What's included in the EUR 787 price?

Private air-conditioned minivan transport, licensed guide for the Siena portion of the tour, Chianti Classico wine tasting at a local vineyard, and entry to the towns. Optional lunch at an organic farm or winery is available at an additional cost (arrange when booking).

Can the itinerary be adjusted for our group?

Yes—because this is a private tour for your party only (max 6 travelers), your guide can tailor the experience. Discuss preferences with the supplier when booking: wine-focused vs. history-focused, time spent in each location, and lunch preferences.

How much walking is involved?

Expect 2–3 km of cumulative walking across the three towns, mostly on uneven medieval cobblestones. While not strenuous, comfortable shoes with grip are essential. Siena and San Gimignano involve uphill sections; those with mobility concerns should confirm with the supplier before booking.

Is this tour wheelchair or stroller accessible?

Siena's Piazza del Campo and San Gimignano's old town centre have cobblestone streets and steep gradients that challenge wheelchairs. Contact the supplier directly to discuss specific accessibility needs; the Chianti vineyard section is more accessible.

What time do we return to Florence?

The tour is 8.5 hours long; you'll typically return to Florence by early evening. Confirm exact pickup and drop-off times with the supplier when booking, as they depend on your hotel location and specific itinerary.

Are beverages and snacks included besides the wine tasting?

Only the Chianti wine tasting is included. Water and light refreshments are not explicitly mentioned; bring water, especially in warmer months. Lunch (if added) includes food and wine pairings; otherwise, plan budget for meals at local restaurants.

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PRIVATE Full-Day GUIDED Tour: Siena, San Gimignano and Chianti

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Florence, Italy

Food & Drink ToursBus & Minivan ToursCultural Tours

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About this activity

A curated full-day private tour from Florence combining three of Tuscany's most iconic destinations: the medieval hilltop city of Siena, the vine-draped Chianti wine region, and the perfectly preserved towers of San Gimignano. Your own licensed guide and private air-conditioned minivan ensure an intimate, flexible experience tailored to your interests.

Start your morning with a guided tour of the enchanting city of Siena, accompanied by an expert licensed guide who will bring the city’s medieval streets, iconic Piazza del Campo, and stunning cathedral to life.

In the afternoon, explore the heart of the Chianti wine region, discovering both famous vineyards and charming family-owned wineries. Tour the cellars, meet the winemakers, and taste their exquisite wines and local specialties🍷✨

Finally, wander through the breathtaking medieval town of San Gimignano, renowned as one of Italy’s most beautiful historic villages.

Add an optional lunch at a local organic farm or winery, savoring traditional Tuscan dishes paired with exceptional wines 🌿🍝

9-hour full-day private tour of Tuscany from Florence
Private tour for a maximum of 6 travelers (your party only)
Licensed tour guide in Siena included
Visit the medieval cities of Siena, Monteriggioni and San Gimignano
Craft Chianti Classico wine tasting at a local vineyard
Private air-conditioned minivan for your group

Highlights

✓Guided walking tour of Siena's Piazza del Campo and Gothic cathedral with expert local guide
✓Chianti Classico vineyard visit with winemaker meeting and wine tasting
✓Medieval San Gimignano: 14 historic towers and narrow cobbled streets
✓Private minivan transport for up to 6 travelers (no shared groups)
✓Optional farm-to-table lunch with Tuscan specialties and wine pairing

Insider tips

★Visit Siena early in the morning before tour crowds arrive at the Piazza—your guide can advise on the best photography angles and quieter side streets
★Ask your guide to arrange the Chianti tasting at a smaller, family-run winery rather than a large tourist estate for more authentic interaction with winemakers
★Wear comfortable walking shoes with good grip; San Gimignano's cobblestone streets are steep and uneven, especially on rainy days

Good to know

•Tour duration is 8.5 hours; departs early morning from Florence (exact pickup time confirmed by supplier before booking)
•Private tour accommodates up to 6 people; smaller groups receive more personalized attention and flexibility to adjust itinerary
•Air-conditioned minivan included; guide is licensed and fluent for Siena segment
•Optional organic farm or winery lunch can be pre-arranged; confirm dietary requirements when booking
•Moderate walking required (2–3 km daily across three towns); not recommended for those with serious mobility issues without prior discussion with supplier

Who it's for

Wine enthusiasts and food lovers seeking hands-on Chianti vineyard experiencesFirst-time visitors to Tuscany wanting to see multiple UNESCO-caliber destinations in one dayGroups of friends or families (max 6) preferring privacy and customizable itineraries over large coach toursPhotographers and history buffs keen on medieval architecture and Siena's Renaissance art

Best time to visit

Visit April–May or September–October for mild weather, smaller crowds, and harvest season activity in the vineyards. Avoid July–August (peak heat and tourists) and winter months when some smaller wineries have reduced hours.

Frequently asked questions

Reviews

(3)

Zoe G.

Jan 2026

our guide Nadia had so many stories and the bit at the end nobody expects was the highlight, and ideal with kids (ours are 6 and 9), and came away with 200+ photos.

Chris N.

Sep 2025

our guide Marco sorted everything for us and a stop the guide added on the fly was the highlight, and fine even with my dodgy knee, and 6 stops in about 3 hours, 10/10

Mariam L.

Sep 2025

our guide Tariq was brilliant and the bit at the end nobody expects was the highlight ... Last day of the trip so it wasnt too busy. Honestly better than the tour we did in bali last year, and came away with 200+ photos. Would book again no question, 10/10

from€787/ person

4.8 · 66 reviews on Trustpilot

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