Private Chianti Wine Tour from Florence with Siena and San Gimignano Visit
Explore medieval hill towns of Tuscany with 6 tastings and a 3-course lunch included
If you're short on time but want Tuscany done right, this private tour from Florence is your golden ticket. You’ll have your own tour leader, your own driver, and a day built around what matters to you. Start in Siena, where centuries-old palazzos frame a piazza still used for horse races. Drive through Chianti's hills to taste six wines over truffle lasagne and slow-cooked ribollita. Then pause in San Gimignano, where 14 stone towers rise above terracotta rooftops, before returning to Florence.
What You Get With This Tour
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Expert English-speaking tour leader
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Private vehicle transport from Florence
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Guided Chianti winery tour
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6 wine tastings and a 3-course Tuscan lunch
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Free time in Siena and San Gimignano
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Guide tips
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Siena Cathedral entry ticket
Tour Itinerary
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1
Meet your private driver at Piazzale Montelungo
Your day starts at Piazzale Montelungo in Florence, next to the Piccolo Ristoro kiosk. Meet your tour leader, hop into your private vehicle, and head south through Tuscany's cypress-lined roads. -
2
Explore Siena
Arrive in Siena, home to the twice-yearly Palio horse race that packs the shell-shaped Piazza del Campo with roaring crowds. Walk the sloping piazza and spot the tower that looms over medieval brick buildings. After, enjoy free time to visit the black-and-white striped cathedral on your own. -
3
Chianti winery tour and tasting
Drive into Chianti's vine-covered hills to meet a family that's made wine here for 13 generations. Walk the Sangiovese rows, peek into aging cellars, and taste six wines, including crisp Vernaccia and bold Super Tuscan Riserva, paired with artisanal olive oil. -
4
Tuscan 3-course lunch
Sit down to a traditional feast that starts with Tuscan cheeses, cured meats, and bruschetta. Next comes lasagne al tartufo and ribollita, the hearty bread-and-vegetable soup that's fed families here for centuries. Finish with cantucci dipped in sweet Vin Santo. -
5
Free time in San Gimignano
Continue to San Gimignano, nicknamed Medieval Manhattan for the 14 stone towers that once showed off rival families' wealth. You'll have free time to wander cobbled lanes and climb to viewpoints where towers frame the hills in every direction. -
6
Your tour finishes at Piazzale Montelungo
Return to Florence in the early evening, arriving back where your day began. You'll leave with photos of tower silhouettes, a palate shaped by six wines, and stories about the families who still make Tuscany taste like home.
Additional Information
Good to know:
Dress Code: Comfortable walking shoes are essential for exploring the medieval towns and vineyards.
Accessibility: As this is a private tour, the itinerary can be adjusted to be wheelchair or mobility accessible. Please contact us after making the booking to make the proper arrangements.
Please note: The itinerary of a private tour can be adjusted to your needs. Please reach out if you do not see a start time that fits for your party. We would be happy to check with our ticketing team to see if we can accommodate you.
Dietary Restrictions: Please contact us after booking with any special dietary restrictions or allergies, so we can do our best to accommodate you.
Alcohol Consumption: This tour includes wine tastings; participants consuming alcohol should be of legal drinking age in Italy (18). Please bring a government-issued ID if you plan to partake.
Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can depart on time.
Your 9-hour tour includes:
Expert English-speaking tour leader
Round-trip transportation from Florence
Guided winery tour at family-run Chianti estate
Tasting of 6 estate wines
Artisanal olive oil and balsamic vinegar tasting
Traditional 3-course Tuscan lunch
Free time in San Gimignano and Siena
Private group experience
What to bring:
Government-issued ID
Comfortable walking shoes
Camera
Water bottle
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Frequently Asked Questions
Is this tour family-friendly?
Yes, this is a private tour so the pace and content can be adjusted for families. Keep in mind that wine tastings are included, and children may find the winery portion less engaging. Participants consuming alcohol must be 18 or older in Italy.
What if I have concerns about my mobility on this tour?
Unfortunately, this tour is not wheelchair accessible due to vehicle specifications and uneven terrain at the medieval towns and winery. If you have specific mobility concerns, please reach out to us at support@thetourguy.com before booking to discuss options.
Can dietary restrictions be accommodated?
Yes, we can work with the winery to accommodate most dietary needs with advance notice. Please contact us at support@thetourguy.com after booking with your specific requirements so we can make the proper arrangements.
Is the Siena Cathedral included?
Entry to Siena Cathedral is not included in the tour price. You'll have free time to visit on your own during the Siena stop if you'd like. Tickets can be purchased on-site.
