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Explore two authentic Tuscan hill towns—San Gimignano and Volterra—on a private, 9-hour tour from Livorno with expert guides, comfortable transport, and flexible timing.
If you’re cruising into Livorno and craving a genuine taste of Tuscany beyond the typical tourist spots, this private tour to San Gimignano and Volterra is a smart choice. It offers an intimate, personalized experience with the flexibility to explore at your own pace, all while avoiding the crowded groups often found on less tailored excursions. The focus here is on discovering lesser-visited medieval towns with rich stories, breathtaking views, and authentic local charm.
What really stands out about this tour is the customized approach—you’re traveling in a comfortable Mercedes-Benz Vclass minivan, with a driver-guide who’s knowledgeable and enthusiastic. The itinerary is well-structured to balance sightseeing, leisure, and shopping, making it a great fit for travelers who value quality over quantity. However, keep in mind that this is a full-day experience that involves some walking and moderate physical activity, especially in the cobbled streets of these historic towns.
This tour is best suited for those who’ve already ticked off Pisa and Florence from their list and want to venture a little deeper into Tuscany’s heart. It’s perfect for travelers looking for authentic experiences, intimate scenery, and insights from local guides, rather than large-group sightseeing.


For a more personal experience, these private Livorno tours deliver individual attention
Your day kicks off at 8:30 am, with a seamless pickup right in front of your cruise ship in Livorno. From there, a comfortable Mercedes-Benz Vclass minivan whisks you away through the scenic Tuscan landscape. This is not just about transportation — your driver guide is there to enhance your day with insights and local tips, making the journey itself part of the adventure.
Your first stop is San Gimignano, a town renowned for its medieval towers and elegant stone architecture. After approximately 1 hour and 30 minutes drive through rolling hills and lush valleys, you’ll arrive at this UNESCO-listed site, famously called “The Town of the Fine Towers”.
Once inside the fortified walls, you’ll have about two hours to explore at your own pace. The Piazza Cisterna is a focal point — a triangular-shaped square surrounded by cafés and shops, perfect for soaking in the atmosphere or browsing local souvenirs. An important highlight is the Collegiata, the Romanesque cathedral adorned with frescoes, which offers a glimpse into the town’s spiritual and artistic heritage.
The beauty of San Gimignano lies in its mix of history, architecture, and vibrant street life. Whether you’re wandering through narrow alleys, shopping for local ceramics or saffron, or simply taking photos of the iconic towers, you can do so without the rush of larger tours.
Next, about 40 minutes drive, is Volterra, a hilltop town with roots stretching back to Etruscan times. The town’s golden-stone walls and red-tiled roofs create a picture-perfect Tuscan scene. Here, you’ll get roughly two hours to explore on your own, with the driver-guide providing tips and suggestions.
Your first stop is the Piazza dei Priori, often regarded as Italy’s most beautiful square. It’s a lively, striking space surrounded by towers and medieval palaces, perfect for soaking in the history and architecture. From there, a short walk takes you to Piazza San Giovanni, where you can admire ancient temples, the Baptistery, and the Cathedral—each offering insights into the town’s deep past.
Shopping here is a treat, especially if you’re keen on alabaster crafts, a local specialty. The town’s atmosphere is quieter than San Gimignano’s, with fewer travelers, making it easier to enjoy the authentic Tuscan vibe.
This is a private tour, so your driver-guide is flexible to accommodate your interests, whether that means more time in a specific area or recommendations for local eateries (though lunch isn’t included). The tour also offers optional add-ons like a visit to a top-rated winery, perfect for wine enthusiasts eager to pair their sightseeing with tastings.

At $555.27 per person, this tour may seem steep at first glance, but the value lies in the personalized experience, luxury transport, and expert guidance. Booking well in advance (often 256 days ahead on average) indicates high demand, and the inclusion of pickup and drop-off at Livorno pier makes it a hassle-free option for cruise travelers.
Since admission fees to museums aren’t included, you’ll want to budget extra if you plan to visit churches or galleries. Still, the overall experience provides a balanced mix of sightseeing, shopping, and leisure, which many travelers find worth the price.
One reviewer, Traci_K, describes the experience as “a must,” highlighting the prompt pick-up and the driver Sonny’s welcoming attitude. She appreciated the comfortable van and the flexibility to explore San Gimignano’s streets at her own pace, emphasizing the value of having a local guide who’s also a friendly driver.
This experience is ideal for travelers who value a tailored, intimate experience over large-group excursions. It’s perfect if you’ve already explored the main cities and are looking for authentic, less touristy towns with stunning scenery and history. Those with moderate physical fitness will enjoy wandering cobbled streets and piazzas, but it’s not suited for anyone with mobility issues.
Wine lovers might find the optional winery visit a bonus, adding a gastronomic dimension to the day. This tour suits curious travelers who want to see the real Tuscany, away from the crowds but with plenty of sights, stories, and authentic charm.
This private tour offers an engaging way to experience two of Tuscany’s most captivating medieval towns. With personalized service, comfortable transportation, and flexible timing, it caters well to travelers seeking an authentic, relaxed day away from the busy cruise port. The emphasis on local insights and scenic exploration makes it stand out from more generic excursions.
While it’s priced higher than some group tours, the value is reflected in the quality of the experience—without the rush or crowding. For those who want to enjoy Tuscan history and scenery at their own pace, this tour is a satisfying and memorable choice.

Is transportation included in this tour?
Yes, transportation is provided in a comfortable Mercedes-Benz Vclass minivan, with pickup and drop-off right in front of your Livorno cruise ship.
Can I customize the sightseeing time?
Since it’s a private tour, your driver-guide can adapt the timing to suit your interests, whether that means more time in one town or for shopping.
Are entrance fees included?
No, the tour price covers transport and guide services, but admission fees to museums or sites are not included, so plan extra if you want to visit churches or galleries.
How long is the drive between towns?
The drive from Livorno to San Gimignano takes about 1 hour and 30 minutes, and from San Gimignano to Volterra about 40 minutes.
What should I wear and bring?
Comfortable shoes are recommended given cobbled streets, and bringing water, sunscreen, and a camera is advised for sightseeing and capturing views.
Is this tour suitable for all physical fitness levels?
Moderate physical activity is involved, mainly walking and exploring cobbled streets, so travelers should have a moderate fitness level for comfort.
This private tour from Livorno to San Gimignano and Volterra offers an authentic and relaxed way to discover some of Tuscany’s most enchanting spots. Perfect for those who love history, scenic views, and local culture, it promises a memorable day crafted just for you.