from
$1,329
From Florence: Private Chianti Wine Tour with Siena and San Gimignano Stops
Visit 2 wineries for 12 wine tastings and a 3-course lunch, plus enjoy hotel pick-up
9 h
Max 7 Guests
What's included
Follow hilltop views to wine by the glass
Florence hotel pick-up and drop-off
San Gimignano and Siena free time
Entry to two wineries
Twelve wine tastings
Three-course Tuscan lunch
Olive oil and balsamic tasting
English-speaking tour leader
Private group experience
Guide tips
Siena Cathedral entry ticket
Itinerary
Your tour begins at your Florence hotel
Meet your tour leader in your hotel lobby and settle into comfortable transport reserved just for your party.
Wander the lanes of San Gimignano
Step into the medieval hill town known for its skyline of stone towers and honey-colored streets. Use your free time to browse artisan shops, climb for big-valley views, and pause for an espresso or gelato before you head back into the countryside.
Tour a winery in the San Gimignano countryside
Arrive at a delightful villa surrounded by rolling Tuscan hills for a guided tasting tour of 6 wines. Surrounded by vineyards, you’ll sample bold reds and fruity whites.
Drive through vineyard country toward lunch
With a private tour, the pace stays easy as you roll past patchwork fields, olive groves, and hilltop hamlets. Your tour leader points out the landscape and sets up the flavors you’re about to taste at the table.
Settle in for a three-course Tuscan 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.
Taste wines at a Chianti estate
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.
Stroll Siena’s Gothic streets and piazza
Arrive in Siena for free time to soak up its brick lanes and Gothic atmosphere. Walk to the landmark Piazza del Campo, then drift past cafés and small shops before meeting back up to depart.
Your tour ends at your preferred drop-off point in Florence
After Siena, relax on the ride back as the vineyards give way to Florence’s rooftops. Your driver drops you at your hotel or anywhere you’d like in the city.
For Reference Only. Itineraries are subject to change
Select participants and date
Start times are in the product’s local time
Free cancellation up to 7 hours in advance!
Tue, 01 Sep 2026
Meeting and drop-off point
Important Details
Discover what to expect, what's included, and everything you need to know before booking.
Good to know:
Hotel pick-up: Please include your accommodation details in the "additional info" section during checkout.
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 tour includes:
Expert English-speaking tour leader
Round-trip transportation from Florence
Visit and entry to two wineries
Tasting of 12 estate wines
Artisanal olive oil and balsamic vinegar tasting
Traditional three-course Tuscan lunch
Free time in San Gimignano and Siena
Private group experience
What to bring:
Valid ID
Comfortable walking shoes
Camera
Water bottle