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1 / 10PRIVATE Full-Day GUIDED Tour: Siena, San Gimignano and Chianti
(3)
Florence, ItalyFood & 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
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From€787
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