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

Discover Chianti's medieval villages with a private tour in an open-top minivan, including lunch, wine tasting, and visits to Montefioralle, Piazza Matteotti, and Castellina in Chianti.
Exploring Tuscany’s famed Chianti region becomes a memorable experience with the Villages of Chianti with lunch and tasting in an Open Top Van tour. Priced at $247.76 per person, this private adventure lasts around 7 to 8 hours, offering a relaxed yet comprehensive look at some of the most charming medieval villages. Departing from Florence, the tour is perfect for visitors who appreciate personalized experiences, thanks to its exclusive group size and specially modified open-top minivan that highlights the scenic landscapes.
This tour stands out because it combines cultural visits, such as walks through ancient streets, with a delicious Tuscan lunch paired with local wines. The last stop provides an excellent opportunity to purchase and ship bottles directly from the producers, adding a practical touch to the day. While hotel pickup and drop-off are not included, the meeting point is conveniently located in Florence, and the tour begins at 9:30 am.


The tour begins at Castello di Montefioralle, a classic Tuscan hill town encased by its original medieval walls. Visitors are free to explore for 30 minutes, wandering through this well-preserved site that offers a glimpse into Tuscany’s past. Admission is free, allowing you to appreciate its authenticity without extra costs. The village’s narrow streets and stone houses provide fantastic photo opportunities, making it a perfect first stop to set the tone for the day.
Montefioralle remains largely unchanged, giving you a real sense of stepping back in time. It’s ideal for those interested in history or simply looking to soak in the peaceful atmosphere of a medieval village. Since there’s no entry fee, the focus stays on enjoying the scenic surroundings and architectural details.
Keen to taste more of Florence? We've looked into these other food and drink experiences
Next, the tour moves to Piazza Matteotti, a lively and picturesque town square. Here, visitors spend 30 minutes browsing the charming arcades and craft shops that showcase local products. The square’s vibrant environment offers a taste of daily Tuscan life, with artisans selling handmade goods and regional delicacies.
The open-air market vibe makes it easy to relax and take photos. The free admission allows ample time for wandering and sampling small local treats, giving a glimpse of authentic Tuscan community life. This stop pairs well with the scenic drive, providing a break from sightseeing with a chance to enjoy the local atmosphere.

The day continues with a 35-minute visit to Castellina in Chianti, a medieval village dating back to the 1200s. Walk the ancient streets lined with shops, cafes, and historical sites. This village’s enduring architecture and old-world charm make it a highlight of the tour.
Visitors can appreciate the sense of history as they explore the narrow alleys and local landmarks. Since admission is free, there’s flexibility to soak up the ambiance at a relaxed pace. Castellina in Chianti offers the chance to connect with Tuscany’s medieval roots while enjoying the peaceful environment of a small Chianti town.

One of the key highlights of this tour is the 2-hour stop for an authentic Tuscan lunch paired with wine tastings. The guided winery tour provides insights into local wine production, and the meal itself showcases regional dishes made with fresh ingredients.
Guests have the chance to sample select wines directly from the producer, with a subsequent option to purchase and ship bottles. This combined experience of food, wine, and local craftsmanship offers a well-rounded taste of Tuscany’s culinary culture. The setting typically adds to the charm, often in a scenic vineyard or winery estate, making this meal a memorable part of the day.

A distinctive feature of this tour is the specially modified open-top minivan, which enhances the sightseeing experience. This vehicle allows unobstructed views of the rolling Tuscan hills, vineyards, and olive groves as the group travels between stops.
The design ensures that guests can fully appreciate the landscape, making the journey as engaging as the destinations themselves. The open-top setup also makes photo opportunities easy and enjoyable, especially on clear weather days. This vehicle choice sets the tour apart from standard coach trips, offering a more intimate and scenic exploration.
While in Florence, here are other experiences we've covered

The final part of the tour takes advantage of the opportunity to buy wines directly from the producer. Guests can select bottles during the visit, then arrange for them to be shipped home, which is especially convenient for those traveling lighter or wanting to bring back authentic Tuscan wines.
This practical aspect ensures that the experience extends beyond the day’s sightseeing, giving a tangible keepsake of the trip. The ability to purchase and ship wines adds a layer of value, especially for wine enthusiasts seeking quality bottles straight from the source.

This private tour departs from Florence at 9:30 am from Via dei Renai, 5. It is designed for groups of most travelers, with confirmation received immediately upon booking. Since the tour is private, only your group participates, allowing for a flexible and personalized experience.
While hotel pickup and drop-off are not included, the centrally located meeting point makes it easy to access via public transport or taxi. The tour concludes back at the starting location, providing a straightforward end to the day.

The five-star rating and glowing reviews highlight the tour’s quality and the memorable experience it provides. Visitors praise the knowledgeable guides, the excellent selection of wines, and the relaxed pace that makes exploring Tuscany’s villages enjoyable.
The tour is particularly suited for those who want a personalized experience beyond large group excursions, with the added bonus of a scenic drive in a specially designed vehicle. If you appreciate good food, wine, and authentic villages, this trip offers a well-balanced mix of all three.
This private tour combines heritage, gastronomy, and scenic beauty in a compact, carefully curated package. The carefully chosen stops at Montefioralle, Piazza Matteotti, and Castellina in Chianti showcase the diversity of Tuscan small towns. The lunch and wine tasting add a culinary dimension to the experience, making it ideal for those wanting to indulge in local flavors.
The special open-top minivan is a highlight, providing excellent views and a comfortable way to enjoy Tuscany’s landscapes. The opportunity to buy wines directly from producers makes this tour especially appealing for wine lovers.
While hotel pickup is not included, the centrally located meeting point and the private nature of the tour ensure a smooth, intimate, and relaxing day in Chianti. This experience is best suited for visitors seeking a personalized, scenic, and gastronomic journey through Tuscany.
“My husband and I booked this tour for our honeymoon and it was to date one of the best days of our lives. We absolutely loved everything about the…”
Is hotel pickup included in this tour?
No, hotel pickup and drop-off are not included. The tour starts at Via dei Renai, 5, Florence.
What is the duration of the tour?
The tour lasts approximately 7 to 8 hours.
Can I purchase wines during the tour?
Yes, the last stop offers the chance to buy wines directly from the producer and ship them home.
Is this tour suitable for children or people with mobility issues?
Most travelers can participate, but the tour involves walking through medieval villages, which may include uneven surfaces.
What makes this tour unique?
The specially modified open-top minivan provides exceptional views, and the private setting ensures a relaxed experience.
Are meals included?
Yes, a traditional Tuscan lunch with wine tasting at a winery is included in the 2-hour stop.
What is the price per person?
The tour costs $247.76, offering a comprehensive experience in Chianti.
How far in advance should I book?
On average, the tour is booked about 100 days in advance.