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Discover Tuscany’s medieval towns of Siena and San Gimignano, plus a Chianti winery, on this private 9-hour shore excursion from Livorno, including port pickup.

For cruise travelers docking in Livorno, this All Tuscany Private Siena San Gimignano & Chianti Livorno Shore Excursion offers a comprehensive taste of Tuscany’s iconic sights and flavors. Priced at $463.14 per person and lasting approximately 9 hours, this tour combines visits to UNESCO-listed Siena and San Gimignano with a relaxing wine tasting experience in the Chianti region. It is ideal for families and small groups seeking a personalized, comfortable day away from crowded city tours.
What makes this experience particularly appealing is the private minivan transport, led by a knowledgeable driver who enhances the trip with warmth and local insights. The tour includes pickup and drop-off inside the port, ensuring easy access, and offers the flexibility to explore at your own pace. While lunch and wine tasting are not included, the visit to a local winery remains a highlight, especially for wine lovers eager to sample renowned Chianti varietals.
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This tour departs directly from Porto di Livorno, Calata Sgarallino, with port pickup and drop-off included. The private minivan provides a smooth, climate-controlled ride between stops, making the entire day stress-free. The driver acts as your guide, providing local knowledge and a welcoming presence, which is often praised in reviews for adding warmth to the experience.

The tour begins at Piazza del Campo, the heart of Siena, where the famous Palio horse race takes place. This UNESCO World Heritage site is a striking shell-shaped plaza lined with medieval buildings. Visitors spend about 40 minutes here, with admission to the square included. It’s a perfect spot to soak in the lively atmosphere and observe the historic setting where Siena’s most famous event occurs.
Next, a brief 20-minute visit to the Duomo di Siena offers views of its stunning facade and intricate interior, although admission tickets are not included. Close by, the Battistero di San Giovanni provides a 10-minute free visit, allowing for quick appreciation of its renowned mosaics and architecture. These sites highlight Siena’s religious and artistic heritage, though some may wish to allocate more time on their own.
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The tour then moves to San Gimignano, often called the “Manhattan of Italy” due to its skyline of medieval tower houses. The 50-minute stop at the 1300 site allows for a leisurely exploration of its cobblestone streets, towers, and scenic views. Admission to San Gimignano is included, giving access to its historic center, which remains a popular photo stop and a chance to wander freely.

A key highlight is the visit to a local winery in the Chianti region. While wine is not included in the tour price, the opportunity to taste different Chianti varietals provides insight into Tuscany’s renowned wine culture. The wine tasting costs an additional 30 euros per person and should be confirmed at the time of reservation. Guests often appreciate the chance to sample authentic wines directly from the source and learn about local production.

This private tour is designed for up to 8 travelers, fostering an intimate atmosphere. The most travelers can participate, and children are welcome provided they are accompanied by an adult. The tour guarantees confirmation at the time of booking, with the flexibility to cancel free of charge up to 24 hours in advance for a full refund.

Although no local guide is included, the driver provides valuable commentary and answers questions during the day. According to feedback, the driver’s warm personality and local insights significantly enhance the experience. The pacing allows enough time for sightseeing and leisure, making the day comfortably enjoyable without feeling rushed.

Most travelers can participate, and the tour is suitable for those comfortable with walking over cobblestone streets and some uneven surfaces. Since transportation is in an air-conditioned minivan, the experience is accessible and comfortable, even during warmer months.

While the $463.14 price covers transportation, site visits, and the convenience of port pickup, the tour does not include meals or wine tasting. Still, the personalized nature, the expert driver, and the visits to Siena and San Gimignano offer a well-rounded day trip. The reviews praise the value for money, especially considering the small group size and flexibility.
This excursion appeals most to those who want an up-close, personalized experience of Tuscany’s highlights in a single day. Ideal for families, small groups, and wine enthusiasts, it offers a balance of cultural exploration, scenic beauty, and wine tasting. Guests seeking a flexible, relaxed pace and a friendly driver typically find this tour rewarding.
The All Tuscany Private Siena San Gimignano & Chianti Livorno Shore Excursion combines the charm of medieval towns with the pleasures of Tuscany’s renowned wines. Its private setup, comfortable transport, and careful itinerary make it a strong choice for cruise visitors looking to maximize their day ashore without feeling rushed.
While it doesn’t include lunch or guided tours, the flexibility and personalized approach compensate. This tour offers a balance of cultural sights and wine tasting, set amidst Tuscany’s iconic landscapes, making it a worthy addition to any cruise itinerary.
“The countryside, towns and winery visit were more than we expected. Our driver/guide, Massimo, AKA Max, was prompt and easy to locate at the port. …”
Is port pickup included?
Yes, the tour includes pickup and drop-off inside Livorno port.
How long does the tour last?
The entire experience lasts approximately 9 hours from start to finish.
Can children participate?
Yes, children are welcome when accompanied by an adult.
Is there a guided tour of Siena?
No, there is no local guide during the visits, but the driver provides commentary, especially at key sites.
Are lunch and wine tasting included?
No, lunch is not included, and wine tasting costs an additional 30 euros per person, payable at the winery.
What is the maximum group size?
Up to 8 travelers can join, ensuring a small-group experience.
How do I confirm my booking?
Booking is confirmed immediately, and cancellation is free up to 24 hours before the tour.
What should I wear?
Comfortable shoes for walking and weather-appropriate clothing are recommended.
Is the tour accessible for mobility-impaired guests?
Most participants can enjoy the tour, but uneven cobblestone streets may pose challenges.
Can I customize the experience?
The tour is fixed in its stops and itinerary; however, the driver’s personalized approach often allows some flexibility.
This tour offers a well-organized, relaxing look at Tuscany’s cultural and culinary treasures, perfect for those wanting a taste of Italy’s medieval charm and renowned wines in a single memorable day.