From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Tuscan Tastings

A day trip from Florence to Pisa, San Gimignano, and Siena is a scenic escape into Tuscany’s charm—think iconic landmarks, rolling vineyards, and medieval towns. You’ll snap photos at the Leaning Tower, savor local pourings over lunch, and wander cobbled streets rich with history.

Pisa

Embark on your Tuscany adventure starting with the iconic city of Pisa. As you step off the coach, be greeted by the mesmerizing Field of Miracles which includes the Cathedral, the Baptistery, and the world-famous Leaning Tower. Take the chance to snap creative photos alongside this 56-meter-tall structure with a 4-degree tilt. Or, lose yourself in the charm of local streets.

San Gimignano

From Pisa, drive to San Gimignano where a traditional Tuscan Lunch with wine pairing, (if the option is selected) will be served. After your meal, freely explore the 'Manhattan of the Middle Ages' nicknamed so for its iconic tall towers, creating a skyline reminiscent of a modern city.

Siena

The final destination is Siena, accessible via a scenic drive through the captivating Chianti countryside. Siena, a breathtaking hilltop town, boasts a wealth of art, traditions, and picturesque views.

From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Tuscan Tastings

Discover the enchanting landscapes and historic landmarks of Italy on this full-day tour from Florence to Pisa, San Gimignano, and Siena. This comprehensive sightseeing experience includes visits to the Leaning Tower of Pisa, the medieval towers of San Gimignano, the stunning cathedral in Siena, and a Tuscan lunch with wine tastings. The tour covers approximately 150 kilometers (93 miles) through the picturesque Chianti region and Tuscany, ensuring you have ample time to explore each destination. With dedicated multilingual assistance on board, this day trip is designed for groups of up to 45 people, offering a comfortable ride with plenty of photo opportunities along the way. The tour runs from morning until early evening, providing guests with an immersive experience that highlights the rich history and culture of Tuscany.

Explore the Leaning Tower of Pisa

Your tour stops at the Leaning Tower of Pisa where you will marvel at this iconic 56.7-meter (186 feet) tower, which has been tilting since its construction began in 1173. The tower is part of the larger complex known as the Square of Miracles or Piazza dei Miracoli, a UNESCO World Heritage site that also includes the Cathedral and Baptistery. Visitors can climb to the top for panoramic views of the city, but due to structural concerns, access has been limited since 1990 when restoration began; it reopened in 2001 after extensive work was completed. The tower is unique not only because of its tilt but also due to its intricate marble facade and Romanesque architectural style. Spend about an hour here exploring the square, taking photos, and learning about the history from your guide.

Admire San Gimignano's Medieval Towers

At San Gimignano, guests can explore a town famous for its 14 medieval towers standing among its historic walls. These towers were built in the 12th and 13th centuries as symbols of power and wealth by competing noble families; today, only seven remain intact from an original total of 72. The tallest tower is Torre Grossa, reaching a height of 54 meters (176 feet). Visitors can walk along the town's cobblestone streets and climb inside some towers for spectacular views over the rolling hills of Tuscany. Spend around two hours in San Gimignano enjoying its medieval charm, tasting local wines, and sampling traditional Tuscan cuisine at one of the many charming restaurants.

Discover Siena’s Medieval Squares

In Siena, guests can discover a city that has preserved much of its medieval architecture and character. The heart of Siena is Piazza del Campo, an oval-shaped piazza framed by palaces and arcades where the famous Palio horse race takes place twice each summer since 1656. Nearby, the impressive Cathedral of Santa Maria Assunta features Gothic architecture with a façade made from black and white marble that contrasts dramatically against the surrounding buildings. The cathedral was begun in 1259 and completed over several centuries; its interior houses numerous works of art including frescoes by masters such as Duccio di Buoninsegna and Simone Martini. Spend approximately three hours exploring Siena, with an optional guided tour to delve deeper into the city's history and significance.

Tour Highlights

• Round-trip transportation from Florence
• Stops at Pisa’s Leaning Tower, San Gimignano towers, and Siena cathedral
• Lunch in a historic Tuscan villa with wine tastings
• Dedicated multilingual assistance on board (English, Italian, Spanish)
• Photo opportunities along the way through Chianti region
• Comfortable ride for up to 45 people
• Access to medieval squares and landmarks including Piazza del Campo in Siena
• Guided tour option at Siena cathedral with historical insights

Perfect for history enthusiasts, architecture lovers, and foodies, this full-day tour from Florence provides an immersive experience of Tuscany’s rich cultural heritage. The day trip allows you to explore the Leaning Tower of Pisa, marvel at San Gimignano's medieval towers, and stroll through Siena’s historic squares, giving you a comprehensive understanding of Italy’s medieval history while enjoying traditional Tuscan cuisine and wine tastings.