from

$1,307

From Florence: Private Chianti Wine Tour with Siena and San Gimignano Stops

Private TourTransportation Included

Visit 2 wineries for 12 wine tastings and a 3-course lunch, plus enjoy hotel pick-up

Private TourTransportation Included

9 h

Max 7 Guests

Looking for a well-paced Tuscany tour without compromises? This is the tour is for you! After hotel pick-up in Florence, spend time in San Gimignano, a hilltop town of towers and sweeping countryside views. Next, visit two wineries for six tastings at each, with a three-course Tuscan lunch and olive oil and balsamic tasting breaking up the day. End exploring Siena’s gothic streets and landmark piazza, then return to Florence with drop-off anywhere in the city.

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!

Mon, 21 Sep 2026

Meeting and drop-off point

Pick-up is at your hotel in Florence. The day ends with drop-off at your hotel or anywhere you prefer in Florence.

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

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FAQs

Where to meet?

Pick-up is at your hotel in Florence. The day ends with drop-off at your hotel or anywhere you prefer in Florence.

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.

Do I need to be 18 to join the wine tastings?

Guests must be of legal drinking age in Italy (18) to participate in wine tastings. Bring a government-issued ID if you plan to partake.

Is hotel pick-up Included in this tour?

Yes, hotel pick up and drop off is included on this tour. Please include your accommodation details in the "additional info" section during checkout. Hotel pick up and drop off cannot be included if the proper information is not provided. If you need to change you accommodation info or you were not able to include it during checkout, please contact us so we can make the proper arrangements with our partners.