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.
Food & Wine Journey in Tuscany — by Bike
An active culinary tour combining daily rides with cooking and wine experiences.
- Hands-on cooking classes with Chef Paolo
- Ride to wine tastings in Montalcino (Brunello focus)
- Welcome tasting of local cheeses and extra virgin olive oil
- Tuscan trattoria / osteria / one special dinner
- Val d’Orcia UNESCO landscapes + hill towns (Pienza, Montalcino, Siena area)
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.
2026 departure
May 8-14 CONFIRMED
May 22-28 SOLD OUT
June 5-11 CONFIRMED
June 12 –18 CONFIRMED
September 4 – 10 SOLD OUT
September 18 – 24 SOLD OUT
October 2 – 8 SOLD OUT
October 16 – 22 CONFIRMED
bikes available for this tour
Before You Book
Is this tour guided?
Yes. This is a guided Tuscany tour with an experienced guide and support throughout the week.
Where do we stay during the week?
You’ll be based in one private villa in Val d’Orcia for six nights—an ideal hub for loop rides and relaxed evenings together.
How many cooking classes and tastings are included?
Included are two hands-on cooking classes, a wine tour, and a cheese tasting—plus dinners and lunches as listed in the “What’s included” section.
Which wines will we taste?
Expect a strong focus on Brunello di Montalcino, plus other Tuscan classics (such as Nobile di Montepulciano, Chianti Classico, Orcia DOC, and Vin Santo) depending on the program.
What bikes are available for this tour?
Bike options vary by tour and include e-bikes, gravel, hybrid, e-gravel and road bikes. We’ll help you choose the best match for your route and riding style.
At a glance
Day 1 — Friday: Welcome to Val d’Orcia
Meet at Chiusi train station at 14:00; private van transfer to the villa; short bike test ride; meet Chef Paolo; cheese and olive oil tasting & welcome dinner.
Day 2 — Saturday: Montalcino & the Art of Brunello
Cycling journey through Sangiovese grape landscapes; visit Montalcino and its Enoteca; downhill ride to Castelnuovo dell’Abate; wine tour and lunch at Tenuta Fanti Winery.
- Dinner at 13 Gobbi in Montefollonico.
- Elevation loss: -817 m / -2680 ft
Day 3 — Sunday: Charming Pienza
Visit Pienza; ride through villages like Castelmuzio and Montisi; first cooking lesson with Paolo followed by dinner at the villa.
- Elevation loss: -764 m / -2503 ft
Day 4 — Monday: Le Crete & Monte Oliveto Abbey
Cycle through the Le Crete area and visit the Benedictine abbey with its frescoed cloister. Back to the villa for the pizza party.
- Elevation loss: -1338 m / -4389 ft
Day 5 — Tuesday: Monticchiello & Bagno Vignoni
Gravel experience, picnic lunch and spa day at thermal waters; dinner at La Terrazza del Chiostro.
- Elevation loss: -529 m / -1735 ft
Day 6 — Wednesday: Radicofani & the Legend of Ghino di Tacco
Cycle to Radicofani; visit the fortress and old town; cooking lesson with Paolo and farewell dinner at the villa.
- Main loop elevation loss: -1007 m / -3303 ft
- Longer loop option: 71 km / 44 mi · +1147 m / +3763 ft · -1147 m / -3763 ft
Day 7 — Thursday: Arrivederci!
Private transfer to Chiusi train station around 9:30.
DAY 1
Meet at Chiusi train station (a major stop on all the Rome-Florence lines) at 14:00
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: 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: 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
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 62 km | 38 mi elevation gain +1338 m | +4389ft / elevation loss -1338 m | – 4389 ft
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 9:30
On request we will arrange transfer at different time.
INFO TOUR
best period spring and fall
DIFFICULTY easy to medium
TOUR REVIEWS
Price & Inclusions
Cost: € 3600 per person in double occupancy | Single room supplement € 790
What’s included
- Six nights in private villa;
- Six dinners & Two lunches;
- Two cooking classes;
- One wine tour;
- One cheese tasting;
- All maps, trip notes and GPX 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 | Gravel, E-Bike € 260 | E-Gravel € 350
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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