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
Piazza del Duomo, 10
Piazza del Duomo
Please arrive 15 minutes early. Meet your guide outside of the Regione Toscana building located on Piazza del Duomo 10, 50122 Firenze, FI. Look for our friendly staff holding a bright red sign with ''The Tour Guy'' on it!
Cancellation Policy

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

Customer Ratings
4.9
(36 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Mshillbillyhog
Jul 16, 2025
Anna - Tuscan wine tour - Anna, our guide did a wonderful job of sharing information about the towns we visited and in coordinating our activity.
Review provided by Tripadvisor
Kileykhall
Jul 16, 2025
Great experience and lovely tour guide Anna. - Enjoyed our entire day. Anna very knowledgeable and fun tour guide. The winery was a great experience as were the two towns we visited!
Review provided by Tripadvisor
Rajshesh
Jul 13, 2025
Best experience - Very nicely organized. Frederica was excellent as the tour guide. Informative, witty and engaging. Wine tasting and lunch at the winery was the highlight of this trip though Siena and San Gimignano were worthy of the visit.
Review provided by Tripadvisor
K5127sqdorisb
Jul 13, 2025
Wonderful tour in Tuscany - We had a wonderful time on this tour. Our guide, Francesco, is very knowledgeable on the area. He gave us history as well as information on each place we visited; and then let us explore in our own. He gave us tips on what to see, what to avoid and where to find the best desserts!
Review provided by Tripadvisor
Lldl2025
Jul 13, 2025
Learned Chianti wine and small town history, super welcoming host, food matching is great. Enjoyed our journey. - Very timely arrangement and considerate guide. Francesco made everyone on the tour felt comfortable and happy. Bus is clean with air condition, drive safely.
Review provided by Tripadvisor
Jennae820
Jul 11, 2025
The perfect tour - Our guide was amazing. He was fun ajd informative. I loved the personal information about food and tips etc. I would recommend this tour to everyone.
Review provided by Tripadvisor
Northstar754534
Jul 8, 2025
Day trip in Tuscany from Florence. - Our tour guide Federika was so enthusiastic and informative. Our driver Riccardo did a great job getting us there and back. The whole tour was exactly what we wanted to see. The essence of Tuscany with a winery lunch and tasting, Sienna, and San Gimignano. Amazing scenery, delicious wine and a great, fun guide.
Review provided by Tripadvisor
Shaz365
Jul 4, 2025
Fantastic - Trip was fantastic. The wine, olive oil, balsamic vinegar tasting along with lunch at the winery was one of the best experiences I’ve had on any tour. Ricciardo and Federica were great and looked after us well.
Review provided by Tripadvisor
Lori
Jul 3, 2025
Unforgettable Day in Chianti – Perfectly Organized and Delightful! - Unforgettable Day in Chianti – Perfectly Organized and Delightful! What an incredible day! This Chianti wine and food tour was everything we hoped for and more. From start to finish, the logistics were smooth and well thought out, the bus was clean, comfortable, and punctual, and our driver was skilled and courteous, making the journey through the scenic Tuscan hills a real pleasure. Our guide was fantastic knowledgeable, friendly, and passionate about the region. She shared just the right amount of history and culture without ever overwhelming us. The stops in Siena and San Gimignano were well chosen, with a great balance of tastings and free time. The winery we visited was charming and welcoming, offering generous pours and delicious local bites to match. The food was a real highlight, fresh, authentic, and perfectly paired with the wines. This tour was a perfect mix of relaxation, learning, and indulgence. Highly recommended to anyone wanting to experience the heart and flavors of Chianti in one enjoyable day!
Review provided by Tripadvisor
Pamelabd8474ip
Jul 3, 2025
Awesome experience! - This tour was perfect scheduled, logistic was perfect and the guide well prepared! we have the chance to see the city from the Senna. I would book this tour again! Thank you for the magic experience
Review provided by Tripadvisor
From $85
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).