Tuscany Day Trip: Siena, San Gimignano & Pisa w/ Winery Lunch
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Overview
The Tuscany Day Trip from Florence lets travelers see the best of Tuscany in one day! This guided bus tour takes you from the Santa Maria Novella Train Station in Florence through the beautiful Tuscan countryside, visiting Siena, San Gimignano, and Pisa.
In Siena, explore historical places like Monte dei Paschi di Siena (one of the oldest banks), the Contrade of Siena, and the Piazza del Campo, where the famous Palio horse race takes place. Visit the Duomo of Siena, a beautiful cathedral filled with history and art. The tour then goes to Fattoria Poggio Alloro, where you can enjoy a tasty farmhouse lunch with vegetarian and gluten-free options, plus wine tasting of four different wines.
After lunch, the tour continues to San Gimignano, a charming medieval town known for its towers. Here, you can wander through the Piazza della Cisterna, the Piazza del Duomo, and La Rocca, soaking in the town's unique atmosphere. Finally, the tour heads to Pisa to see the Leaning Tower of Pisa, one of the world's most iconic landmarks. This full-day trip includes a professional English-speaking guide, transportation in an air-conditioned vehicle, and free time to explore each town. It's a great way to experience the highlights of Tuscany.What's included is wine tasting of four varieties, free time to explore the towns at your own pace, a hearty farmhouse lunch with veggie and gluten-free options, a professional English speaking tour guide with you for the whole day, a guided walking tour of Siena with entrance fee to the cathedral, and an air-conditioned vehicle.




Highlights
See Tuscany's Best: Visit Siena, San Gimignano, and Pisa in just one day!
Wine Tasting Included: Taste four different wines at a Tuscan winery.
Enjoy a Farmhouse Lunch: Eat a delicious Tuscan lunch with veggie and gluten-free choices.
Expert Guide: Learn about Tuscany from a friendly, English-speaking guide.
Sentiment Analysis
Customers generally enjoyed the Tuscany day trip, especially the chance to see many famous places and the tasty lunch with wine. Some felt rushed and wanted more free time at each stop.

Customers really liked seeing multiple cities in one day.
The lunch and wine tasting at the winery was a favorite.
Many found the tour guide to be knowledgeable and friendly.
The bus was comfy and made the trip easy.
Some people felt that there was not enough free time in each city.
A few customers wished they had more time at the Leaning Tower of Pisa.
The Journey
Santa Maria Novella Train Station, Florence
Your Tuscan escapade begins at the bustling Santa Maria Novella train station in Florence, a gateway to a world of Renaissance art and architectural marvels. As you gather near the taxi stand, anticipation fills the air for the adventures that lie ahead. This iconic station serves not just as a meeting point but as a launchpad into the heart of Tuscany, promising a day filled with exploration and discovery.
Siena
Step back in time as you enter Siena, a UNESCO World Heritage Site and a quintessential medieval hill town. Wander through its labyrinthine streets, where history whispers from every stone. A guided walking tour unveils treasures like the awe-inspiring Siena Cathedral, a masterpiece of Gothic architecture. Afterwards, immerse yourself in the Sienese lifestyle, indulging in local delicacies and soaking in the vibrant atmosphere of this timeless city.
Monte dei Paschi di Siena
Discover the roots of Siena's prosperity at Monte dei Paschi di Siena, the world's oldest surviving bank. Founded in 1472, this institution stands as a testament to Siena's historical significance as a financial hub along the Via Francigena pilgrim route. Learn how the city's wealth grew through banking and trade, shaping its cultural and architectural landscape. This historic site provides insight into the legacy of Siena, where finance and history intertwine.
Contrade of Siena
Delve into the unique cultural fabric of Siena by exploring its 17 'contrade,' or districts, each with its own symbol and identity. These ancient divisions ignite fierce rivalries, especially during the Palio horse race. Discover the self-contained worlds within each contrada, complete with their own churches and fountains, where newborns are baptized, highlighting the deep sense of belonging and tradition that defines Sienese life. Understanding the contrade provides a glimpse into the soul of Siena, where community and competition fuel the city's vibrant spirit.
Piazza del Campo
Experience the heart of Siena in Piazza del Campo, a breathtaking seashell-shaped square that serves as the city's gathering place. This unique piazza transforms into a thrilling racetrack twice a year for the Palio horse race, a 600-year-old tradition. Immerse yourself in the vibrant atmosphere as your guide brings the Palio to life, recounting the intense rivalries and passionate celebrations that define this unforgettable event. Whether you're sipping coffee or witnessing the Palio, Piazza del Campo captures the essence of Sienese life.
Duomo of Siena
Behold the Duomo of Siena, a jewel of Gothic architecture and a treasure trove of artistic masterpieces. Prepare to be amazed by the cathedral's unique floor, an intricate artwork crafted from precious marbles over two centuries. As you walk through the cathedral, immerse yourself in the grandeur of its interior and the artistry of its design. The Duomo of Siena stands as a testament to the city's artistic heritage, offering a visual feast for art enthusiasts and history buffs alike.
Fattoria Poggio Alloro
Indulge in a Tuscan culinary experience at Fattoria Poggio Alloro, an organic, family-run wine estate nestled amidst rolling hills. Enjoy an informal wine tasting lesson and savor a traditional Tuscan lunch with homemade pasta, cured meats, local cheeses, and biscotti, all paired with the estate's exquisite wines. This idyllic setting offers stunning views of the surrounding countryside and the opportunity to meet fellow travelers while feasting on fresh, organic farm food, making it a highlight of your Tuscan journey.
San Gimignano
Discover the medieval charm of San Gimignano, a UNESCO World Heritage Site famed for its towering skyline. Once boasting 72 towers, San Gimignano still showcases 14, earning it the nickname 'Little Manhattan of Tuscany.' Wander through its picturesque streets and squares, exploring landmarks pointed out by your guide. San Gimignano's unique blend of history and architecture offers a glimpse into Tuscany's past, making it a captivating destination for history enthusiasts and casual travelers alike.
Piazza della Cisterna, San Gimignano
Step into the heart of San Gimignano at Piazza della Cisterna, a captivating square that once hosted festivals and tournaments. This picturesque piazza, also a setting for films, leads to the renowned Gelateria Dondoli, known for its award-winning gelato. Indulge in the world's best gelato while soaking in the atmosphere of this historic square. Piazza della Cisterna offers a taste of San Gimignano's rich cultural heritage and a delightful sensory experience.
Piazza del Duomo, San Gimignano
Visit Piazza del Duomo, the religious and political center of San Gimignano, home to the Collegiata (Duomo). Marvel at the 14th-century frescoes adorning the cathedral's interior. For panoramic views, climb the Torre Grossa, one of the medieval towers in the piazza. Piazza del Duomo combines artistic beauty with historical significance, providing a glimpse into San Gimignano's religious and political past.
La Rocca, San Gimignano
Ascend to La Rocca behind the Duomo for stunning views of San Gimignano's skyline. This peaceful setting, with olive trees and remnants of the 14th-century Medici fortress, offers a serene escape. Climb to the top of the garden walls for breathtaking vistas of the towers and surrounding landscape. La Rocca provides a tranquil retreat with unforgettable panoramic views, capturing the essence of San Gimignano's beauty.
Pisa
Journey to Pisa, home of the iconic Leaning Tower, and explore the Square of Miracles. Marvel at the white marble buildings glowing against the lush green lawns. This UNESCO World Heritage site offers a glimpse into Pisa's architectural and historical wonders, making it a must-see destination on your Tuscan tour.
Leaning Tower of Pisa
Experience the wonder of the Leaning Tower of Pisa, an architectural marvel that defies gravity. Ascend to the top for breathtaking views of the Square of Miracles, the city, the Arno River, and the surrounding countryside. The climb itself is an adventure, with the tower's 기울어짐 (leaning) creating a unique and slightly dizzying experience. The Leaning Tower of Pisa is a symbol of Italy and an unforgettable highlight of any visit to Tuscany.
Return to Florence
Conclude your Tuscan adventure with a return to Florence, enriched with memories of medieval towns, culinary delights, and iconic landmarks. Reflect on the beauty of Siena, the rustic charm of Fattoria Poggio Alloro, the tower-studded skyline of San Gimignano, and the gravity-defying Leaning Tower of Pisa. Your camera full of pictures and heart full of memories, cherish the friendships forged and the beauty witnessed on this unforgettable journey.
Know Before You Go
This Tuscany day trip includes wine tasting of four varieties, free time to explore the towns, a hearty farmhouse lunch with veggie and gluten-free options, a professional English-speaking tour guide for the whole day, a guided walking tour of Siena with entrance fee to the cathedral, and an air-conditioned vehicle. What is not included is gratuities, hotel pickup and drop-off, and food and drinks unless specified. The meeting point is at Santa Maria Novella Train Station in Florence. After visiting Siena, San Gimignano, and Pisa, the tour returns to Florence.
Hot Tip
Wear comfortable shoes, as there is a lot of walking involved. Also, bring a water bottle to stay hydrated, especially during the summer months!