Tuscan Chianti Hidden Gems
Chianti as the people who make it live it: small family cellars, growers pouring their own wine, and nothing staged.
We leave the famous names to the coaches and follow the white roads to organic, multigenerational estates, where a tasting becomes a conversation and lunch is served among the barrels, often cooked by the winemaker himself.
Private tour, the whole day just for your group. The more you are, the less each person pays.
✓ Reserve with a 30% deposit · ✓ Free cancellation up to 48 hours before · ✓ Balance on the day
The Experience
- 🍇 Organic, single-family cellars in the heart of Chianti Classico
- 🤝 Tastings led by the growers themselves, never a rehearsed script
- 🍝 Lunch in the cellar, half or full day: handmade pasta and local produce, often cooked by the winemaker
- 🌄 White roads, olive groves and hilltop views from one estate to the next
Your Day
First estate
A walk through the vineyard and cellar, then a guided tasting alongside the grower.
Second estate: lunch with wine pairing
Here the tasting is the lunch: a long table in the cellar, each course of handmade pasta and the best local produce served with the estate's wines chosen to match it, often cooked by the winemaker.
Third estate (full day)
A smaller producer further into the hills, reached only on the full-day tour.
Good to Know
⏱️Duration & group size
Duration: 4–8 hours. Group: 2–8 guests. Guide: a local guide, fluent in English.
🚐Pick-up & drop-off
We collect you at your hotel or apartment in Florence. Where your street falls inside the ZTL limited traffic zone, we will agree on the nearest convenient spot in advance.
✅What's included
- Private door-to-door transport from your hotel in Florence
- All tastings at the wineries
- Lunch in the cellar, half or full day: handmade pasta and local produce
- English-speaking local guide
- Tips and gratuities
- Additional wine purchases
💶Prices
Private tour, price per person by group size:
Pickups more than 30 minutes outside Florence may incur a supplement.
🍇The estates we visit
Small, single-family cellars, handpicked across Chianti Classico. Each stop unfolds the same way: a walk among the vines, a glance inside the cellar, and a tasting led not by a script, but by whoever actually coaxed the wine into the bottle.
↩️Booking & cancellation
To book: a 30% deposit, paid online by card through a secure SumUp payment link we send you by email or WhatsApp. The balance is paid on the day of the tour, by card or contactless (every van carries a card reader) or in cash.
What's the black rooster on Chianti Classico bottles?
It's the Gallo Nero, the historic seal of the Chianti Classico Consortium. It marks wine made under the appellation's stricter rules. You'll see it on the neck of every authentic bottle.
How do we get there?
We collect you at your hotel or apartment in Florence and bring you back at the end of the day.
Is lunch included?
Yes, on both the half and the full day: lunch is served in the cellar of one of the estates, with handmade pasta and local produce, often cooked by the winemaker himself.
Dietary requirements?
Vegetarian, vegan, gluten-free: tell us when you book and we will arrange it with our hosts.
Can we ship wine home?
Most estates ship abroad, including to the US. Purchases are paid directly to the producer.
Check availability
Bookings open in January 2027. Send us your date and group size now: we reply personally with availability, usually within 24 hours.
Meet Andrea & Lorenzo
Your guides: Andrea, a WSET-trained sommelier who spent years working the land as an agricultural technician, and Lorenzo, who brings years of experience leading tours, a love for experiences that are real rather than staged, and the warm, accommodating way of reshaping the day around his guests that they mention in their reviews. Every route on this site is one we've driven, walked, or eaten our way through ourselves.
Your guide, in his guests' words
Written by guests of Andrea's earlier tours, before Tuscan Detour opened, and published on Google and TripAdvisor. Quoted as written, with surnames shortened and omissions marked […].
“A beautiful tour through some of the most enchanting wineries we have ever visited. Andrea made the entire day truly special […] it was an experience we will always treasure.”
“Andrea truly is an exceptional guide: knowledgeable, welcoming, attentive, and genuinely passionate about sharing the best of the region. His enthusiasm made the whole experience feel special, memorable, and far more than just a tour.”
“A special thank you to our guide, Andrea, who made everyone feel comfortable from the very beginning. He was extremely knowledgeable about wine and the local area, and a real pleasure to listen to throughout the day.”
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