from
$118
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
English-speaking tour leader
Round-trip transportation from Florence
Visit Siena with free time
Guided winery tour in Chianti
Taste 6 different wines
Traditional 3-course Tuscan lunch
Artisanal olive oil and balsamic tasting
Visit medieval San Gimignano
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.
Make a stop in 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 on your own.
Take a Chianti winery tour and enjoy a 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.
Indulge in a 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, almond biscotti, paired with Vin Santo dessert wine for a true taste of Tuscany's culinary heritage.
Explore 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, 21 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 on this tour. Please note that if you plan to visit Siena Cathedral during your free time, they do require both men and women to have their shoulders and knees covered for entry.
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.
Please Note: Car seats are available upon request which must be made at least 72 hours in advance.
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 day trip 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
Artisanal olive oil and balsamic tasting
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)
See what people are saying
4.94
292 Ratings
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Vijay P.
September 14, 2026
Michelle S.
September 07, 2026
Great tour! Winery lunch was amazing & visits to the towns were perfect. Thank you to our guide Frank (Frankgelica??)
Great day trip !
Andrew F.
September 05, 2026
Well worth doing, great combination of sight seeing and winery lunch !
Very well planned tour
Deepak M.
September 03, 2026
Our guide Fabi was extremely nice and accommodating. The tour was fantastic and covered everything they mentioned in the itinerary. The winery was really good with loads of good wines for tasting. So we came for the wine but ended up loving the olive oil and buying those! Highly recommend this!
Wonderful day spent touring Tuscany
Megan B.
September 03, 2026
Our tour guide, Francesca, was wonderful providing a great balance between education and free time. She was friendly, patient, and informative. My family of 4 thoroughly enjoyed our day & definitely have no regrets about booking this particular tour. Alessandro was a great driver for our group also.
Brittan C.
August 28, 2026
Nancy
Nancy C.
August 24, 2026
Our tour was fantastic, our tour guide, Scirin Agha was a lot of fun and very informative. The lunch and wine tasting was delicious. A very smooth and enjoyable day!
Incredible!
Renee D.
August 21, 2026
This tour was amazing! Lori was so knowledgeable and kind. She was informative and answered all of our questions, took photos for us, and made the entire experience fun! Alessandro our driver was great as well!
Great day!
Jaymi B.
August 16, 2026
We booked a wine and city tour with The Tour Guys this week while in Florence. The experience was relaxing and great!! Our tour guide, Scirin, was super sweet and informative about all the places we visited! My husband left a personal item on the shuttle and we reached out to customer service and they went above and beyond to get it back to us!! We were so impressed and will definitely book with them in the future!
Great tour of Tuscany - Siena, wine tasting, lunch, San Gimignano
BEVERLY G.
August 12, 2026
FIVE STARS! The whole package was delightful from the places we explored to the excellent driver and tour guide. Food, wine, beautiful Siena cathedral, charming shops, gelato magnifico on every corner, to the comfortable bus. A very good value.
Absolute blast
Ryan Z.
July 30, 2026
Our guide Shirin and our driver Alexander were great
Nicholas C.
July 26, 2026
Tiffany P.
July 22, 2026
Wonderful!
Carissa D.
July 14, 2026
Very enjoyable day trip through Tuscany
Jason H.
July 13, 2026
Our sons and we had a very enjoyable day trip through Tuscany. Shirin served as our guide and shared just the right amount of information while also allowing our group to rest between sites (which we appreciated, especially due to the high temperatures). Our tour bus was nice as well. Alessandro safely shuttled us across the countryside in comfort. We would recommend without hesitation and will join future Tour Guy tours based on this tour.
Heidi S.
July 08, 2026
Very fun day trip.
Gregory C.
July 04, 2026
We had a wonderful day trip with three different stops. Our tour guide was very knowledgeable. The bus was very comfortable and all stops that we made where memorable. The last stop to San Gimignano was beautiful with breath taking views.
Terrific One-Day Trip from Florence
John K.
June 27, 2026
We really enjoyed this excursion! Not too much time on the bus, and enough time at each stop to get a flavor of the town. Winery tasting and lunch was really well done. Highly recommend!
Great trip
Madhavi K.
June 25, 2026
We had a wonderful day trip from Florence to Siena and San Gimignano. The wine tastings and lunch at the vineyard were excellent, and our tour guide was very informative. We enjoyed visiting Siena Cathedral, exploring the beautiful towers of San Gimignano, and tasting some of the best gelato. There was also plenty of time for shopping and enjoying the charming atmosphere. A fantastic experience and highly recommended!
Tuscany Day Trip
Philip B.
June 18, 2026
This tour was fantastic! Would definitely do it again!
Tour guide Schirin to Tuscany
William G.
June 17, 2026
Schirin was an excellent tour guide and helped make our Tuscany day trip one of the highlights of our visit to Italy. She was knowledgeable, friendly, organized, and provided great recommendations at each stop along the way. We especially appreciated her approach to guiding the tour. Rather than overwhelming us with information, she gave us useful background on each destination, pointed out the highlights, suggested places to visit, and then allowed us enough free time to explore on our own. The small-group format and comfortable mini-bus made the experience much more enjoyable than traveling on a large tour bus. The medieval towns we visited were beautiful and full of character, and the Tuscany wine tasting was outstanding. The winery experience was well organized, the wines were excellent, and it was a wonderful way to experience the region. The only minor issue was that the tour took place on a Sunday. A few of the shops and attractions Sharon recommended were either closed or opened later than expected, which unfortunately prevented us from enjoying some of her suggestions. This was a relatively small inconvenience and may have been due to changing local business hours rather than anything within her control. Overall, Schirin did a fantastic job, and we would highly recommend both her and this tour to anyone looking to experience Tuscany and its charming medieval towns. The combination of beautiful scenery, great wine, a comfortable small-group experience, and an excellent guide made for a memorable day.
Michelle S.
June 16, 2026
Eric C.
June 08, 2026
Tuscan Day Trip from Florence
Laura T.
June 06, 2026
Simply Stellar ✨️
Mo A.
June 03, 2026
The tour was terrific, fun and insightful! Our tour leader Manny was magnificent. We left the trip fulfilled and smiling.