Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

This Tuscany Day Trip from Florence offers an engaging way to see some of the region’s most iconic towns in just over 12 hours, all for $121.91 per person. The tour covers Siena, San Gimignano, Pisa, and includes a lunch at a winery with wine tasting. Guided by knowledgeable guides and comfortably transported in an air-conditioned coach, this tour is ideal for visitors with limited time who want to experience Tuscany’s art, history, and countryside.

What truly sets this trip apart is the opportunity to see multiple towns in one day while enjoying local food and wine in a scenic setting. The tour earns a 5.0 rating from over 18,500 reviews, with 97% recommending it, pointing to consistent quality and guest satisfaction. As a practical note, the tour is long (about 12 hours), so it suits those prepared for a full day. Limited accessibility options mean it’s best for those with moderate physical fitness.

Key Points

• Full-day itinerary covering Siena, San Gimignano, Pisa, and a Tuscany winery
• Guided tour with expert commentary, including entry to Siena Cathedral
• Wine tasting and hearty Tuscan lunch at a family-run vineyard (available as an upgrade)
• Flexible free time in Siena, San Gimignano, and Pisa to explore independently
• Climb the Leaning Tower of Pisa available if you choose the upgrade
• Tour departs from Florence’s Santa Maria Novella train station at 7:45 am and returns around 8:30 pm

Starting Your Day at Florence’s Santa Maria Novella Station

The tour begins early, with meet-up at 7:45 am at the front of Santa Maria Novella train station. The guide holds a Walkabout Tours sign by the taxi stand. After a brief walk, guests board a comfortable, air-conditioned coach for the approximately 75-minute drive to Siena. The lively commentary from the guide during the transfer sets the tone for a day filled with insights into Tuscany’s history, towns, and culture.

The punctual start and organized logistics are praised, helping ensure a smooth beginning to a long but rewarding day. The small group size, capped at 40 travelers, keeps the atmosphere friendly and manageable.

Exploring Siena’s Medieval Charm and Art

The first major stop is Siena, a UNESCO World Heritage Site famous for its medieval architecture. Upon arrival, a guided walking tour with a local guide takes about an hour. The tour includes highlights like Piazza del Campo, the Siena Cathedral, and the historic contrade districts.

Guests visit Piazza del Campo, known for its sea-shell shape and vibrant Palio horse race. The Siena Cathedral, with its remarkable marble floor—decorated with over 50 artworks—is a standout. Visitors have time afterward to shop or relax at open-air cafes, enjoying the lively city atmosphere.

Additional stops include Piazza Salimbeni, home to Siena’s historic bank, Monte dei Paschi di Siena, founded in 1472, and the Contrada della Torre, where the unique districts called contrade each have their own symbols and rivalries. These details give a vivid picture of Siena’s wealth, tradition, and local pride.

Wine Tasting and Tuscan Lunch at Fattoria Poggio Alloro

After exploring Siena’s streets, the group travels about 45 minutes to Fattoria Poggio Alloro, a family-run organic vineyard. Here, guests enjoy a Tuscan lunch featuring homemade pasta, cured meats, cheeses, and biscotti, paired with four varieties of wine during a tasting session.

The lunch is described as hearty and authentic, with fresh ingredients and a spectacular view of the rolling countryside. The winery staff take care to package products for safe transport home and offer shipping options for larger purchases. The experience is praised for its relaxed atmosphere and quality food.

Guests have about an hour and a half at the vineyard to enjoy the meal, admire the vista, and browse the local products for sale.

Discovering the Medieval Towers of San Gimignano

Following lunch, a 15-minute drive takes visitors to San Gimignano, a UNESCO World Heritage Site characterized by its medieval towers—originally 72, now 14 remain. Often called the “Manhattan of Tuscany,” this town is famed for its skyline of towers and cobbled streets.

Here, guests receive a map from the guide and are free to explore at their own pace. Key landmarks include Piazza della Cisterna, a historic square with beautiful architecture and award-winning gelato at Gelateria della Piazza, renowned for its local flavors. The Piazza del Duomo contains a small but stunning cathedral decorated with 14th-century frescoes.

Guests can also climb the Torre Grossa—a medieval tower offering spectacular views over San Gimignano. Behind the Duomo, Rocca of Montestaffoli provides a peaceful spot with breathtaking vistas of the town’s skyline, ideal for photography and relaxing.

En Route to Pisa for the Final Stop

After exploring San Gimignano, the coach makes an about 1.5-hour scenic drive to Pisa. The journey passes through classic Tuscan landscapes, with the guide sharing insights about Pisa’s history and architecture.

Once in Pisa, the group heads straight to Piazza dei Miracoli, a world-famous square with the Leaning Tower, Pisa Cathedral, Baptistery, and Camposanto. The white marble buildings glow against the green lawns, creating a postcard-perfect setting.

Guests have roughly an hour to explore these monuments. If booked as an upgrade, skip-the-line tickets allow climbing the Leaning Tower for breathtaking views and a bit of dizzying fun. The baptistery also offers spectacular interior frescoes and viewing platforms.

Climbing Pisa’s Leaning Tower or Visiting the Cathedral

The Leaning Tower of Pisa is a highlight for many. The climb involves about 150 steps and offers impaning panoramic views of Pisa, the Arno River, and surrounding countryside. The view from above shows the slope of the tower and provides a unique perspective of the historic square.

If climbing the tower isn’t preferred, visiting the interior of the cathedral or baptistery provides a rich artistic experience. The tickets can be bought on-site, and timed entry is recommended to avoid disappointment.

Returning to Florence in the Evening

After completing the sightseeing in Pisa, the group boards the coach for about an hour back to Florence. The return journey features more commentary from the guide, often sharing additional stories and insights. The tour concludes around 8:30 pm, with guests returning to Santa Maria Novella station.

This full-day schedule is praised for its efficient pacing, allowing enough time to enjoy each stop without feeling rushed. The organized transfers and guided commentary make it easier for guests to relax and absorb the experience.

The Guide and Overall Experience

The guides are consistently praised for their knowledge, friendliness, and clarity, with Noemi receiving particular acclaim for her fluency in multiple languages and engaging storytelling. Guests appreciate guides who check in on everyone, make the experience fun, and share personal insights.

The lunch at the winery and wine tasting are often highlighted as standout moments, offering delicious food and local wines in a scenic setting. The comfortable bus rides and well-organized schedule contribute to a stress-free day, even with the long hours.

Practical Tips and Considerations

While the tour is well-organized, expect to walk about 10 minutes to and from the bus at each stop. The pace is manageable, but those with mobility issues should plan accordingly. Comfortable shoes are recommended, as well as water for hydration during the day.

The long duration makes this tour most suitable for adults or teenagers over 8 years old who are prepared for a full day of sightseeing. Children under 8 cannot climb the Leaning Tower, and all minors need supervision. The optional tower climb is a highlight for those who book the upgrade.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

This comprehensive tour offers a balanced mix of sightseeing, culture, and culinary delights. The expert guides make navigating the towns straightforward, and the scenic drives showcase Tuscany’s picturesque landscapes. The lunch at the winery is a memorable highlight, combining local food, wine, and panoramic views.

While the full schedule is demanding, the organized logistics and informative guides help maintain a relaxed atmosphere. The option to climb the Leaning Tower adds a special touch, making it a popular choice for visitors eager to see many highlights in one day.

This tour is best suited for those seeking an efficient yet immersive experience of Tuscany’s towns, history, and cuisine, with the flexibility to explore independently during free time. The positive reviews and high recommendation rate confirm it’s a dependable choice for a memorable day.

Frequently Asked Questions

What is the starting point for this tour?
It departs from Piazza della Stazione, 14/39, Florence at 7:45 am, meeting at the front of Santa Maria Novella train station.

How long is the tour?
The total duration is approximately 11 to 12 hours, ending around 8:30 pm back in Florence.

Is lunch included?
Lunch is included if you upgrade to the full tour with wine tasting, featuring Tuscan farm food and four wines. Otherwise, it’s an own expense.

Can I climb the Leaning Tower of Pisa?
Yes, if you choose the upgrade that includes tower tickets, you can climb the tower for incredible views.

How much time do I have at each town?
Guests generally have about 1.5 hours in Siena and San Gimignano, and around 1 hour in Pisa, with some flexibility.

Is the tour suitable for children?
Children under 8 are not admitted to climb the tower, and minors must be supervised. The tour involves moderate walking.

What is the guide like?
Guides like Noemi, Mirela, and Gloria are praised for their knowledge, friendliness, and engaging style. Many reviews highlight their fluency in multiple languages and passion for sharing Tuscany’s stories.

Are dietary restrictions accommodated?
Vegetarian options are available for lunch, but gluten-free or other special diets cannot be guaranteed.

Is transportation comfortable?
Yes, guests travel in air-conditioned coaches with well-maintained seats, making the long day more pleasant.

What should I bring?
Bring comfortable shoes, water, and a camera. Dress appropriately for weather conditions.

Can I cancel the tour?
Yes, free cancellation is available up to 24 hours in advance for a full refund.

This Tuscany day trip from Florence offers an organized, informative, and scenic way to experience Siena, San Gimignano, Pisa, and a Tuscan winery in a single memorable day.