farewell dinner at restaurant la Bandita townhouse in Pienza

Distance km 47.0 km  elevation gain  +672 m / elevation loss  -900 m

Meals included:  breakfast & dinner


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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Tour start meeting at Chiusi station
Tour end Chiusi station



best period spring and fall

DIFFICULTY easy to medium



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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Price & Inclusions


Cost: € 3200 per person in double occupancy
Single room supplement € 690


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   € 180;  Road bike, gravel, E-Bike € 250

2024 departure

May 17-23 SOLD OUT 
June 7-13  CONFIRMED
September 13-19
September 27 – October 3 CONFIRMED
October 11 -17 CONFIRMED
October 25 – 31  SOLD OUT


2025 departure

May 16-22
May 30-june 5
June 13-19
June 27-july 3
September 12-18
September 26 –October 2
October 1-16
October 24 – 30


La pieve di Palazzo Massaini

The old farmhouse, carefully restored into a farmhouse, offers you an infinity pool overlooking the surrounding countryside, a private garden and common areas where you can host parties and events.

La pieve di Palazzo Massaini

A place with a surreal atmosphere, where the rustic style of the ancient sandstone structure and the modernity of current technologies will make your stay a unique experience in authentic Tuscan style

La pieve di Palazzo Massaini

Far away from the noisy city life and surrounding villages, every corner of the estate offers wonderful panoramic views and enchanting atmospheres, giving a unique feeling of peace and serenity

La pieve di Palazzo Massaini

Just 500 meters from Palazzo Massaini

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