from
$120
From Florence: Tuscany Day Trip with Siena, San Gimignano & Winery Lunch
Relax on this Tuscan day trip with a 3-course lunch and 6 wine tastings
What's included
Expert, English-speaking guide
Round-trip transport
Guided winery tour in Chianti
Tasting of 6 wines
Traditional 3-course Tuscan lunch
Artisanal olive oil and balsamic tasting
Guide tips
Siena Cathedral entry ticket
Itinerary
Your tour begins in central Florence
Meet your tour leader in central Florence (look for the exact location on your booking voucher). Here, you’ll board a comfortable, air-conditioned vehicle and embark on a scenic journey through Italy's most famous food and wine region.
Historic Siena
Your first stop is the beautiful city of Siena, home to the famous Palio horse race held in the central Piazza del Campo since the Middle Ages. You'll explore this iconic square and see the world's oldest bank with your guide. Afterward, enjoy free time to wander the city and visit the stunning Siena Cathedral.
Chianti winery tour and tasting
Next, visit a family-run winery that has perfected Tuscan wine for 13 generations. You'll tour their vineyards, wine cellar, and fermentation areas before enjoying a curated tasting of six wines, including Vernaccia di San Gimignano DOCG, Rosé, Chianti, Super Tuscan Riserva, and Morellino di Scansano, paired with artisanal olive oils and Gold Reserve balsamic vinegar.
Traditional Tuscan lunch
Savor a three-course feast featuring Tuscan cheeses, cured meats, bruschetta, and salad, followed by Lasagne al Tartufo and hearty ribollita. Finish with cantucci paired with Vin Santo for a true taste of Tuscany's culinary heritage.
Medieval San Gimignano
After lunch, explore San Gimignano, a UNESCO World Heritage site nicknamed "Medieval Manhattan" for its iconic tower skyline. You'll have free time to wander inside the city walls and discover this fairy-tale town.
Your tour finishes in central Florence
After a wonderful day exploring historic Tuscan cities and savoring the region's food and wine, relax as your driver takes you back to Florence. The exact ending point can be found on your booking voucher.
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 24 hours in advance!
Mon, 07 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:
Dress Code: Comfortable walking shoes are essential for exploring the medieval towns and vineyards.
Accessibility: Unfortunately, this tour is not wheelchair accessible due to the vehicle specifications and uneven terrain.
Dietary Restrictions: This tour includes a traditional 3-course Tuscan lunch with wine; please contact us with any dietary needs in advance so we can do our best to accommodate.
Alcohol Consumption: This tour includes wine tastings; participants consuming alcohol should be of legal drinking age in Italy (18).
Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can enter sites on time.
Your 9-hour day trip from Florence includes:
English-speaking tour leader for the day
Round-trip transportation from Florence in a climate-controlled vehicle
Visit Siena with free time to visit the cathedral (on your own)
Wine tour and tasting at a traditional, family-run winery in Chianti
Taste 6 different wines
Traditional 3-course Tuscan lunch
Visit the medieval town of San Gimignano
What to bring:
Comfortable walking shoes
Water bottle
Sunscreen (in the summertime)
Government-issued ID (if you plan to partake in alcohol)