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Experience Tuscany’s finest wines on this small-group Brunello and Chianti tasting tour from San Gimignano, including hotel pickup, expert guides, and scenic views.

This 6.5-hour small-group tour in Tuscany offers a chance to explore the renowned Brunello di Montalcino and Chianti wine regions, with hotel pickup and drop-off included. Priced at $137.75 per person, it is designed for those eager to taste top-tier wines while soaking up the scenic landscapes and historic towns of Tuscany. With an average booking time of 81 days in advance, it appeals to travelers planning their trip ahead. The tour is limited to 8 participants, providing a more intimate experience and personalized attention from multilingual guides.
What makes this tour stand out is its focus on prestigious wineries praised in specialized magazines, plus the opportunity to walk through Montalcino’s historic fortress and visit famous wine shops. While the transport involves a significant amount of driving, the scenic countryside and quality of wine tastings make it a worthwhile experience for wine lovers and culture seekers alike.

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The tour begins with a scenic journey from San Gimignano, traveling by air-conditioned minivan or minibus through the lush Tuscan landscape. The vehicles comfortably accommodate up to 8 or 20 people, providing a relaxed atmosphere for the drive. The countryside is dotted with rolling hills, vineyards, and picturesque villages, setting the perfect mood for tasting some of Italy’s most celebrated wines.
This drive is a highlight for those who appreciate the natural beauty of Tuscany, though it does involve a fair amount of travel time. Several reviews note that most of the day is spent in transit, with around 4 hours of driving overall. It’s worth preparing with snacks and water, as no refreshments are provided in the vehicle during the long hours on the road.

A significant part of the tour is the visit to Montalcino, a charming hilltop town famous for Brunello di Montalcino. Travelers walk through its narrow streets and visit the centuries-old fortress, which offers a glimpse of the town’s historic architecture and panoramic views of the surrounding landscape.
In Montalcino, you will have free time to explore at your own pace. The town’s stunning vistas and well-preserved medieval structures make for great photo opportunities. The local atmosphere adds to the experience, giving visitors a sense of the region’s deep wine-making roots and architectural heritage.

The core of this experience is the wine tastings at prestigious local wineries. The tour includes two tastings, each offering a diverse selection of Tuscan wines, with an emphasis on Brunello di Montalcino. The first tasting is described as delightful, with a focus on quality and flavor, while the second can feel more like a wine shop visit, according to some reviews.
The wineries praised in specialized magazines ensure that visitors get a chance to sample top-tier wines, often with the guidance of knowledgeable staff. The wine tasting experience is complemented by snacks like olive oil and bruschetta, enhancing the tasting notes and overall enjoyment.

Brunello di Montalcino is made from Sangiovese grapes and is celebrated worldwide for its complexity and aging potential. The wines from this region embody centuries of winemaking tradition passed down through generations. The tour offers an opportunity to sample these prestigious wines and learn about their unique production process from experts.
In addition, the tour covers Chianti, another iconic Tuscan wine region, providing a broader taste of Tuscany’s rich winemaking landscape. The variety of wines sampled reflects the diverse flavors and styles associated with these renowned regions.
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The small group size ensures a more personalized experience, with the minivan or minibus providing comfortable transport. The tour is designed for up to 8 travelers, which allows guides to give more detailed explanations and attention.
Pickup and drop-off are included, with the meeting point at Porta San Giovanni in San Gimignano. If your hotel is inside the walls of San Gimignano, the pickup might be just outside Porta San Giovanni.

Reviewers mention that most of the day is spent in the vehicle, so bringing snacks and water is recommended, especially since no in-car refreshments are provided. The tour does require participants to be able to climb and descend stairs, which is worth considering if mobility is limited.
It’s also advisable to book early, as the tour is popular and typically reserved 81 days in advance. While the price of $137.75 offers good value considering the hotel transfers and tastings, some guests find the long driving times a bit tiring and suggest that future tours could be shortened.

This experience suits wine enthusiasts eager to taste prestigious Tuscan wines, especially Brunello di Montalcino. It also appeals to those interested in historic towns and scenic drives through Tuscany’s landscapes. Couples, small groups, and solo travelers seeking a more intimate setting will find this tour particularly enjoyable.
However, travelers should be prepared for a lot of driving and long hours on the road. If physical mobility is a concern, or if more in-depth winery visits are preferred, it’s worth considering alternative options.
This small-group tour offers a convenient way to explore Montalcino’s historic charms and taste some of Italy’s most esteemed wines. The inclusion of hotel pickup and round-trip transport adds to its convenience, making it accessible even for those unfamiliar with local logistics.
While some reviews mention long travel times and the absence of in-vehicle refreshments, the quality of wine tastings and the expert guides balance these aspects well. The limited group size ensures a more personalized experience, especially during the tastings and exploration of Montalcino.
This tour provides a solid introduction to Tuscany’s wine culture for those willing to spend a day on the road, with the reward of exceptional wines and scenic views.
“What a great experience! Vincenzo was so informative and a great driver for the day. We experienced vineyards so unexpected and one trip to remembe…”
Is hotel pickup included?
Yes, hotel pickup and drop-off are included in the tour price, with departure from Porta San Giovanni in San Gimignano.
How many wineries are visited?
The tour includes two wine tastings at prestigious wineries praised in specialized magazines.
What wines are sampled?
Guests taste Brunello di Montalcino and Chianti wines, with the focus on high-quality, renowned varieties.
How long is the total drive time?
There is approximately 4 hours of driving overall, with most of the day spent traveling between stops.
Is food provided during the tour?
No, lunch is not included, but snacks like olive oil and bruschetta are served during tastings.
What is the group size limit?
The tour is limited to 8 travelers for a more intimate experience.
Can I cancel the tour?
Yes, full refunds are available if canceled at least 24 hours in advance.
Are children allowed?
Most travelers can participate, but participants need to be able to climb and descend stairs.
What should I bring?
Bring snacks, water, and comfortable shoes for walking around Montalcino.
Is this tour suitable for non-wine drinkers?
The focus is on wine tastings, so it is best suited for those interested in wine experiences.