Exclusive Siena and San Gimignano Tour & Chianti Wine Experience

4.8
(17 reviews)

10 hours 30 minutes (approximately)
Offered in: English

Board a comfortable, fully-equipped GT coach and set off to discover the wonders of Tuscany.

The first stop of this small group tour will be the magnificent city of Siena. Here, accompanied by a local guide, you’ll have the opportunity to stroll through the charming streets of the city, admiring the stunning Piazza del Campo and the impressive Siena Cathedral.

No trip to Tuscany would be complete without a stop at a Chianti winery. Take a relaxing break during your tour and indulge in a tasting of some of the region's most iconic wines. Alongside the wine, you'll also enjoy a selection of delicious local products, allowing you to savor the authentic flavors of Tuscany.

End your journey exploring San Gimignano, known for its 14 medieval towers and breathtaking views of the Tuscan countryside. Wander through its charming streets and piazzas, taking in its well-preserved architecture.

A perfect blend of history, beauty, and wine, this tour offers an unforgettable taste of Tuscany!

What's Included

Expert English Only Tour Leader
Free time in San Gimignano
Roundtrip transportation by air-conditioned minibus or minivan with free wi-fi
1 Hour English Only Guided tour of Siena with an Expert Local Guide
Sampling of wines, extra-virgin olive oil and regional products
Visit of a typical Chianti Winery with wine tasting
VIP Small Group Tour up to 25 participants
Pick up and drop off
Gratuities

Meeting and pickup

Meeting point
Piazzale Montelungo

TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

End point
This activity ends back at the meeting point.

Itinerary

Duration: 10 hours 30 minutes (approximately)
  • 1
    Siena

    The adventure begins in Siena, a city celebrated for its medieval charm and rich cultural heritage. A local guide will take you through its narrow streets, unveiling centuries of history. Admire the iconic Piazza del Campo, one of Europe’s most renowned squares, famous for hosting the thrilling Palio horse race. Marvel at the stunning Siena Cathedral, a Gothic masterpiece adorned with intricate details, marble floors, and priceless works of art by masters like Michelangelo and Donatello. Experience the lively atmosphere of this historic city, a proud rival of Florence throughout history.

    3 hours Admission ticket free
  • 2
    Piazza Salimbeni

    Stroll through Piazza Salimbeni and admire the stunning architecture of the buildings surrounding the square. The iconic Palazzo Salimbeni stands as a symbol of the town’s financial history, offering a glimpse into Siena’s rich past while providing a peaceful and picturesque setting in the heart of the city.

    30 minutes Admission ticket free
  • 3
    Duomo di Siena

    Follow your guide and admire from the outside the outstanding Duomo di Siena The Duomo di Siena, or Siena Cathedral, is one of the most remarkable examples of Italian Gothic architecture. Dedicated to the Virgin Mary, it was constructed between the 12th and 14th centuries and stands as a symbol of Siena’s rich history and artistic legacy.

    30 minutes Admission ticket not included
  • 4

    Continue your amazing journew with a visit to a traditional winery in the Chianti region, where you’ll indulge in a guided wine tasting experience. Savor the rich flavors of Chianti Classico and other local varietals, perfectly paired with regional delicacies like pecorino cheese, cured meats, and bruschetta. Learn the secrets of winemaking, from grapevine to glass, and embrace the traditions and passion that define this celebrated wine region.

    2 hours Admission ticket free
  • 5
    San Gimignano

    Next, travel through the idyllic Tuscan countryside to reach San Gimignano, a hilltop town often called the "Medieval Manhattan" for its iconic skyline of 14 ancient towers. Explore Piazza della Cisterna and Piazza del Duomo, stroll along charming streets lined with artisan shops, and admire the town’s remarkably preserved medieval architecture. The stunning views of vineyards and olive groves stretching out to the horizon will leave you spellbound, making San Gimignano an unforgettable highlight of your day.

    2 hours Admission ticket free
  • 6
    Piazza Della Cisterna

    Make your way to Piazza della Cisterna, the heart of San Gimignano’s historic center, and savor the internationally acclaimed, award-winning gelato from Gelateria Dondoli.

    30 minutes Admission ticket free
  • 7
    Collegiata di Santa Maria Assunta - Duomo di San Gimignano

    Admire the Duomo of San Gimignano from the outside, with its impressive Romanesque facade and beautiful positioning in the heart of the town, offering a glimpse of its medieval charm and historical significance.

    30 minutes Admission ticket not included
  • 8
    Rocca of Montestaffoli

    Explore the Rocca di Montestaffoli, both from the outside and within, where you can appreciate its imposing structure and wander through its historic interior. From the top, enjoy breathtaking panoramic views of San Gimignano and the surrounding countryside, immersing yourself in the rich medieval heritage of the town.

    30 minutes Admission ticket free
  • 9
    Piazza del Campo

    Visit one of the most significant squares in the city of Siena and let yourself be captivated by the imposing "Torre del Mangia". Built between 1338 and 1348, it was designed to match the height of the Siena Cathedral's bell tower, symbolizing the harmony between religious and civic authority in the city.

    1 hour Admission ticket free

Additional info

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
Supplied by Ciao Florence Tours Srl

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Tags

Day Trips
Full-day Tours
Bus Tours
Cultural Tours
Historical Tours
Art Tours
Spring Break
New Product
Short term availability

Cancellation Policy

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

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Rating

4.8 Based on 17 17 reviews
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