Planning a day in Tuscany’s countryside can be tricky, with winding roads, remote villages, and countless wineries to choose from. With a 3-course lunch and 6 wine tastings, allow us to take the guesswork out of your Tuscan experience. Start in Florence, drive through Siena’s rolling hills, walk the medieval streets of San Gimignano, and tour a family-run Chianti winery. Along the way, learn the stories behind Chianti’s renowned wines and soak in the charm of Tuscany’s most stunning landscapes.
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.
For Reference Only. Itineraries are subject to change
Select participants and date
Free cancellation up to 24 hours in advance!
Thu, 18 Jun 2026
Meeting and drop-off point
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Important Details
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Tuscany Day Trip
Philip B.
Verified Review
June 18, 2026
This tour was fantastic! Would definitely do it again!
Tour guide Schirin to Tuscany
William G.
Verified Review
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.
Verified Review
June 16, 2026
Eric C.
Verified Review
June 08, 2026
Tuscan Day Trip from Florence
Laura T.
Verified Review
June 06, 2026
Simply Stellar ✨️
Mo A.
Verified Review
June 03, 2026
The tour was terrific, fun and insightful! Our tour leader Manny was magnificent. We left the trip fulfilled and smiling.
Tuscany Trip
Frederick G.
Verified Review
May 30, 2026
Really nice - the guide could have given more history of different areas , what the terrain was for the older people. The winery was very good wine and food - felt a little rushed - meal was great and wanted to visit the group and have time to drink wine . Thank you
Danielle Maur
Danielle M.
Verified Review
May 27, 2026
Wonderful tour!!! Lunch and wine tasting was beautiful and delicious. Tour guide was knowledgable and helpful.
A wonderful day spent in Tuscany
Lisa A.
Verified Review
May 25, 2026
This tour is wonderful, from the moment you step foot on the bus. We enjoyed our time in Sienna, then off to the winery for an amazing meal and wine tasting. Finishing up in the very charming San Gimignano was the perfect way to complete this tour.
Send Jim and Gino and pizza with wine and lunch
Judy J.
Verified Review
May 25, 2026
Victoria was amazing. She was very informative and helpful and the bus driver. Alessandro was also amazing.Simone at piggio ai laghi was also and we enjoyed our lunch. The meeting start point is hard to find,. He went with a group of six and gave ourselves an extra 25 minutes to find the meeting start point.
Ranee M.
Verified Review
May 24, 2026
Lori was awesome. Very informative and cute humor.
Fabulous Chianti region tour
Irene P.
Verified Review
May 18, 2026
Fabulous day trip from Florence, amazing wine and lunch, Frederica was very knowledgeable and a delight to spend the day with. Gave great info about the towns ambiance and history. Highly recommend Frederica for a perfect experience!
Tuscany tour
Linda Z.
Verified Review
May 09, 2026
Great tour with Frederica, highly recommend.
Our Taste of Tuscany
James T.
Verified Review
May 09, 2026
The tour was very nice. The right amount of time in each stop. Plenty of wine, cheese, meats, and the lunch was filling and tasty. The tour guide was outgoing and informative. Gimignano was the last stop, which included walking, and appeared to us to be a little out of order after filling up at lunch with eats and drinking. However, it was a nice tour and worth the trip.
Kara M.
Verified Review
May 07, 2026
Great day trip! Federica was amazing!
Fantastic tour!!! We had a blast
Kirk G.
Verified Review
May 06, 2026
Manny was an amazing tour guide, bus driver did an incredible job navigating the roads. Siena, Winery and San Gimignano were awesome destinations. We thoroughly enjoyed the day.
Awesome tour
Jeff L.
Verified Review
May 04, 2026
This was a wonderful tour, Fredrica was absolutely wonderful, she keep us well informed and everybody on schedule.
Linda C.
Verified Review
May 02, 2026
Enjoyed the tour; especially the winery. The lunch was delicious too! Wish there was more time in each town though but overall it was very enjoyable.
Joanna Matlak
Joanna M.
Verified Review
May 01, 2026
5-star trip because the tour guide is a 5-star guide, which we also experienced last year in our Firenze food trip.
Amazing!!
Lucca G.
Verified Review
April 30, 2026
My mother and I had a great time. The guide, Federica, was terrific and very sweet. Our driver was also great! The scenes were beautiful and the winery was fantastic. 5 stars all around.
Tuscany wine tour, Siena and San Gimigniano
Ricardo C.
Verified Review
April 25, 2026
Amazing experience to
Celebrate my 53rd birthday! Great time!!!
Paul S.
Verified Review
April 23, 2026
What a great tour.
Lovely to visit other beautiful cities in Tuscany .
Highlight was the wine tour I can swirl my wine like a professional now.
Particular mention to Frederica and Alessandro our tour guide and bus driver.
Fredrick for her information and friendliness.
Also the balance between giving just the right amount of information and allowing time for quite particularly welcome after the wine tour.
To Alessandro who got us everywhere on time which is no mean feat in Florence traffic.
Would recommend this tour
Jeff D.
Verified Review
April 15, 2026
This tour is a winner
Steven S.
Verified Review
April 12, 2026
We had so much fun on this tour and the pace was perfect. The tastings and lunch at the winery were fantastic. Our host there was very knowledgeable as well. Sienna and San Gimignano are beautiful towns that have amazing character and nice shops.
Mrs Callard
Zoe C.
Verified Review
March 31, 2026
Lori and Alessandro were incredible, their knowledge was wonderful, very kind and entertaining. We thoroughly enjoyed our tour. Thank you
