Tuscany Tour: Wine Tasting & Medieval Towns

Embark on an effortless Tuscany discovery tour from Florence. Experience the charm of Siena, indulge in a Chianti wine tasting, and explore the enchanting city of San Gimignano.

Duration: 9 hours
Cancellation: 24 hours
Highlights

Begin your Tuscan journey with a friendly greeting from your tour leader in Florence. The adventure starts with a picturesque 1.5-hour drive through the rolling hills and vineyards of Tuscany in our comfortable, air-conditioned vehicle, creating the perfect atmosphere for a memorable day. The first destination is the breathtaking city of Siena!…

What's Included
  • Local and fun, English-speaking trip leader
  • Enjoy a wine tasting, sampling 6 of the region’s finest wines.
  • Free time in the picturesque medieval town of San Gimignano
  • Guided tour of the cellar and vineyards at a family-run Chianti winery.
  • Explore charming Siena with free time to visit the Cathedral (ticket excluded)
  • Round-trip Transportation…
What's Not Included
  • Hotel pick up / drop off
  • Entry to the Siena Cathedral
  • Entrance fees to ticketed places in San Gimignano
  • Gratuities (optional)
Additional Information

Searching for a simple method to explore Tuscany from Florence? Keen on experiencing a famous Chianti vineyard and spectating the incredible views in San Gimignano? You’ve found the perfect tour!
With pickups and drop-offs arranged, and a trip guide by your side through your Tuscan exploration, you just need to relax, taste local wines, and get…

Location
Plaza de Montelungo
Piazzale Montelungo
Please arrive 15 minutes early to check in for your tour. From Santa Maria Novella Train Station, follow the signs toward Piazzale Montelungo (bus terminal area). Next to the Piccolo Ristoro kiosk. Look for our friendly staff in red, holding a bright red 'The Tour Guy' sign!
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(67 Ratings)
5 stars
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1 star
Cindy_t
Oct 3, 2025
Excellent tour - Our host, Ana, was wonderful. She was so friendly, answerd everyone s questions and did a great job maki g sure we all got on the bus at each stop. The driver was on time and did a great job getting us safely to and from our stops. Lunch at the winery was so good. I wish I would have choosen a longer tour as 9 hours went by quickly.
Review provided by Viator
Shelly_w
Sep 22, 2025
Great wine! Food and fun! - Fun, great food, wine selection and guides. I was very impressed with how seamless the day was. I highly recommend spending the day on this tour.
Review provided by Viator
Rajeev_n
Sep 16, 2025
A Tuscan Day Dream with Wine and Wonders - This tour perfectly blends stunning Siena and San Gimignano with a relaxing Chianti wine tasting. Our guide was knowledgeable and friendly, and the lunch at the vineyard was delicious. A fantastic way to soak in Tuscany’s highlights in one day!
Review provided by Viator
Sanjay_g
Sep 16, 2025
Tuscany’s Wonders with The Tour Guy - Our guide was genuinely passionate and knowledgeable, making Tuscany’s beauty and history come alive at every stop. The Tour Guy team organized a seamless and memorable day—highly recommended for unforgettable Italian charm!
Review provided by Viator
Digvijay_s
Sep 14, 2025
Unbeatable Day in Tuscany’s Heart - Exploring Siena, San Gimignano, and the Chianti wine region was simply magical. The wine tasting and local lunch were outstanding. Highly recommended for anyone wanting a real taste of Tuscany!!!
Review provided by Viator
Farha_c
Sep 13, 2025
Tuscan Tuscan Treasures and Tastes - This tour was the perfect way to experience Siena, San Gimignano, and the Chianti region. Delicious wines, scenic towns, and expert guidance made it truly unforgettable. Highly recommended!
Review provided by Viator
Sunil_k
Sep 12, 2025
Unforgettable Tuscany Adventure! - The Tour Guy made exploring Siena, San Gimignano, and Chianti truly spectacular. Highly recommend this tour for authentic wines, food, and scenery.
Review provided by Viator
Matthew_c
Sep 22, 2025
A nice day if you want to briefly see a bit of everything - This tour was fun, interesting, and worth it. I give it a 4 or 4.5 instead of full marks only because I think they should give more time in either Siena or San Gimignano and cut the other. On the one hand, it is super cool to see both, but on the other they're both pretty rushed. The tour guide, Anna, was amazing!
Review provided by Viator
Hester_n
Sep 21, 2025
Our tourguide Frederica... - Our tourguide Frederica was just perfect and so helpfull - really the best. The bus was very comfortable. We enjoy enough time in the 2 little towns. Was fun picking grapes. Food and wine was good. The salesman at the winery was just to much in trying to sell his wines. The feeling I am going home with ... it was not about the comfort of the guests - only about how many wine they can sell.
Review provided by Viator
Diane_c
Sep 13, 2025
Nice day out - Enjoyed the actual tour. The only negative was how pushy the wine maker was after having lunch to buy something.
Review provided by Viator
From $85
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).