Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Exploring Pisa’s Piazza dei Miracoli and the Leaning Tower

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting

Discover Tuscany's highlights with this full-day tour from Florence including Pisa, San Gimignano, Siena, and wine tasting, all for just $52.25 per person.

Exploring Tuscany in a single day becomes a practical delight with the Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting tour offered by Sightseeing Experience. Priced at $52.25 per person, this 11.5-hour journey takes you through four of Tuscany’s most iconic spots, all with comfortable transport and carefully curated stops. The tour departs from Florence’s Train Station at 7:30 am, making it ideal for those eager to maximize their day without the hassle of planning.

This tour is especially well-suited for visitors who appreciate guided insights, scenic drives, and a taste of Tuscany’s renowned wine and cuisine. While it tends to be popular and well-reviewed, a few limitations include the group’s size—up to 60 travelers—and the pacing, which some find a bit hurried, especially at each site. Still, the value for money and the opportunity to see Pisa’s Leaning Tower, wander medieval streets, and sip wine in Chianti make this experience worth considering.

Key Points

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Key Points

  • Affordable full-day tour from Florence at $52.25 per person, with optional upgrades.
  • Includes transportation between Pisa, San Gimignano, Siena, and the Chianti Hills.
  • Well-rated with 4.5 out of 5 stars from over 500 reviews, praised for knowledgeable guides and beautiful scenery.
  • Highlights include Pisa’s Piazza dei Miracoli, lunch and wine tasting at a Chianti vineyard, and free time in medieval San Gimignano and Siena.
  • Comfortable transport equipped with Wi-Fi and air conditioning, though the large group size may limit intimacy.
  • Timing can be tight, with about an hour in each town, which some reviewers find rushed but still rewarding.

Starting Point: Meeting at Florence’s Sightseeing Experience Visitor Center

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Starting Point: Meeting at Florence’s Sightseeing Experience Visitor Center

The tour begins early at the Sightseeing Experience Visitor Center inside the Santa Maria Novella train station in Florence. With a start time of 7:30 am, the trip kicks off with a comfortable GT bus that features Wi-Fi and air conditioning, making the long day more pleasant.

Travelers are advised to arrive promptly as there are no refunds for delays, and punctuality is essential for the smooth running of the schedule. The group size maxes out at 60 people, which helps manage logistics but might feel crowded during busy periods.

Exploring Pisa’s Piazza dei Miracoli and the Leaning Tower

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Exploring Pisa’s Piazza dei Miracoli and the Leaning Tower

The tour’s first major stop is Pisa, where two hours are allocated for a free walking tour. The focus is on the cathedral, baptistery, monumental cemetery, and the famous Leaning Tower. Visitors can admire the architecture and snap photos of the iconic tilt.

An optional climb of the Leaning Tower is available but involves an additional fee and is not suitable for children under 8 years old. The admission tickets for the tower are not included in the base price. The Piazza dei Miracoli also features the largest baptistery in Italy, which is a notable highlight for architecture fans.

The legend of the Monumental Cemetery, which supposedly causes bodies to rot in 24 hours, adds a bit of local folklore to the visit. Some guests find the short stay in Pisa a bit rushed, but the impressive sights make it worthwhile.

Scenic Drive Through the Chianti Hills to a Rustic Winery

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Scenic Drive Through the Chianti Hills to a Rustic Winery

After Pisa, the tour drives along the Strada Statale 222 Chiantigiana, offering stunning views of Tuscany’s rolling hills and vineyards. This scenic drive prepares you for the highlight of wine tasting in Chianti.

At a local winery, the group is welcomed to sample three wines paired with local specialties such as bruschettas, pecorino cheese, and various cold cuts. The tasting lasts approximately 1 hour and 20 minutes, giving ample opportunity to enjoy the authentic flavors of Tuscany’s wine region and learn about local wine production.

While the wine tasting is included in the standard package, some reviews note that the food served may be quite simple, though still enjoyable. The atmosphere in the vineyard provides a relaxing break from the busier sightseeing.

Wandering Medieval San Gimignano’s Cobblestone Streets

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Wandering Medieval San Gimignano’s Cobblestone Streets

Post-lunch, the tour visits San Gimignano, often called the Medieval Manhattan for its skyscraper-like towers. About an hour is dedicated to exploring its cobbled streets, small squares, and craft shops.

In Piazza del Duomo, visitors see the 11th-century Collegiate Church and the early 13th-century architecture that reflects San Gimignano’s golden age. The Piazza della Cisterna offers a triangular shape with noble houses and towers lining the brick pavement, perfect for photos and wandering at your own pace.

This stop provides a medieval charm and photo opportunities, though some may find the time limit to be a bit short for fully soaking in the ambiance.

Siena’s Iconic Piazza del Campo and the Cathedral

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Siena’s Iconic Piazza del Campo and the Cathedral

The journey continues with a panoramic drive through the Chianti countryside to reach Siena. Here, a guided tour (if the guided option is selected) covers the main squares and historic sites.

The main square, Piazza del Campo, is renowned for its shell shape and hosts the famous Palio di Siena horse race twice a year. The cathedral of Siena, built in Romanesque-Gothic style, is a must-see, with its ornate façade and interior featuring stunning artworks.

Guests have around 1 hour and 30 minutes for free time after the guided tour, where they can enjoy local treats like Pan Forte, shop in boutiques, or relax with a coffee. The guided tour in Siena is valued for insightful commentary and local tips.

Optional Guide and Tower Climb Enhancements

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Optional Guide and Tower Climb Enhancements

Travelers can upgrade their experience to include a guide or a tower climb at Pisa. The guide enhances the visit with more detailed explanations and local stories, while the tower climb offers the chance to stand atop the famous leaning monument for panoramic views.

However, the tower climb is not available for children under 8 years old, and the tickets are an additional cost. The guided option is particularly valued for those who want a deeper understanding of the sites.

Pacing and Group Size Considerations

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Pacing and Group Size Considerations

The large group size of up to 60 travelers could make movement and timing feel more rushed, according to some reviews. The bus departs frequently, and long walks from the bus to each site are common, with some stops requiring uphill climbs.

The day’s schedule packs in many visits, which sometimes leads to about an hour per stop. While this covers the highlights, some guests find it limits the depth of their exploration, especially in towns like Siena and San Gimignano.

Practical Tips and Additional Information

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting - Practical Tips and Additional Information

The meeting point at the Florence station emphasizes prompt arrival, as no refunds are offered for delays. The bus is equipped with Wi-Fi and air conditioning, making the long day more comfortable.

For vegetarians or those with dietary restrictions, a special menu can be arranged, but it’s recommended to notify the provider in advance. Children under 8 cannot participate in the Pisa tower climb, and all participants should be prepared for a full day of walking.

The tour is designed to cater to most mobility levels, but the pace may be quick, especially during busy periods. Punctuality is crucial to avoid missing parts of the schedule, and no waiting is expected for late arrivals.

Siena, Pisa, and San Gimignano in a Day: Is It Worth It?

This full-day tour offers a comprehensive look at some of Tuscany’s most famous towns, combined with wine tasting in the Chianti hills. The price point, at just over $52, makes it a cost-effective way to see Pisa’s Piazza dei Miracoli, wander San Gimignano’s medieval streets, and explore Siena’s historic squares.

While the large group size and tight schedule might not suit everyone, the expert guides, scenic drives, and authentic tasting experiences are highly praised. The option to upgrade with a guide or tower climb allows for a more personalized experience.

If you value convenience, scenic drives, and a well-organized itinerary, this tour offers solid value. However, those seeking more relaxed or in-depth exploration might prefer a smaller, more flexible option.

Ready to Book?

Tuscany Experience: Pisa, Siena, San Gimignano & Wine Tasting



4.5

(501)

“This was a great tour. Long but not tiring. The places were great, as well as the lunch served. Only suggestion would be to begin earlier or get ba…”

— Roger F, May 2025

Frequently Asked Questions

What is included in the tour price?
The standard price of $52.25 includes transportation by air-conditioned bus, Wi-Fi, a wine tasting in Chianti, and guided visits in Siena (if selected). Admission tickets for Pisa’s Leaning Tower and guided tour in Siena are optional upgrades.

Can children participate in the Pisa tower climb?
No, the tower climb is not available for children under 8 years old. The base tour is suitable for most ages, but younger children may find the pace challenging.

How long are the stops at each location?
Each stop lasts approximately an hour, with two hours allocated for Pisa. Some find the schedule a bit rushed for towns like Siena and San Gimignano.

Is lunch included?
Yes, lunch at a Chianti winery is included, with local specialties and wine tasting. Specific menus can be vegetarian upon request.

What is the group size?
The tour accommodates up to 60 travelers, which helps manage logistics but may feel crowded during busy times.

Can I upgrade the experience?
Yes, travelers can add a guide or tower climb tickets at an extra cost. The guide adds more detailed commentary throughout the day.

What is the cancellation policy?
You can cancel free of charge up to 24 hours before the tour for a full refund. Cancellations made within 24 hours are not refunded.

Where does the tour start and end?
The tour begins and ends at the Sightseeing Experience Visitor Center inside Florence’s Santa Maria Novella station.

Is this tour suitable for those with limited mobility?
The walking involved and long bus rides may pose challenges. The pace can be quick, especially during busy periods, so mobility considerations should be taken into account.

How is the overall value of the tour?
Considering the price, organized itinerary, scenic drives, and wine tasting, many reviews highlight excellent value, especially for those wanting a comprehensive day trip from Florence.