Is lunch included in the base price?

No, the EUR 587 price covers the private tour, driver-guide commentary, and vehicle. A traditional full lunch at an organic farm or winery is an optional upgrade—request at booking.

Can we do wine tasting without lunch?

Yes. The tour includes an option to taste Craft Chianti Classico at a local vineyard. You can add this standalone without the full lunch upgrade.

What's included in pick-up and drop-off?

Hotel or private address collection in Florence at the start, and return to the same location at the end of the tour. Confirm your accommodation or meeting point when booking.

How many people can join, and can we mix groups?

The tour is fully private for your group only, up to a maximum of 6 travellers. No strangers are added; it's exclusively yours.

Do I need to book winery or lunch in advance?

It's recommended, especially in peak season (April–May, September–October). Inform the operator of your preferences at booking so they can reserve your spots and tailor the itinerary.

Is the tour suitable for people with mobility issues?

Siena and San Gimignano involve steep medieval cobblestone streets and stairs. The tour itself is flexible, but walking through these towns requires moderate fitness. Discuss any accessibility needs with the operator before booking.

Wine Tasting at winery Brogioni Maurizio

PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence 4

Lunch and Wine tasting in Organic farm Tenuta Casanova

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PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

(5)

Siena, Italy

Bus & Minivan ToursCultural ToursFood & Drink Tours

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About this activity

A private 8.5-hour Tuscan escape from Florence combining three iconic destinations: the art-filled medieval hilltop town of Siena, the tower-studded UNESCO village of San Gimignano, and the rolling Chianti Classico wine region. Your own driver-guide provides personalised commentary and flexibility to explore at your pace, with optional farm-to-table lunch and vineyard tastings included.

• EXPERIENCE FOR YOUR PRIVATE GROUP •

Enjoy an exclusive 8–9 hour private tour of Tuscany from Florence with a professional local driver-guide. Travel through the scenic Chianti wine region and explore the medieval gems of Siena and San Gimignano.

Visit iconic sites such as Piazza del Campo in Siena, famous for the Palio horse race, stroll among the medieval towers of San Gimignano (UNESCO site), and soak in the authentic atmosphere of the Tuscan countryside.

Upgrade your experience with an optional traditional Full Lunch at a local organic farm or winery, for a truly authentic taste of Tuscany.

8/9-hr Full-Day private tour of Tuscany
Private tour for a maximum of 6 travelers (your party only)
Visit the medieval cities of Monteriggioni, San Gimignano and Siena
Hear live commentary of the winery by your driver/guide
Taste Craft Chianti Classico wine at a local vineyard (option)
Hotel or private address pick-up & drop-off

Perfect for couples, families, and small groups looking for a relaxed, authentic, and fully private Tuscany experience.

Highlights

✓Explore Piazza del Campo in Siena, heart of the famous Palio horse race
✓Walk among San Gimignano's 14 medieval towers—a UNESCO World Heritage site
✓Drive through scenic Chianti Classico vineyards with expert local commentary
✓Optional Craft Chianti Classico wine tasting at a working vineyard
✓Upgrade to traditional lunch at an organic farm or winery
✓Private tour for up to 6 guests—no crowded group dynamics

Insider tips

★Book the lunch upgrade for an authentic agriturismo experience; vineyard meals often feature seasonal local produce and pair perfectly with estate wines
★Arrive early in Siena to beat day-trippers; your private timing lets you explore the Duomo and narrower side streets before crowds peak
★Wear comfortable walking shoes—Siena and San Gimignano are built on steep medieval streets with cobblestones
★Request your driver-guide suggest the best photo spots; locals know light timing and quiet vantage points tourists miss

Good to know

•Hotel or private address pick-up and drop-off included from Florence
•Maximum 6 travellers per tour ensures intimacy and flexibility to adjust the itinerary
•Monteriggioni stop included—a smaller, less-crowded walled village perfect for photos and a short stretch
•Comfortable private vehicle with air-conditioning; bring sunscreen, hat, and water for summer visits

Who it's for

Couples seeking a romantic, car-free Tuscan day with wine and sceneryFamilies and small groups wanting privacy and flexible pacing over rigid schedulesFood and wine enthusiasts aiming to taste authentic Chianti and regional cuisineCultural travellers focused on medieval Italian art, architecture, and UNESCO sites

Best time to visit

April–May and September–October offer ideal weather for walking medieval streets and vineyard visits without summer heat. Visit Siena between July–August only if you time around noon crowds; avoid mid-August (many locals close shops for holiday). Late afternoon light in San Gimignano is spectacular for photography.

Frequently asked questions

Reviews

(5)

David R.

Jun 2026

our guide Hana couldnt do enough for us and the bit at the end nobody expects was the highlight, and blew our Dubrovnik one out of the water.

Tom V.

Jun 2026

loved it — guide Amani top notch, blew our Crete one out of the water

James B.

Mar 2026

a stop the guide added on the fly ok but rushed, would only really suit you if youre not fussy, 6 stops in about 3 hours, tbh

John D.

Feb 2026

Amani our guide very good, and a stop the guide added on the fly we love it. Is much better than the tour we do in Paris before. We are very happy, recommend to all!

Rob P.

Jul 2025

our guide Kemal really knew their stuff and the bit at the end nobody expects was the highlight, and went last tuesday.

from€587/ person

4.8 · 66 reviews on Trustpilot

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