Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover the private Chianti wine region from Livorno with a personalized 9-hour shore excursion including vineyard visits, medieval town exploration, and optional lunch.

This 9-hour private tour offers an intimate journey into the heart of the Chianti wine region in Tuscany. Priced at $1,025.63 per group for up to 8 people, it provides a personalized experience with air-conditioned transportation, free Wi-Fi, and an English-speaking driver-guide. The tour departs from the Port of Livorno at 9:30 am, with round-trip transfers included, making it a convenient way to explore the scenic countryside and its historic towns during a cruise stop.
What makes this tour stand out is its focus on visiting vineyards for wine tastings, exploring a charming medieval town, and enjoying local Tuscan cuisine — either at a traditional trattoria or a private home (subject to availability). The tour’s high rating of 5.0/5 from 8 reviews confirms its popularity among those seeking a boutique, authentic experience in Tuscany, especially for those who appreciate small-group, tailored guides over generic bus tours.

While in Livorno, here are other experiences we've covered
The tour begins with pickup at the Port of Livorno, specifically at Piazza dell’Arsenale. Departing at 9:30 am, the guide and driver meet your group for a smooth transfer into the Tuscan countryside. The vehicle is air-conditioned, ensuring comfort during the approximately 1.5-hour drive to the first stop. Some vehicles offer free Wi-Fi, which passengers can enjoy while traveling.
This initial pickup is straightforward, and the private transportation means no waiting for large groups or shared buses. It is designed for up to 8 guests, making it ideal for families or small groups seeking a more intimate experience.

The first major stop features a visit to a local winery, either Panzano in Chianti or San Michele a Torri. Here, guests enjoy wine tastings paired with fresh bruschetta after touring the wine cellar. This 1 hour and 30 minutes stop offers a genuine encounter with Chianti’s famous wines.
While admission tickets for the winery are not included, the experience emphasizes tasting Chianti wines directly from the source, allowing for a deeper appreciation of the region’s viticulture. Visitors learn about wine production, and the relaxed setting makes for a memorable tasting.

Following the winery visit, the tour continues with a drive through Montefioralle and Panzano in Chianti. During this approximately 1-hour drive, travelers enjoy views of the vineyards, cypresses, and olive trees that define the famous Chianti landscape.
Montefioralle is a medieval town, known for its historic charm, with narrow streets and ancient stone buildings. This stop allows for photo opportunities and a chance to appreciate the timeless beauty of the Tuscan countryside.

The tour arrives at Greve in Chianti, the heart of Chianti Classico wines. Here, guests have about one hour to stroll around Piazza Matteotti, the town’s central square.
An optional meat tasting at the local butcher shop can be enjoyed along with a glass of wine, giving a taste of local culinary traditions. The free time in Greve offers an authentic feel of this lively town, famous for its wine shops and lively atmosphere.

At lunch time, travelers choose between two options:
– A lunch at a typical Chianti trattoria, featuring local Tuscan dishes at an additional cost.
– A private lunch in a private home, offering an even more personal experience (cost €70 per person, payable in cash on the spot and upon reservation).
This 2-hour break allows guests to enjoy authentic Tuscan cuisine in a charming setting, making the tour not just about sights but also about savoring local flavors.

Returning to Livorno, the final stop is Porto Mediceo, where the round-trip transfer concludes after a 1 hour and 30 minutes drive back. This included part of the tour offers a chance to reflect on the day’s experiences and enjoy the scenic views of the port area.
While the admission to Porto Mediceo is included, the main focus remains on the Chianti countryside, towns, and vineyards.

The tour includes port pickup and drop-off, private transportation, and the air-conditioned vehicle. The driver-guide is English-speaking, providing commentary during the drive through the Tuscan landscape.
Free Wi-Fi is available on most vehicles, though it is not guaranteed on all. The wine tastings cost €30 per person and are paid on the spot. The private home lunch (if reserved) costs €70 per person and is available upon reservation and subject to availability.
While the tour offers a personalized experience, professional guide services for site visits are not included, as drivers are not licensed guides to enter museums or churches. They can provide commentaries from inside the vehicle.
Most travelers can participate, and the tour is designed to be accessible. However, lunch in a private home is subject to availability, and guests should plan accordingly.
The tour is highly rated — 5 out of 5 stars from 8 reviews — highlighting its unique, tailored experiences and stunning countryside views.
This tour suits small groups or families seeking a personalized, relaxed exploration of Tuscany’s most picturesque towns and vineyards. It is ideal for wine lovers, foodies, and those wanting an authentic experience without the crowds of larger buses.
While the tour does not include entry to museums or churches, it offers ample time for sightseeing, tasting, and enjoying the scenery. The private transport and guide ensure a comfortable and flexible pace, perfect for those who value intimate, informative trips.
For a full-day, private exploration of Tuscany’s scenic Chianti region, this tour provides a well-structured itinerary with visits to vineyards, medieval towns, and local markets. The personal touch with a private driver-guide and customizable lunch options makes it stand out among shore excursions.
While some activities, like wine tastings and lunch in a private home, incur extra costs, the overall experience offers genuine cultural and scenic highlights. It is especially suited for those who appreciate personalized service and authentic Tuscan charm.
With excellent reviews, a fixed price, and flexible cancellation, this tour is a trustworthy choice for travelers wanting a comfortable, engaging day in Chianti during their Livorno port visit.
“Felt right at home in the winery and in Florence. We were able to find leather works from the students in Florence. Saw many beautiful sights wit…”
Is pickup available at Livorno Port?
Yes, the tour starts with port pickup and drop-off at Piazza dell’Arsenale.
How long does the tour last?
The entire experience is approximately 9 hours, including all stops and travel time.
Are wine tastings included in the price?
No, wine tastings are not included and cost €30 per person, payable on the spot.
Can I have lunch in a private home?
Yes, private home lunch is available upon reservation for €70 per person, subject to availability.
Is the tour suitable for children or non-drinkers?
Yes, the tour is suitable for most travelers, but alcohol is only served to guests 18+, and site entry is limited to external views.
What is the main highlight of this experience?
The focus is on visiting vineyards, tasting Chianti wines, and exploring medieval towns like Montefioralle and Greve.
Is the transportation comfortable?
Yes, air-conditioned private vehicles are used, with free Wi-Fi on most of them.
Can I customize the itinerary?
The tour is private, allowing some flexibility within the scheduled stops.
Are there any physical limitations I should consider?
The tour is designed to be accessible, but walking in towns or vineyards may require some mobility.
How do I book this tour?
Booking can be done directly through Viator, with full confirmation and free cancellation up to 24 hours in advance.