Cycling & Cooking in Tuscany
Tuscan lifestyle bike tour
Welcome to this bike tour: a captivating fusion of great bikes rides, gravel experience, history, wine, and cuisine.
Prepare for an unforgettable journey through Tuscany, where we’ve blended the thrill of cycling with the art of culinary delight.
This immersive tour showcases not only the breathtaking landscapes but also the timeless traditions of the Tuscan kitchen
Return from your trip with actual know-how to create a Tuscan dinner back home—it’s the ultimate keepsake!
WOW Moments
- Val d’Orcia UNESCO Site: Naturalistic, Artistic, and Cultural Park by bike.
- Discover Pienza, a compact town whose central square, Piazza Pio II, was transformed into the perfect Renaissance city by Pope Pius II. Explore its impressive cathedral and Palazzo Piccolomini, an architectural marvel.
- Montalcino and Brunello Wine: Cycle through vineyards, discover the secrets of Montalcino’s red wines, his Etruscan and Romans roots and enjoy a wine tour and a delightful light lunch.
- Abbey of Sant’Antimo: a precious example of Romanesque monastic architecture. Wanted by Carlo Magno, this abbey has played a great role in the history of the area, being close to Francigena road.
- Cooking Classes: Join Chef Paolo of Gusto Evoluto, an expert in sustainable high-class tourism.
- Siena’s Gothic Splendor: Explore Siena’s medieval charm especially the iconic Piazza del Campo, home to the Palio horse race.
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.
You will explore gorgeous loop rides in the beautiful val d’Orcia, Unesco site since 2004: Pienza, Montalcino, San Quirico. Not-to-be-missed: le Crete Senesi a rolling sea of land & sightsee the gothic Siena town.
Each meal will be paired with a Tuscan wine: besides the must Brunello, Nobile and Chianti classico you will learn about and sip Morellino di Scansano, Orcia doc and Vin Santo
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?
Hybrid, gravel E-bike ALL YOU NEED IS CHOOSE
2025 departure
May 16-22 SOLD OUT
May 30- June 5 CONFIRMED
June 6 -12 CONFIRMED
June 21 – 27 CONFIRMED
September 12-18 SOLD OUT
September 26 –October 2 SOLD OUT
October 10-16 CONFIRMED
October 24 – 30 CONFIRMED
Day | 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; Meet chef Paolo cheese and olive oil tasting & 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 Winery. | Distance: 40 km / 25 Mi Elevation Gain: +698 m/ +2290 ft |
Day 3 – Sunday | Charming Pienza Visit to Pienza; Cycling through villages like Castelmuzio and Montisi; first cooking lesson with Paolo followed by dinner at the villa | Distance: 38 km /24 Mi Elevation Gain: +763 m/ + 2503 ft Elevation Loss: -764 m/ – 2503 ft |
Day 4 – Monday | Siena & Le Crete Departure from villa; Visit to San Quirico and Asciano; Cycling through Le Crete area; Arrival in Siena and Free time to explore. Bach to villa for the pizza party. | Distance: 47 km/ 29 Mi Elevation Gain: +672 m / +2204 ft Elevation Loss: -900 m / – 2952 ft |
Day 5 – Tuesday | Monticchiello & Bagno Vignoni . Today gravel experience, pic-nic lunch and spa day at Thermal waters; | Distance: 28 km /18 Mi Elevation Gain: +387 m / +1269 ft Elevation Loss: – 529 m / – 1735 ft |
Day 6 – Wednesday | Exploring Radicofani, the Legend of Ghino di Tacco Cycle to Radicofani; Visit to fortress and old town; cooking lesson with Paolo and farewell dinner at villa | Distance 54 km / 34 mi |
Day 7 – Thursday | Arrivederci al prossimo bike tour Transfer to Chiusi train station around 10:00/11:00 |
DAY 1
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 La Pieve di Massaini, your 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
At 18:00 ready for introduction total week and the chef Paolo will talk about the cooking lesson ad start with a cheese and olive oil tasting, followed by dinner at the villa.
Meals included: lunch & dinner
DAY 2
Saddle up for a 40 km cycling journey that takes you through landscapes reminiscent of a Renaissance painting. First half of the ride to get to Montalcino is 80 percent gravel. Pedal through San Giovese grapes, from sangue di Giove, and visit the city bearing its name.
Montalcino 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 piazzas and The fortress. A gentle downhill ride awaits as you head to Castelnuovo dell’Abate to visit the Abbey of Sant’Antimo.
Enjoy a wine tour and lunch at Tenuta Fanti winery before returning to La Pieve. Two options for this: riding back for a total of 48 miles, it is a challenging but also terrific and rewarding way back. Ball in your court.
Dinner at Montefollonico at 13 gobbi – speciality tonight is Pici cacio e pepe
Distance 40.0 km elevation gain +698 m / elevation loss -817 m
Meals included: breakfast, lunch & dinner
DAY 3
Venture out for a 38 km bike ride that includes a visit to Pienza, the epitome of Renaissance architecture 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 visit to the town and lunch on your own. Complete your journey with the last 4 km on gravel roads before returning to La Pieve.
Back to La Pieve and ready at 16:30 Ready for your first cooking session with Paolo. 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 dinner
Distance 38 km elevation gain +763 m / elevation loss -763
Meals included: breakfast & dinner
DAY 4
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.
Tonight Pizza party at villa! You can’t do a food & wine vacation in Italy without dedicating an evening to gourmet pizza Let’s sample a variety of delicious pizzas. Prepare to be surprised how great is the wine paired we selected.
Total Distance km 47 km elevation gain +672 m / elevation loss -900 m
Meals included: breakfast & dinner
DAY 5
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 gourmet pic-nic lunch 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.
Dinner at Podere il casale
Total Distance 28 km elevation gain +387 m / elevation loss -529 m
Meals included: breakfast, lunch & dinner
DAY 6
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. Stroll through Radicofani’s stately old town.
Ready for another cooking lesson with chef Paolo followed by the farewell dinner? All you need is appetite & an apron!
Distance 54 km elevation gain +877 m / elevation loss -1007 m
ore longer distance:
Distance 71 km elevation gain +1147 m / elevation loss -1147 m
Meals included: breakfast & dinner
DAY 7
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.
INFO TOUR
best period spring and fall
DIFFICULTY easy to medium
TOUR REVIEWS
Price & Inclusions
Price
Cost: € 3200 per person in double occupancy
Single room supplement € 690
Inclusions
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 € 190 | Road bike, gravel, E-Bike € 260
2025 departure calendar
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.
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
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
Just 500 meters from Palazzo Massaini
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Tour Reviews
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.
Warmly,
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!
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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