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San Gimignano, Chianti, and Montalcino Day Trip from Siena
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San Gimignano, Chianti, and Montalcino Day Trip from Siena

5.0(5 reviews)
11 hour(s)
English (United Kingdom)
Siena, Italy

Free cancellation

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Explore San Gimignano’s medieval towers and charming historic center

Taste Vernaccia wine, Italy’s first renowned DOCG white

Discover Chianti vineyards with optional local Tuscan lunch

Sample Brunello wine surrounded by stunning Montalcino vineyards

Explore the Medieval Towers of San Gimignano and the Famous Vineyards of Montalcino


The journey begins in the territory of Siena with a visit to the historic town of San Gimignano, a UNESCO World Natural and Cultural Heritage site renowned for its iconic medieval towers. Guests have ample time to explore the charming historical center, which is filled with traditional artisan shops and ancient palazzos. This town is also the exclusive home of Vernaccia, a high-quality white wine that holds the distinction of being Italy's first DOCG wine.


After soaking in the atmosphere of San Gimignano, the tour moves to a scenic Chianti winery for a relaxing break. Here, participants can enjoy an optional lunch featuring local delicacies such as salami and artisanal cheeses, perfectly paired with a tasting of regional Chianti wines. This stop provides a wonderful opportunity to appreciate the agricultural beauty of the Tuscan landscape while sampling the products that have made this specific area a global culinary destination.


The afternoon is dedicated to the Val d’Orcia, a stunning region designated as a UNESCO World Heritage site since 2004. The route leads to the hilltop town of Montalcino, which overlooks vast expanses of Brunello vineyards. These rolling hills have contributed significantly to the area's international fame. The landscape here is truly breathtaking, offering panoramic views that capture the essence of the Tuscan countryside and its long-standing commitment to viticulture and land preservation.


The final highlight of the day is a visit to a local wine cellar in Montalcino to taste the world-renowned Brunello di Montalcino. As one of Italy's premier DOCG wines, it serves as the perfect conclusion to a day spent exploring the history and flavors of the region. This comprehensive tour offers a perfect blend of cultural discovery, historical sightseeing, and premium wine tasting, ensuring a memorable experience for every traveler visiting the heart of Tuscany.

What's Included
  • Pick up service from Siena
  • A minivan with air conditioning for up to eight people
  • Expert multilingual escorts
  • Drop off service
  • Wine tastings at two top wineries feature premium selections
What's Not Included
  • Gratuities
  • Optional typical lunch available
Price start from

$ 174.66

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Activity Provider: My Tour in Italy

Customer Reviews

5.0
Excellent
Based on 5 reviews
J
Jack L.Google
October 24, 2025

Niccoló was a wonderful guide for our Siena + San Gimignano tour. It was a very easy process to communicate with the company and arrived on time at our villa location on the day of the tour. We were very pleased with the service and experiences that were included with the tour and the Chianti lunch was fantastic. I highly recommend booking for your travels in Tuscany!

B
Billy Google
April 19, 2025

Me and my family spent a great day thanks to the daily tour in Val d’Orcia organised by Tours of Tuscany. Niccoló and the woman in the office were so kind. We had a difficulty with the reservation but Niccoló solved it immediately. We have never visited Val D’Orcia before so we were looking forward to visiting it! Our driver Vincienzo brang us in lovely spots for taking some photos. He thought us the sets of the Gladior film. He also told us some funny stories, legends and curiosities about the places we have visited (Montalcino, Pienza). He was very kind and professional! I suggest you to ask for him if you want to book a tour with this company. We have had a wonderful experience with him. The two wineries we have visited were so nice. The wine maker told us the story of that place and stay with us during the wine tasting. Food and wine were great 100%. I couldn’t have dreamed of a better experience!

J
Jesus M.Google
October 28, 2023

We had the pleasure of joining Niccoló's wine tour in the enchanting Montalcino region of Tuscany. It was an incredible experience, to say the least. Niccoló's extensive knowledge of the area's rich history and the captivating stories he shared about Tuscany truly deepened our appreciation for the region. The Brunello wines we tasted were nothing short of extraordinary, and his personal recommendations for local spots were the perfect finishing touch to our unforgettable Tuscan getaway. I cannot recommend this tour enough for anyone who wants to immerse themselves in the beauty and history of this stunning region.

Explore More San Gimignano, Chianti, and Montalcino Day Trip from Siena
Explore More San Gimignano, Chianti, and Montalcino Day Trip from Siena
Explore More San Gimignano, Chianti, and Montalcino Day Trip from Siena
Explore More San Gimignano, Chianti, and Montalcino Day Trip from Siena
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Day In a City

Explore More San Gimignano, Chianti, and Montalcino Day Trip from Siena

Discover the wonders of Siena, Italy with this unforgettable experience. We start with a visit to San Gimignano, a UNESCO site known for its towers, historic center, and Vernaccia wine, Italy's first DOCG white wine. Highlights of your tour include: Explore the UNESCO World Heritage city of a hundred towersDiscover Vernaccia's birthplace, Italy’s first DOCG white wine.Enjoy Tuscan cheese, cured meats, olive oil, and fine wines.Visit a Montalcino wine cellar and learn about its heritage.. This tour includes: Pick up service from SienaA minivan with air conditioning for up to 8 people.Expert multilingual escortsDrop off serviceWine tastings at two top wineries feature premium selections.. Our day begins with an exploration of the beautiful Siena countryside, starting with a visit to San Gimignano, the enchanting city of a hundred towers, a UNESCO World Heritage site. Known for its medieval charm, San Gimignano boasts narrow streets, local artisan shops, and centuries-old palaces, making it a true jewel of Tuscany. Your tour escort will provide valuable insights as you enjoy free ti. Duration: 11 hours . Book your San Gimignano, Chianti, and Montalcino Day Trip from Siena today and create memories that will last a lifetime!