Florence: Montalcino, Montepulciano & Val d Orcia with lunch

If you’re dreaming of soaking in the rolling hills, timeless villages, and world-renowned wines of Tuscany, this tour offers a compelling way to do it without the hassle of planning every detail yourself. While we haven’t personally taken this specific trip, the glowing reviews and detailed itinerary paint a picture of a well-curated experience that lets you enjoy the best slices of this legendary region.

What really catches our eye about this tour is how it combines delightful small-group intimacy with the chance to visit iconic towns like Montalcino and Montepulciano, along with the stunning landscapes of the Val d’Orcia. The inclusion of guided wine tastings and a traditional Tuscan lunch makes this more than just sightseeing—it’s a taste of local life and flavors. On the flip side, the full day is quite packed, and those with mobility issues might want to consider the walking involved.

All in all, this trip seems ideally suited for travelers who want a deep yet manageable dive into Tuscany’s highlights in a friendly, relaxed setting. If you love wine, picturesque scenery, and charming towns, you’ll likely find this tour hits the spot. But if you’re after a more relaxed day or traveling with very young children, you might want to weigh the intensity of a 10-hour journey.

Key Points

• Small-group experience with personalized attention and fewer crowds
• Expert guide known for being knowledgeable and friendly
• Includes an authentic Tuscan lunch paired with wine tastings
• Visits to iconic towns like Montalcino and Montepulciano with free time to explore
• Breathtaking landscapes of the Val d’Orcia and Chianti regions
• Ideal for wine lovers and those keen to see Tuscany’s most photogenic spots

You can check availability for your dates here:

A Taste of Tuscany: What the Tour Offers

This trip is a full-day journey into the heart of Tuscany that balances guided visits with leisure time, scenic drives, and delicious tastings. It’s designed to showcase the region’s medieval villages, UNESCO-worthy landscapes, and world-class wines—and it does so with an emphasis on quality and comfort.

Departure and Structure

The tour departs from Florence, with the meeting point conveniently located in front of Starhotels Michelangelo. It runs about 10 hours, so you’ll want to set aside the entire day for travel, exploration, and relaxation. The group is limited to just 6 participants, which means more personalized attention from your guide and a chance to ask questions or customize your experience a bit.

Transportation and Timing

Traveling in a small, comfortable vehicle, you’ll cruise through Tuscany’s signature scenery—hills dotted with vineyards, olive groves, and medieval fortresses. The schedule is tight enough to see a lot but not so rushed that you’ll miss the details. The small group size also means you’ll get more flexibility and a less touristy feel.

Visiting Montalcino: Wine and History

Montalcino, famous for its Brunello di Montalcino, is a highlight of the day. The visit to a boutique winery-farm offers a guided tasting of Brunello and Rosso di Montalcino, with the chance to learn about the wine-making process directly from the experts. The included lunch, featuring local products and a homemade dessert, pairs perfectly with the wines, making this stop a real treat.

Reviewers keep mentioning how much they appreciated the “knowledgeable and friendly” guide, Morad, who ensured everyone understood the significance of each wine and was attentive to the group’s pace. The guided tasting at the winery, combined with the opportunity to explore the farm and its surroundings, makes this more than just a quick wine sample—it’s an immersive experience.

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Pros and Cons

While the winery visit is a definite highlight and good value for wine aficionados, those who aren’t particularly interested in wine might find it a bit focused on tasting. However, even casual drinkers will enjoy learning about the region’s proud winemaking tradition and sampling some excellent wines.

Exploring Montepulciano: Renaissance Charm

Perched atop a hill 600 meters above sea level, Montepulciano is famous for its noble Vino Nobile wine and beautifully preserved Renaissance architecture. After a drive on a scenic route, you arrive with free time to stroll the steep streets, visit local wine cellars, or just soak in the view of the surrounding countryside.

The reviews praise the town’s authentic atmosphere and highlight how the small group allows for more flexible exploration—whether wandering through narrow alleyways, sneaking into a cellar, or snapping photos of the landscape.

For those interested in wine, there’s an optional extra: a second wine tasting in Montepulciano, which some travelers opt for to deepen their appreciation of this historic town’s viticultural heritage.

The Scenic Val d’Orcia

Most travelers agree that the Val d’Orcia is the true star of the landscape. Recognized as a UNESCO site, these rolling hills dotted with cypress trees, castles, and ancient villages are picture-perfect. Films like Gladiator have made this scenery famous, and it’s easy to see why.

The tour makes a stop to take in the views, perfect for photos and just appreciating how natural and human effort have shaped this landscape. Many reviews mention how the vast, undisturbed beauty of the hills made a lasting impression.

Practical Details

The tour includes all transportation, guided commentary, wine tastings, and lunch, making it a solid package for the price. The small group limit — only 6 participants — creates a more personal experience, but it also means spots can sell out fast, so booking ahead is wise.

What to Bring

Comfortable walking shoes are a must, as both towns involve some uneven streets and a bit of uphill walking. A sun hat, sunscreen, and water are recommended, especially in warmer months. Don’t forget your camera—these landscapes and towns are insanely photogenic.

Not Suitable For

This experience isn’t recommended for children under 10, pregnant women, or people with mobility issues, as the terrain and walking involved can be challenging.

Real Traveler Insights

Reviews highlight how much guests appreciated the expert guide’s knowledge and the unhurried pace. One reviewer called Morad “very attentive and a good driver,” noting that the guide’s calm approach made the day smooth and enjoyable. Several praised the delicious lunch and excellent wine, calling it “the best experience of this kind” they’ve had.

Others mentioned how the stunning scenery and opportunity for free exploration made the experience feel personalized and special. The combination of historic towns, scenic drives, and wine tasting seems to hit the right note for most travelers.

Final Thoughts

This tour offers a well-rounded taste of Tuscany’s most iconic sights, paired with memorable local flavors. It’s a good choice for those wanting an all-inclusive, guided experience that minimizes stress but maximizes discovery. The focus on small group size and knowledgeable guides ensures you won’t feel lost in a crowd, and the visits to Montalcino and Montepulciano are highlights that many find worthwhile.

While it’s a full day, the carefully curated stops and the variety of landscapes—from medieval villages to rolling hills—make it feel like a true journey through Tuscany.

If you’re passionate about wine, enjoy scenic drives, and want to experience Tuscany without the hassle of organizing every detail, this tour could be just right. But if you prefer a more relaxed pace or are traveling with very young children, you might want to consider something more flexible.

FAQ

Is transportation included? Yes, transportation in a small, comfortable vehicle is part of the package, making it easy to relax and enjoy the scenery.

How long is the tour? The tour lasts about 10 hours, from the meeting point in Florence to the return.

What should I bring? Comfortable shoes, sun protection, a camera, water, and a hat are recommended for a comfortable day.

Can I customize the experience? The small group size and flexible schedule allow for some personal touches, like optional additional wine tastings.

Is this tour suitable for children? No, it’s not recommended for children under 10, as the walking and activities may be challenging.

Do I need to pay in advance? You can reserve your spot now and pay later, with free cancellation up to 24 hours before the tour.

What kind of wines will I taste? Expect to sample Brunello di Montalcino, Rosso di Montalcino, and Vino Nobile di Montepulciano.

Is the lunch included? Yes, a guided Tuscan lunch with local products and homemade dessert is part of the experience.

How much free time do I get in each town? You’ll have enough time to explore the towns at your pace—enough for photos, a quick walk, or a visit to a local shop.

Will the scenery be as beautiful as in photos? Absolutely. Guests consistently mention how breathtaking the views are, especially in the Val d’Orcia.

To sum it up, this tour is a solid pick for anyone who wants to experience the quintessential Tuscan landscape, taste authentic wines, and explore charming villages—all in a manageable, well-organized day. It’s perfect for travelers who appreciate good company, expert guidance, and a taste of Italy’s finest.

You can check availability for your dates here: