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From the very first climb out of Greve in Chianti, the landscape opens around you: vineyards, olive groves, medieval stone walls half-hidden in the trees. The e-bike makes the hills disappear. The pace is yours. The stops are generous.
By the time the day is over, you will have ridden through a village that barely seems to belong to this century, stood inside one of the most layered monasteries in all of Tuscany, and eaten pasta cooked in Chianti Classico wine, poured from the same bottles you’ll taste minutes later, by the man who made them.
This is not a cycling tour with a wine stop at the end. It is a journey through Chianti — on a bike, through history, around a table — that happens to leave from the same place it arrives.
The tour departs at 9:00 am from Greve in Chianti and returns to the same point around 3:30 pm.
The day begins in the main square of Greve, a town built for trade that still carries the shape of its medieval market. From here, the climb to Montefioralle begins.
Montefioralle is the kind of place that stops you. A perfectly preserved walled village, circular in plan, with narrow stone lanes, arched doorways, and views over the valley that have barely changed in six centuries. One of the most beautiful villages in all of Tuscany and few people outside the region know it exists.
From Montefioralle, the route descends through vineyards toward one of the most extraordinary places in Chianti: Badia a Passignano, a Vallombrosa monastery founded in 950 AD.
The guided visit lasts 45 minutes and takes you through eleven centuries of layered history: the council chamber, the cloister, the Last Supper Fresco by Domenico Ghirlandaio painted in 1476; the same Ghirlandaio who would later teach Michelangelo.For nearly a thousand years the monastery witnessed the rise and fall of the Florentine Republic. For almost a century it was transformed into the private castle of a wealthy Polish aristocratic family. And somewhere in its margins, Galileo Galilei taught mathematics here, to students and monks, explaining how to grind lenses and build telescopes.
After the monastery, the route continues to a small family producer in the heart of the Chianti Classico zone. The owner pours four wines personally — DOC, DOCG, and estate selections — in bilingual commentary that sits somewhere between English and Florentine.
The centerpiece of the lunch: pasta cooked directly in Chianti Classico wine. It turns the color of the Chianti it absorbed. The scent alone justifies the visit.
Almost entirely downhill. After a day of history and food, this is exactly the right way to finish, the landscape unfolding slowly below. Back in Greve around 3:30 pm.
Curious people who want to experience Chianti at a pace that allows them to actually see it. The e-bike handles the hills. The guide handles the logistics. You handle the wine.
No previous cycling experience required. If you can ride a bike, you can do this. The e-bike adapts to you — not the other way around.
100% of guests have rated this experience 5 stars ★★★★★
Chianti is waiting.
Once you’ve seen it this way, it’s hard to go back to seeing it any other way.
Neither. The electric assistance makes the hills effortless — you always control the level. This tour was designed for curious travelers, not athletes. If you can ride a bike, you can do this. We provide a quick orientation at the start. We’ve had 25-year-olds riding alongside 70-year-olds, all arriving together.
Yes, a professional guide accompanies the group for the full day — managing logistics, leading the monastery visit, and riding with you without dictating the pace. Active cycling time is approximately 3–4 hours. The remaining time is the monastery visit, tasting, and lunch. The day never feels rushed.
All dietary needs are accommodated with advance notice — vegetarian, vegan, gluten-free, allergies. For families with children, we have specific solutions: please let us know at booking and we’ll tailor the day accordingly.
Yes. Let us know at the time of booking and we’ll arrange a transfer from Florence to Greve in Chianti and back.
What’s included
Not included: personal travel insurance, additional beverages, personal expenses.
| Start / End | Greve in Chianti (same point) |
| Departure | 9:00 am |
| Return | ~3:30 pm |
| Total distance | 21 km |
| Elevation gain | 500 m — fully supported by e-bike |
| Cycling time | Approx. 3–4 hours (total day: 6.5 hours) |
| Experience level | None required |
| Who it’s for | Couples, families, groups — all ages |
| Transfer from Florence | Available on request |
We create the perfect conditions for your UNFORGETTABLE holiday in Tuscany. Each tour is a mixture of 5 essences: adventure, art & history, nature, wellness, and food.
Our goal is to exceed your expectations. Respect for the environment, health & safety, quality and compliance with legal requirements are our main values.
© Tuscany Quintessence SRL
Via G. Romagnosi, 20 Firenze (FI)
P.IVA Num. 06863080484
Share Capital f.p. 15.000 euro
Company registered in Firenze – 661889
RC Insurance UNIPOL N° 1/72444/319/189121854
Insolvency and Bankruptcy guarantee fund REVO N° OX00020928
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