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
  • Savor a traditional 3-course Tuscan lunch featuring local specialties
  • 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…
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

Seeking an easy way to explore Tuscany from Florence? Interested in visiting a famous Chianti winery and experiencing the stunning views in San Gimignano? Your perfect tour awaits!
With round-trip transportation and a tour leader guiding your Tuscan journey, simply relax, savor local wines, and let the region’s beauty captivate you.
The first stop of the…

Location
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
(80 Ratings)
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Kamlesh_b
Dec 29, 2025
A perfect day exploring - Everything went exactly as planned. The guide explained things clearly, kept the group engaged, and ensured we had plenty of time to enjoy.
Review provided by Viator
Digvijay_s
Dec 29, 2025
Friendly and Professional Service - The staff and guide were polite, helpful, and professional, creating a warm atmosphere that made the tour very pleasant.
Review provided by Viator
Vinay_p
Dec 18, 2025
Wine, Views, And Villages - Loved every stop on this itinerary. Walking the medieval lanes, then sitting down to a proper three‑course Tuscan meal with Chianti wines made the long day totally worth it and never felt rushed.
Review provided by Viator
Priyanshu_l
Nov 24, 2025
Family-Friendly Tuscan Adventure - Went with my parents and everyone enjoyed it. The guide kept the history light but interesting, the scenery between towns was stunning, and lunch at the winery catered well to different preferences at our table
Review provided by Viator
Prabhat_p
Nov 24, 2025
Tuscan Dream Day - This tour was the highlight of my Florence stay. The drive through Chianti, exploring Siena’s streets, and then wine tasting over a relaxed Tuscan lunch felt perfectly paced and really well organized.
Review provided by Viator
Sanjay_g
Nov 24, 2025
Perfect First Tuscany Trip - As a first‑time visitor, this was ideal. A guide explained Siena’s history, we got free time in San Gimignano, and the winery lunch with Chianti and local olive oil was absolutely unforgettable.
Review provided by Viator
Dishani_s
Nov 24, 2025
Stress-Free Countryside Escape😌 - Traveling solo, this took all the hassle out of seeing Tuscany. Comfortable coach, friendly escort, clear timing, and a charming family‑run winery where they walked us through each wine we tasted.♥️😍🥰
Review provided by Viator
Harsh_s
Nov 24, 2025
Unforgettable Paris Evening—Tower & River Magic - My partner and I booked this as a day trip from Florence and it felt so romantic. Siena’s cathedral area, San Gimignano’s towers, and sipping Chianti over vineyard views were exactly what we hoped for.
Review provided by Viator
Sunil_k
Nov 24, 2025
Memorable Guide And Winery - Our guide kept the group organized and shared useful tips without overtalking. The winery visit stood out: generous pours, clear explanations of Chianti, and a hearty Tuscan meal that felt authentic, not generic.
Review provided by Viator
Maps01926096549
Oct 31, 2025
Lori the best Tour Guide!! - Lori was amazing tour guide. Very sensitive to the needs of my friend who had problem keeping pace with other tourist. Also she sent my kindle to US ( California) which I forgot in my hotel room. She took trouble to DHL to California taking out time from her busy schedule! I recommend every tourist to take her as a tour guide to Sienna,wine tour and San Gimmignana!! Well done Lori! Love from Meetu and Gurmeet and Geve!!
Review provided by Tripadvisor
From $75
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).