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
-
Expert English-speaking tour leader
-
Private vehicle transport from Florence
-
Guided Chianti winery tour
-
6 wine tastings and a 3-course Tuscan lunch
-
Free time in Siena and San Gimignano
-
Guide tips
-
Siena Cathedral entry ticket
Tour Itinerary
-
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
You might also like...
Free Cancellation Skip the Line
Ultimate St. Peter's Basilica Dome Climb and Tour
See Michelangelo's La Pietà up close and climb the dome for stunning views of Rome and the Vatican
Free Cancellation
Scenic Golf Cart Tour of Rome in a Small Group
Experience eight UNESCO World Heritage Sites in Rome by Golf Cart
Free Cancellation Guided Tour
La Scala Theatre and Museum Tour in Milan
Skip the line into the world-famous opera house and museum with a local guide
Free Cancellation Likely to Sell Out
Eiffel Tower Summit Tour with Seine River Cruise
Admire twinkling Paris at night from the best spots in the city and sip Champagne while cruising
New Tour Transportation Included
Pisa & Cinque Terre Day Trip From Florence
Explore the charming towns of Monterosso and Manarola, embark on a coastal hike, and tour Pisa
Free Cancellation Guided Tour
Chinatown Local Food Tour in San Francisco
Taste your way around Chinatown’s lively streets, markets, and hidden gems with a local foodie guid
Free Cancellation Likely to Sell Out
Champagne & Oysters Paris Food Tour
Savor 11 exquisite tastings, including a sit down meal and dessert, across 5 stops in Le Marais
Guided Tour Trusted Partner
Skip-the-Line Borghese Gallery and Gardens Small Group Tour
Admire Renaissance and Baroque art and stroll the Villa Borghese Gardens with an expert guide
Free Cancellation New Tour
Trastevere Market Tour and Pasta Making Class in Rome
Visit a local market and learn how to make fettuccine from scratch with unlimited wine!
Free Cancellation New Tour
Dinner and Cabaret Show at Paradis Latin in Paris
Enjoy a 3-course dinner with wine, champagne, and a vibrant performance at this historic venue
Free Cancellation Guided Tour
Florence Highlights Tour with David and Duomo Entry
See Michelangelo’s David, visit the Florence Duomo, and walk the city’s historic heart
Free Cancellation Skip the Line
Skip the Line Sagrada Familia Tour
Discover the stories and secrets behind Gaudi’s grand basilica with an expert tour guide
Private Tour Skip the Line
Catacombs Private Tour in Rome with Transportation
Experience the Catacombs, Capuchin Crypts, and Santa Maria in Cosmedin with a personal guide
Free Cancellation Skip the Line
The Quickest Direct Access Private Vatican Tour
Explore the Vatican on a shorter, tailored tour that includes the Sistine Chapel
Exclusive Access Private Tour
Private Colosseum Tour with Arena Floor
Stand where gladiators fought on the Colosseum floor, then explore the Roman Forum and Palatine Hill
Day Trip Trusted Partner
Dachau Concentration Camp Memorial Tour by Train from Munich
A moving journey of remembrance, reflection, and history
Free Cancellation Private Boat Private Tour
Venice Islands and Artisans Private Tour
Explore colorful streets and ancient trades in Murano and Burano with a private boat and local guide
Guided Tour Skip the Line
Statue of David Evening Tour
Skip the line to see Michelangelo's David on a later tour of the Accademia Gallery with fewer crowds
Free Cancellation Skip the Line
Complete Florence Duomo Tour with Dome Climb and Secret Terraces
View this charming city from the hidden terraces of Brunelleschi’s dome after touring the cathedral
Skip the Line Likely to Sell Out
Vatican Museums & Sistine Chapel Tickets
Skip the line and gain quicker access to the Vatican so you can explore at your leisure
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.
