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

Discover the beauty of Tuscany with a private Brunello di Montalcino wine tour, guided by a knowledgeable sommelier, including scenic drives and wine tastings.

This private tour offers a taste of Tuscany’s most celebrated wine region—Montalcino—paired with breathtaking scenery and the expertise of a local sommelier. It’s an ideal outing for wine enthusiasts craving an authentic experience beyond the bottle, with the chance to visit family-owned wineries, stroll through medieval streets, and capture stunning views of the Val d’Orcia.
What really makes this tour stand out is the combination of personalized attention—thanks to the private setup—and the deep dive into Brunello wine, guided by someone born and raised in the area. The journey promises not just wine tasting, but a full culture, all within a comfortably chauffeured Mercedes van.
One potential consideration is the cost, which might seem high for some travelers, but the quality of the experience, the exclusive access to boutique wineries, and the scenic drives make it well worth the price for many. This tour appeals most to those who love wine, want a relaxed yet informative day, and are eager to enjoy the Tuscan landscape in style.
Wine enthusiasts might appreciate these other Siena tasting experiences

This tour, priced at around $279 per person, offers significant value for those eager to explore Tuscany’s famed wine region with a touch of luxury. Starting from your hotel lobby, you’re whisked away in a private, fully licensed Mercedes van, which promises both comfort and style. With a maximum of about 8 guests, the experience balances privacy with the social aspect of group travel, but it’s ultimately tailored to your needs.
The journey begins with a drive through Val d’Orcia, a landscape so picturesque it’s often seen on postcards or in travel magazines. The rolling hills, medieval towers, and patchwork vineyards create a backdrop that’s both calming and inspiring. Your guide, who speaks both English and Italian, is also your sommelier, adding an educational layer to the trip. They’ll share insights about the region’s history, winemaking traditions, and the nuances of Brunello wines.
Once at the family-owned winery, you’ll appreciate its boutique size—an intimate setting that’s ideal for learning and tasting. The vineyard walk is a highlight, offering a close-up look at the grapes from which Brunello di Montalcino is made. You’ll tour the wine cellar, gaining an understanding of the aging process that defines this wine’s character.
During the tasting, expect at least three different red wines, with some reviews mentioning a tasting of up to four wines. The guide’s expertise shines here, as they explain the differences in flavor profiles, aging, and what makes Brunello unique. Kimberley_E, one of the past reviewers, commented that their guide, Manuele, was “outstanding—very knowledgeable and friendly,” which echoes the general sentiment of personalized, warm service.
After the winery, you’ll have free time to explore the medieval village of Montalcino. It’s the main town of the Brunello area, with well-preserved historic sites, cozy stores, and panoramic viewpoints. Wandering through its narrow streets, you get a real sense of the area’s history and culture. Many visitors mention the town’s picturesque quality, making it an ideal spot for photos and just soaking in the Tuscan atmosphere.

While many wine tours stick to large groups or generic visits, this experience’s private nature ensures you get tailored attention. The guide’s dual role as a sommelier means your tasting isn’t rushed, and you’ll receive plenty of insights into the wines you’re sampling. Plus, because it’s managed by a local born and raised in the region, you gain authentic perspectives behind the name Brunello.
The scenic drive itself is an experience worth the price. The views as you travel through Val d’Orcia are some of the most iconic in Tuscany, and the stops for photographs are a bonus. You can expect to see postcard-worthy landscapes, with rolling hills, cypress trees, and medieval farms.
Timing-wise, the tour starts at 9:30 am, allowing for a full five-hour experience. The pickup is included, which means no stress about navigating or parking—just sit back and enjoy the ride. The vehicle is air-conditioned, ensuring comfort even during warmer months.
Visit durations are flexible; you’ll have time to explore Montalcino at your leisure, perfect for picking up souvenirs or tasting local delicacies. The tour’s cancellation policy is flexible too—free cancellation up to 24 hours before, which is reassuring given plans can sometimes change.

For wine lovers and those seeking an authentic taste of Tuscany, this tour offers a balanced mix of education, indulgence, and scenery. The small group size and personalized guide ensure a genuine experience that’s both informative and fun. The inclusion of boutique wineries means you’re not just tasting mass-produced wine but engaging with producers who are passionate about their craft.
The price reflects what’s included: private transportation, expert guidance, multiple wine tastings, and free time in Montalcino. If you consider the cost per wine and the personalized service, this tour provides considerable value—especially for those who appreciate a relaxed, knowledgeable approach over rushed, large-group excursions.
This experience is perfect for wine enthusiasts, couples celebrating special occasions, or anyone eager to explore Tuscany’s countryside in style. It’s also suitable for those who value local insights and want to learn about Brunello from someone with genuine roots in the area. If you’re after a full day that combines scenic beauty, cultural charm, and exquisite wine, this trip ticks all those boxes.
However, if you’re budget-conscious or prefer larger, more social groups, there are other options out there. But for those looking for a luxurious, intimate, and education-focused experience, this tour hits the sweet spot.

This Brunello di Montalcino wine experience offers a thoughtfully curated day that balances scenic drives, authentic winery visits, and expert guidance. It’s ideal for travelers who want to indulge in Tuscany’s famed wine culture while enjoying the comfort of private transportation and personalized attention. The inclusion of a local guide and sommelier ensures you gain insights that go beyond the labels—adding depth and context to your wine tasting.
While the price might seem on the higher side, the quality of the experience, the beauty of the landscape, and the chance to taste some of Italy’s best wines in an intimate setting justify the investment. It’s a perfect choice for lovers of good wine, scenic views, and genuine local stories.
If you’re after a relaxed, yet enriching day in Tuscany’s heartland, this tour delivers in spades—combining education, indulgence, and a whole lot of Tuscan charm.

Is this tour suitable for non-drinkers?
While the main focus is on wine tasting, non-drinkers can still enjoy the scenic drives, explore Montalcino, and learn from the guide. You can also request alternative options or simply enjoy the scenery.
What is included in the price?
The fee covers private transportation in a fully licensed Mercedes van, pickup from your hotel, an English-speaking guide and sommelier, a vineyard and wine cellar tour, tastings of at least four wines, and free time in Montalcino.
How long does the tour last?
The experience lasts approximately 5 hours, starting at 9:30 am, giving you plenty of time to enjoy each part of the day without feeling rushed.
Can I cancel if my plans change?
Yes, the tour offers free cancellation up to 24 hours before the scheduled start. Cancellations made less than 24 hours in advance won’t be refunded.
Is this tour private or group-based?
It’s a private tour, meaning only your group will participate, which allows for a more personalized and flexible experience.
What is the best time of year to do this tour?
While the tour runs year-round, the best months for scenic drives and outdoor exploring are spring and early fall when the weather is mild and landscapes are especially lush.
Do I need to prepare anything or bring anything?
Comfortable clothing and shoes are recommended, especially if you want to stroll through Montalcino. Bring a camera for those picture-perfect views and perhaps a small bag for souvenirs.
This detailed review hopefully gives you a clear picture of what to expect and helps you decide if this wine journey is right for your Italian adventure.