Day Trips from Pisa to Siena

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Chianti Classico Wine Tour and San Gimignano Visit Half Day

Tuscany... What Else? Discover the Magic of Chianti & San Gimignano! Leave the chaos of the city behind and immerse yourself in the timeless charm of the Tuscan countryside. Spend half a day among rolling hills, vineyards, and medieval villages — exploring the flavors, stories, and landscapes that make Tuscany one of the most beloved destinations in the world. -Wine Tasting Experience: Visit a welcoming family-run winery, where you’ll enjoy a tasting of five exceptional Tuscan wines, including the iconic Chianti Classico, the prestigious Super Tuscan, and the elegant Vernaccia di San Gimignano. Learn the basics of winemaking, uncover centuries-old traditions, and hear the legend of the Black Rooster, symbol of the Chianti. -Visit to San Gimignano: Continue to the medieval village of San Gimignano, a true open-air museum. Stroll through its narrow cobbled streets, admire the famous towers, and browse traditional shops and artisan boutiques that still preserve the charm of bygone times.

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Chianti Classico Wine Tour and San Gimignano Visit Half Day

5 hoursFree Cancellation

5.0

(1)

from $201

Price varies by group size

"Ramble Through The Rolling Hills Of Chianti" with lunch & Wine Tastings

Spend a day in the iconic landscape of the "Hills of Chianti" with a private tour. Pass between avenues of cypress trees, vineyards, sunflowers and medieval villages. Visit the historic village of San Gimignano and admire its ancient towers, enjoy homemade pasta and savor the best wines of the Tuscan countryside in a typical farm. Itinerary: • Our driver will pick you up at your location and take you on a journey through the rolling hills of Tuscany. We will move among olive groves, cypress trees and vineyards until we see the magnificent towers of San Gimignano. San Gimignano is also famous for the white wine Vernaccia, produced from the ancient Vernaccia vine. • Later we will move to a typical Tuscan family-run farm, to understand the secrets of wine production and enjoy a lunch with homemade pasta, bruschetta, percorino cheese and 6 wine tastings. • On the way back we will stop in a second typical cellar for a second tasting of Chianti, Sangiovese, Super Tuscan and more...

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"Ramble Through The Rolling Hills Of Chianti" with lunch & Wine Tastings

8 hoursFree Cancellation

5.0

(4)

from $296

Price varies by group size

San Gimignano view (Original photo of our tours)

Experience the best of Chianti from its historic hill towns and rolling landscape to its storied wineries in a single day with this private driving tour. Save hours with a dedicated driver, leaving you time to fit in visits to both San Gimignano and Monteriggioni. Break up your sightseeing with a wine-tasting lunch at a Tuscan farm and cap off your day with a Chianti winery tour and tasting.

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PRIVATE TOUR "Sweet Hills of Chianti and San Gimignano" with Lunch & 2 Tastings

8 hoursFree Cancellation

5.0

(2)

from $296

Price varies by group size

Florence San Gimignano and Siena from Pisa with Free Photography

This tour offers a unique opportunity to explore three iconic Tuscan cities—Florence, San Gimignano, and Siena—in just one day from Pisa. Experience Florence's Renaissance charm at Piazza del Duomo and Ponte Vecchio, the medieval allure of San Gimignano's Piazza del Duomo and Torre Grossa, and the Gothic splendor of Siena's Piazza del Campo and Cathedral. Enjoy free photography for 30 minutes to capture your memories. With convenient transportation between cities and expertly planned stops, this tour maximizes your time while providing a rich cultural experience. It's a perfect blend of history, architecture, and breathtaking scenery, ideal for travelers seeking to see Tuscany's highlights in a single day

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Florence San Gimignano and Siena from Pisa with Free Photography

14 hoursFree Cancellation

from $1,167

Price varies by group size

Likely to Sell Out

Explore two charming Italian towns, Siena and San Gimignano—without having to rent a car or tackle public transport—on this full-day trip from Pisa. Travel through the picturesque Tuscan countryside to your first stop, San Gimignano, and enjoy free time to shop, eat, or explore. Continue to Siena—known for its well-preserved medieval architecture—and choose whether to wander historic streets, sample gelato (own expense), or visit one of its UNESCO World Heritage-listed monuments. End the day back in Pisa.

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From Pisa or Lucca: Siena and San Gimignano Small Group Tour

9 to 10 hoursFree Cancellation

4.7

(25)

from $171

Price varies by group size

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Book a day trip Pisa and travel through the heart of Tuscany to explore the medieval city of Siena. Guided tours compile the UNESCO-listed city’s top sights into a 1-day itinerary, including the Piazza del Campo and the Siena Cathedral, which houses artworks by Donatello, Bernini, and Michelangelo. Explore the contrade neighborhoods, browse local ceramic shops, and take in the many architectural wonders. Some excursions combine a trip to Siena with a stop in the Chianti wine region for a tasting. Excursions ensure effortless sightseeing by handling all travel and providing a structured route through the city’s top Gothic and Renaissance landmarks.

Day Trips from Pisa to Siena

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