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Discover Tuscany’s highlights on a 9-hour private shore excursion from Livorno, visiting Siena, San Gimignano, and Monteriggioni with a friendly, knowledgeable driver.

This 9-hour private tour offers a taste of Tuscany’s iconic towns, led by an English-speaking driver who guides you through some of Italy’s most picturesque spots. For $1,144.88 per group (up to 8 people), you get the convenience of door-to-door pickup directly from Livorno port, combined with a comfortable Mercedes van equipped with free Wi-Fi. The tour provides ample time to explore each location at a relaxed pace, making it ideal for those who want to see Siena, San Gimignano, and Monteriggioni without the hassle of organizing transport or guides.
While the itinerary is rich with highlights, it’s worth noting that entry to Duomo di Siena and some other monuments is not included. This tour is well-suited for travelers who enjoy scenic drives, historic towns, and a taste of Tuscany’s famous wines and architecture. Advance booking is recommended, with most groups reserving their spot around 79 days in advance.

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The tour begins promptly at 7:45 am with a pickup right at the Livorno port — specifically at Piazzale dei Marmi, 12. This convenient start point ensures a smooth beginning, with no need to worry about transportation logistics. The private vehicle then departs for the scenic drive through the Tuscan countryside, where rolling hills, olive trees, and vineyards fill the view.
The air-conditioned Mercedes van offers a comfortable ride, with Wi-Fi available for staying connected or sharing photos along the way. The driver acts as your guide, offering commentary about the regions you pass, though they are not licensed guides for museums or monuments.

The first stop is Monteriggioni, a medieval castle that ranks among the most well-preserved in Italy. The 45-minute visit offers free time for a coffee break amid the castle’s ancient walls, which provide a perfect backdrop for photos. This site’s impregnability and history make it a favorite for history buffs and those who appreciate medieval architecture.
Since admission tickets are free, you can spend your time exploring the fortress, strolling along the ramparts, or just soaking up the atmosphere of this historic site. The driver remains available for questions or quick tips on what to see.
Next, the tour moves to Siena, where the Basilica di San Domenico stands out as a key highlight. In just 20 minutes, visitors can admire this church and see the Relic of Santa Caterina, which is a significant religious artifact. This stop offers a concentrated dose of Siena’s spiritual and artistic heritage.
The basilica’s exterior and interior reflect Siena’s distinctive Gothic style, and the relic adds a layer of historical intrigue. This stop is ideal for those interested in religious art, saints, and Siena’s local traditions.
The tour then stops in front of the Duomo di Siena (Santa Maria Assunta) for 45 minutes. While entry tickets are not included, the exterior alone is stunning, with its intricate façade and striped marble design. The proximity allows for excellent photo opportunities and a chance to admire Siena’s iconic cathedral from outside.
This stop offers a relaxed window for photos and a chance to appreciate Siena’s architectural grandeur without the additional cost of museum entry.

The largest stop is Piazza del Campo, where 1 hour and 30 minutes are allocated. This impressive shell-shaped square is the social and historical hub of Siena. The Torre del Mangia, Palazzo Pubblico, and Fonte Gaia make this square truly photogenic and lively.
This free, open-air exploration allows plenty of time to stroll, soak in the lively atmosphere, and admire the monuments. It’s the perfect spot to understand why Siena’s Palio horse race and its architecture captivate visitors.

The journey continues to San Gimignano, renowned for its medieval towers and reputation as Tuscany’s “Manhattan”. The 2-hour stay is designed for enjoying the town’s spectacular skyline, tasting La Vernaccia, one of Tuscany’s most famous white wines, and sampling the world’s best gelato.
San Gimignano’s towers once served as symbols of wealth and power, and today they create a remarkable skyline. Visitors can explore the narrow streets, visit local shops, or simply enjoy the panoramic views. The free time allows for a relaxed visit with plenty of opportunities for photos and local tastings.

The tour concludes with a 2-hour drive back to Livorno port, giving everyone time to relax and reflect on the day’s sights. The private vehicle ensures a smooth, comfortable ride, and the driver may share further insights about the regions passed.
This ending segment wraps up a full day of exploration, leaving ample time before the ship departs or continues onward.
The tour price of $1,144.88 covers the entire 9-hour experience, including private transportation, air conditioning, and all fees and taxes. The free Wi-Fi on most vehicles adds to the convenience, especially for sharing your adventures or staying connected.
Food and drinks are not included, so travelers should plan to bring snacks or purchase options during stops. The tour is designed for most travelers, with drivers providing commentary from inside the vehicle. It is not a guided tour inside the sites themselves, as drivers are not licensed guides for museums or churches.
This private shore excursion best suits those wanting a flexible, comfortable day exploring Tuscany’s most famous towns without the worry of navigation or group tours. It’s especially attractive for small groups or families who prefer a personalized experience with plenty of free time at each stop.
The stunning views, historic architecture, and wine tastings make it a great choice for culture lovers, wine enthusiasts, and photographers, though those seeking detailed guided museum visits might find some limitations.
This tour offers a comprehensive taste of Tuscany’s most beloved towns in a relaxed, private setting. The comfort of a Mercedes van with Wi-Fi, combined with ample free time in each location, makes it a practical choice for travelers wishing to maximize their port day.
While not including entry tickets to certain sites might be a downside for some, the overall value and convenience of this private excursion shine through. It fits best for those who want a personalized, scenic, and hassle-free way to experience Siena, San Gimignano, and Monteriggioni in one memorable day.
“We enjoyed the drive through the beautiful Tuscan countryside. The areas visited were nice but very crowded with tourists. Our driver was personabl…”
Is this tour suitable for all ages?
Yes, the tour is designed for most travelers and involves no strenuous activity.
Are lunch options included?
No, lunch is not included, so plan to bring snacks or purchase food during stops.
Does the driver give guided commentary inside the sites?
No, the driver provides commentary from inside the vehicle but is not licensed to guide inside museums or churches.
What is the pickup location?
Pickup is at Piazzale dei Marmi, 12 at Livorno port, starting at 7:45 am.
Can I cancel the tour for a full refund?
Yes, cancellation is free if made at least 24 hours in advance.
Is Wi-Fi available during the trip?
Yes, most vehicles are equipped with free Wi-Fi.
What are the main highlights of the stops?
Highlights include Monteriggioni’s medieval walls, Siena’s Piazza del Campo, and San Gimignano’s towers and wine.
Are tickets to attractions included?
No, tickets to sites like Duomo di Siena are not included and must be purchased separately if desired.
How long is the total travel time?
The entire tour lasts approximately 9 hours, including all stops and the return journey.
Is this a guided tour inside the towns?
No, it is a private transportation experience with commentary from the driver, not a guided tour inside the sites.