Exploring Tuscany’s Classics: Pisa and San Gimignano from Florence – A Detailed Look
Thinking about ticking off some of Tuscany’s most iconic spots without the hassle of public transport or group bus tours? This private Pisa and San Gimignano Tour from Florence might be just what you need. Designed for travelers who prefer a flexible, personalized experience, it promises a full day of exploring with your own driver at the wheel.
What we love about this tour is how it combines convenience with freedom. First, it’s a private transport experience, meaning no crowded buses or rushed schedules. Instead, you get to enjoy your day at your pace, with plenty of time at each stop to take photos, wander, and soak in the views. Second, the scenic drive through Tuscany’s rolling hills is a highlight in itself, offering countless opportunities for photos of the landscape.
One thing to bear in mind is the cost — at just over a thousand dollars for up to 8 people, it’s a pricier option. But considering the private service, hotel pickup, and the flexibility it offers, many travelers find it’s worth the splurge. This tour is particularly suited for those who want a more exclusive experience or are traveling with a group and prefer personalized attention over group tours. If you enjoy independence but still want the convenience of transportation, this trip strikes a good balance.
Key Points

- Private, hassle-free transportation from Florence allows for relaxed exploration.
- You get significant free time in Pisa and San Gimignano to explore at your own pace.
- The scenic drive offers stunning views of Tuscany’s countryside.
- It’s well-suited for groups up to 8, making it a good value for families or friends traveling together.
- The tour is flexible with timing and stops, maximizing your personal interests.
- Optional lunch and wine tasting can be added on the spot but aren’t included in the base price.
What You Can Expect from the Tour

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Hassle-Free Private Transport

One of the biggest perks of this tour is the round-trip private vehicle. Forget about navigating public transit or joining a large bus group. Your driver, who speaks English, handles all the logistics, letting you focus on the sights. The pickup is included, which simplifies your morning — no need to find your way to a meeting point.
The Pisa Stop: The Leaning Tower and Miracles’ Square

You’ll arrive right by the famous Leaning Tower of Pisa, arguably Italy’s most recognizable monument. The tour allocates about 1 hour and 30 minutes here — plenty of time to stroll around the square, snap photos, and appreciate the architecture. Since it’s a free-standing stop, you can take your time getting that perfect shot of the tower tilting at just the right angle. The Miracles’ Square is packed with other historical marvels, but the tower remains the highlight.
Piazza dei Cavalieri: A Hidden Gem

Next, you’ll visit the Piazza dei Cavalieri, a less crowded but equally beautiful square tucked behind Pisa’s main square. Here, you’ll have about 15 minutes — enough to admire the architecture and enjoy the tranquil atmosphere. It’s a good way to see a different side of Pisa beyond the typical tourist stops, even if just for a brief moment.
The Drive Through Tuscany’s Hills

After Pisa, the landscape shifts to those classic rolling hills of Tuscany. The drive itself becomes part of the experience, with photo stops along the way to capture the lush scenery. Expect about 1 hour and 15 minutes of scenic ride, which offers a wonderful backdrop for photos and a taste of Tuscany’s tranquil countryside.
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San Gimignano: Medieval Charm and More

Your final destination is San Gimignano, famed for its medieval towers and well-preserved old town. You’ll have about 1 hour and 30 minutes here, enough time to wander the narrow cobbled streets, browse local shops, and perhaps sample some regional wines. The town’s architecture and towers make for fantastic photos, and its lively atmosphere is perfect for an afternoon wander.
The Experience: A Closer Look

The Value of a Private Tour

The cost of around $1,026 might seem steep at first glance, but it reflects the personalized experience, private vehicle, and hotel pickup. For groups up to 8, this works out to be a reasonable per-person rate, especially considering the convenience. Plus, you avoid the chaos of crowded tours, giving you control over your schedule and pace.
The Flexibility
Unlike large bus tours that stick to strict schedules, this private experience allows you to spend more or less time at each stop if you wish. The driver is there for your comfort, and you can tailor your visit based on your interests. The inclusion of hotel pickup and drop-off is a big plus, especially if you’re staying outside the city center or want to avoid navigating Florence’s streets with luggage.
Food and Wine Options
While lunch and wine tasting aren’t included, you can plan to dine in Pisa or San Gimignano, both known for their fantastic food. The option to add wine tasting on the spot might be tempting if you’re a wine enthusiast, especially considering Tuscany’s reputation for fine wines. Just keep in mind that this will be paid directly during the day.
The Experience Beyond the Sights
Based on reviews, the driver, such as Emanuele, can make a difference. Travelers have praised drivers for their phenomenal service, making the day even more enjoyable. The views of the Tuscan countryside are often highlighted as a favorite part of the trip, and the opportunity to explore independently means you can linger longer or skip parts that don’t interest you.
Who Is This Tour Best For?
If you’re someone who values comfort, flexibility, and personalized service, this private tour is a solid choice. It suits groups or families who want to avoid the crowds and enjoy a more relaxed pace. It also benefits travelers who appreciate stunning scenery and the freedom to explore without feeling rushed.
However, if you’re mainly seeking a very budget-friendly, comprehensive group tour, this might be more than you need. Also, keep in mind that the price doesn’t include meals or wine tastings, so plan accordingly.
Final Thoughts
This Pisa and San Gimignano Tour from Florence offers an elegant way to see two of Tuscany’s most beloved towns without the fuss of navigating on your own. The private transportation, flexible schedule, and scenic drive make it a good fit for travelers seeking comfort and independence. The stops at Pisa’s iconic tower and San Gimignano’s medieval towers provide picture-perfect moments, while the drive through Tuscany’s hills adds a sense of calm and beauty to the day.
If you’re after a more exclusive, tailored experience and don’t mind the price tag, this tour can be a highlight of your Tuscany trip. It’s especially ideal for groups who want their own space and the chance to explore at their own speed, all while enjoying the stunning views that make Tuscany so special.
Pisa and San Gimignano Tour from Florence
“Emanuele was our driver and he was phenomenal!! We had such an amazing experience going to Pisa and San Gimignano from Florence.”
FAQ
Is hotel pickup included?
Yes, the tour includes hotel pickup and drop-off, making the start and end of your day super convenient.
How long is the total tour?
The entire day lasts about 8 to 9 hours, giving plenty of time at each stop and during the drive.
What’s the maximum group size?
Up to 8 people can join, making it a cozy, private experience.
Are meals included?
No, meals and wine tastings are optional and paid separately if you choose to add them during the trip.
Can I customize the stops?
While the itinerary is set, the private nature of the tour offers some flexibility to spend more or less time at each location.
Is this a good tour for families?
It can work well for families or groups who prefer private transport and flexibility, but keep in mind the total duration and walking involved.
What’s the main advantage of this tour?
The main advantage is the combination of personalized service, scenic drives, and free time at each location — a much more relaxed alternative to large group tours.
How much does it cost?
It costs about $1,026.63 per group, which is quite reasonable for a private experience of this scope, especially for a group of up to 8.
This tour strikes a nice balance between comfort, flexibility, and a memorable experience of Tuscany’s highlights. Whether you’re after iconic landmarks, stunning countryside views, or just a relaxed day away from the hustle, it’s worth considering.
More Tours in Florence
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