Tuscan San Gimignano & Siena
Medieval towers in the morning light, Vernaccia and a long lunch among the vines, and Siena's great shell-shaped piazza to end the day.
Two of Tuscany's most beautiful towns, joined by a quiet family estate where time slows down.
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
- 🗼 San Gimignano's medieval towers, the 'Manhattan of Tuscany'
- 🏛️ Siena's Piazza del Campo, home of the Palio
- 🍷 Vernaccia tasting and lunch at a family estate
- 🚶 A relaxed pace: two towns, not a checklist
Your Day
San Gimignano
A walk through the towers and the medieval center.
Vernaccia estate & lunch
A guided tasting of Vernaccia di San Gimignano at a family winery, followed by lunch at the estate.
Siena
Free time in Piazza del Campo and the historic center.
Good to Know
⏱️Duration & group size
Duration: 9 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
- Vernaccia tasting and lunch at the estate
- A guide who calls these hills home, fluent in English
- Tips and gratuities
💶Prices
Private tour, price per person by group size:
Pickups more than 30 minutes outside Florence may incur a supplement.
↩️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 is Vernaccia di San Gimignano?
One of Italy's oldest white wine appellations: crisp, mineral, and grown only around San Gimignano's towers.
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: lunch is served at the Vernaccia estate, paired with the wines you taste there.
How much walking is involved?
Both towns are explored on foot, over cobblestones and gentle slopes: comfortable shoes are essential.
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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