Pisa and San Gimignano Tour from Florence

Exploring Tuscany’s Charm: Pisa and San Gimignano from Florence

If you’re looking to experience two of Tuscany’s most iconic towns without the hassle of navigating trains or buses, this private tour from Florence is a smart choice. For around $1,027 per group (up to 8 people), you get a full day of sightseeing, culture, and relaxed exploration across approximately 8 to 9 hours. Your personal driver, Emanuele, will pick you up directly from your accommodation, whisking you away in a comfortable private vehicle through the rolling hills of Tuscany. The stops include the famous Leaning Tower of Pisa with its photo-perfect tilt, and the medieval marvel of San Gimignano, renowned for its tall towers and excellent wines.

Two things we particularly love about this experience: first, the freedom to explore each town at your own pace—whether you want to snap the perfect photo of Pisa’s Leaning Tower or wander San Gimignano’s narrow streets and boutique shops. Second, the stunning countryside views along the drive, which give you a real sense of Tuscany’s character beyond the towns. A possible consideration is that this is a fairly full day, so if you’re prone to sensory overload or prefer more structured group activities, you might find the flexible schedule a bit hectic.

This tour suits travelers who enjoy personalized experiences, value comfort and flexibility, and want to see two highlights in one day without rushing. It’s especially great for those who appreciate authentic, independent exploration within a guided framework.

Key Points

• Private transportation ensures comfort and flexibility.
• Free time at each stop allows for personal exploration and photos.
• Scenic drive through Tuscany’s famous rolling hills offers memorable views.
• Visit two UNESCO sites: Pisa’s Leaning Tower and San Gimignano’s medieval skyline.
• Ideal for small groups looking for a personalized, hassle-free day.
• Cost reflects exclusive service with a private driver and hotel pickup.

A Closer Look at the Pisa and San Gimignano Tour from Florence

When we think of Tuscany, images of rolling hills, historic towns, and mouthwatering wines come to mind. This tour makes it possible to see some of those sights comfortably and conveniently. The day begins with pickup from your Florence hotel, a feature that means you won’t need to worry about finding meeting points or public transportation. Instead, you’ll step into a private vehicle driven by a courteous, knowledgeable guide—Emanuele, as one review enthusiastically noted—who elevates the experience with friendly service and local insights.

The Pisa Stop: A Photo-Opportunity and Iconic Landmark

Your first destination is the Leaning Tower of Pisa, the region’s most recognizable monument. The tour allocates about an hour and a half here, which is enough to stroll around Miracles’ Square—a UNESCO World Heritage Site—and capture some memorable pictures. The beauty of this stop lies in its simplicity: you’re right next to the tower, so you can take your time to admire the architecture, maybe get a few shots from different angles, or just soak in the atmosphere of this world-famous site.

One reviewer, Amber, shared, “Emanuele was our driver and he was phenomenal!! We had such an amazing experience going to Pisa and San Gimignano from Florence.” This highlights how a dedicated driver can turn what could be a rushed sightseeing moment into a relaxed, personal experience. Plus, with no admission fees at this stop, you get to enjoy the sight without extra costs.

Hidden Gems: Piazza dei Cavalieri and Tuscan Countryside Views

Next, the tour includes a quick visit to Piazza dei Cavalieri, a square often overshadowed by the Leaning Tower but equally worth seeing for its architectural elegance and historical significance. You’ll have around 15 minutes here to appreciate its beauty and maybe snap a few more photos.

Then, the journey continues across the Tuscan hills, offering postcard-worthy views of vineyards, olive groves, and charming villages. The drive itself, about 1 hour and 15 minutes, passes quickly, thanks to the breathtaking scenery and opportunities for quick photo stops along the way. These vistas are what make Tuscany so enchanting, and having a private driver means you can pause at spots that catch your eye, rather than being confined to a rigid schedule.

San Gimignano: The Medieval Skyline

The highlight of the afternoon is San Gimignano, often called the “Medieval Manhattan” for its skyline of well-preserved towers. You’ll have approximately 90 minutes to wander the cobbled streets, browse local shops, and enjoy the town’s famous wine—an optional tastings are available, though not included in the price. The town is a UNESCO World Heritage site, and its towers provide a dramatic backdrop for exploring narrow alleys, medieval architecture, and picturesque piazzas.

One traveler noted, “San Gimignano is known for its incredible architecture, shops, and excellent wines,” capturing what makes this town so special. You might find yourself sampling local Vernaccia wine or picking up handmade crafts—there’s plenty to discover at a relaxed pace.

The Value of Flexibility and Personal Service

With all included taxes, fees, and a private English-speaking driver, this tour offers value in convenience and comfort. The flexibility to explore each town without rushing is a significant advantage, especially compared to typical group bus tours, which can feel impersonal and hurried.

The tour is designed for small groups—up to 8 people—meaning we experienced a more intimate, tailored day. The private vehicle and hotel pickup are especially handy for avoiding the logistical headaches of public transit, which can be tricky in unfamiliar towns.

Optional Extras and Costs

Lunch and wine tasting are not included, so you can choose to dine at local trattorias or sample wines at your leisure. This allows you to tailor the experience to your tastes and budget, rather than being locked into preset schedules or menus.

How This Tour Compares to Others

While there are larger group excursions that include Pisa and San Gimignano, this private option offers a more relaxed pace, personalized service, and the freedom to explore each town as you wish. With a high rating of 5 stars based on 7 reviews, travelers consistently praise the quality of the driver and the overall experience.

If you’re considering similar experiences, you might also look into tours that include lunch or additional stops, but this tour hits a sweet spot for those who want quality over quantity, with the comfort of private, door-to-door service.

Who Should Book This Tour?

This experience is perfect for couples, small families, or friends seeking a relaxed, personalized day in Tuscany. It’s especially well-suited for those who value flexibility—whether to linger longer in a favorite spot or take extra photos. It’s also ideal if you prefer avoiding the crowds and structured schedules common in larger bus tours. If you’re a lover of scenic drives, medieval architecture, and tasting local wines, this trip hits many of your must-do’s in one day.

The Sum Up: Is This Tour Worth It?

For travelers wanting to see Pisa’s Leaning Tower and San Gimignano’s medieval skyline in a single, relaxed day, this private tour offers excellent value. The comfort of private transport, the personal touch of a dedicated driver, and the freedom to explore at your own pace make it a standout choice. It’s especially suited for those who appreciate scenic drives, authentic experiences, and the flexibility to customize their day.

While it’s a bit on the pricier side, the convenience, comfort, and quality of the experience make it worth considering—particularly if your goal is a stress-free, memorable day in Tuscany. This tour provides a balanced combination of guided ease and independent discovery, perfect for travelers who want the best of both worlds.

FAQs

What is included in the price of this tour?
All taxes, fees, and handling charges are included, along with a private vehicle, a personal English-speaking driver, and hotel pickup and drop-off.

Is this tour suitable for small groups?
Yes, the tour is private and designed for groups up to 8 people, offering an intimate experience with personalized service.

How long do we spend at each location?
You have approximately 1 hour 30 minutes at Pisa, 15 minutes at Piazza dei Cavalieri, and around 1 hour 30 minutes in San Gimignano. The drive through Tuscany’s countryside takes about 1 hour 15 minutes with photo stops.

Are meals or wine tastings included?
No, lunch and wine tastings are optional extras and are paid for on the spot if you choose to indulge.

Can I customize the itinerary?
While the core stops are fixed, the private nature of the tour means you have some flexibility to spend more or less time at each location or request additional stops.

What if I want to cancel?
You can cancel up to 24 hours in advance for a full refund. Cancellations made less than 24 hours before the tour start are not refundable.

Is this tour accessible for travelers with mobility issues?
The tour involves walking around towns that may have cobblestone streets, so it may not be suitable for all mobility levels.

How is the driver?
Based on reviews, drivers like Emanuele are praised for their professionalism and friendliness, making the experience more enjoyable.

What should I bring?
Comfortable shoes for walking, a camera, and perhaps some snacks or water for the drive are recommended.

Is there a possibility of exploring other towns?
This tour is focused on Pisa and San Gimignano, but private tours can sometimes be tailored to include additional stops if arranged in advance.

This private Pisa and San Gimignano tour from Florence offers a seamless, flexible, and memorable way to experience Tuscany’s highlights. Perfect for those who want comfort, authenticity, and the freedom to explore at their own pace.