VIP Brunello Montalcino, Montepulciano & Val d’Orcia with Lunch

A Luxurious Day in Tuscany: VIP Brunello Montalcino, Montepulciano & Val d’Orcia with Lunch

Taking a trip through Tuscany’s rolling hills, vineyards, and medieval towns is a classic adventure for wine lovers and history buffs alike. This small-group tour from Florence offers a way to experience some of the region’s most iconic sights—Montalcino, Montepulciano, and the UNESCO-listed Val d’Orcia—without the hassle of planning. It’s a full day that combines scenic drives, authentic local cuisine, and some of the world’s best wines, notably Brunello di Montalcino.

What we really love about this experience is how smoothly it balances the highlights of Tuscany’s landscape and culture with intimate wine tastings and a delicious homemade lunch. The small-group setup tends to feel more personal and relaxed, giving you space to soak in the views and ask plenty of questions. That said, one thing to consider is the timing—while the tour is well-paced, it requires a full day out from Florence, so it’s best suited for travelers ready for a full immersion in Tuscany’s charm.

This tour is perfect for those looking for a mix of scenic beauty, wine appreciation, and cultural exploration—all wrapped into a seamless, well-organized package. If you’re after a luxurious yet authentic taste of Tuscany’s wine country, this trip has plenty to offer.

Key Points

Small group experience enhances intimacy and interaction.
Brunello di Montalcino is a highlight—considered one of the best wines in the world.
Beautiful scenery of olive groves, vineyards, and classic Tuscan landscapes.
Authentic local food during a guided lunch with wine tastings.
Visits to medieval towns packed with history, charm, and photo opportunities.
Flexible timing for exploring towns and enjoying tastings at your own pace.

In-Depth Look at the Experience

Starting Out: Ease and Comfort from Florence

The tour begins at 8:30 a.m. from the centrally located Starhotels Michelangelo in Florence. The vehicle used is a private, comfortable transport, ideal for a smooth ride through Tuscany’s scenic roads. We found that group sizes are kept intimate—max of six travelers—which makes for a more personalized experience.

The drive from Florence to Chianti’s picturesque hills feels like peeling through a living postcard. We loved the way Morad, the guide, narrated stories about the landscape and towns, making the scenery even more engaging. The short stop in Monteriggioni, a fortified medieval castle from 1213, offers a quick but compelling glimpse into Tuscany’s storied past and provides great photo opportunities.

First Stop: Montalcino and Its Fortified Charm

Arriving in Montalcino, the feeling of stepping back in time hits immediately. This medieval village is renowned for its fortress, surrounded by boundary walls and towers. The fortress, with its commanding 14th-century structure, offers jaw-dropping views of the Val d’Orcia, renowned for its breathtaking, postcard-perfect scenery.

Wandering through Montalcino’s narrow streets, you’ll find dozens of wineries and artisan shops selling local products—think cheese, cured meats, and crafts. One of the tour’s standout moments is the visit to a historic farm, where a guided lunch-tasting awaits. Here, you’ll sip on Rosso di Montalcino and the prestigious Brunello di Montalcino, both served alongside a selection of typical Tuscan delicacies. Reviewers rave about the quality of the lunch and the wine; Jason_W called it a “fantastic trip,” highlighting the small winery’s amazing Brunello and the delicious homemade dessert.

The Best of Val d’Orcia’s Scenery

Next, the tour takes you to the UNESCO World Heritage site of Val d’Orcia. Known for its rolling hills, cypress-lined roads, and harmonious landscape, it’s an area that has inspired painters and photographers for centuries. Here, you’ll stop for 15 minutes to take in panoramic views, snap photos, and breathe in the fresh Tuscan air.

Travelers like Julia_R appreciated the chance to see the landscape without crowds, noting that it felt like a private experience. The scenery is truly what makes this region special—think of the sweeping vistas that look like they belong on a postcard, dotted with castles, churches, and harbors of old Etruscan villages.

The Charm of Montepulciano

The final stop of the day is Montepulciano, perched atop a hill 600 meters above sea level. Enclosed by fortified walls, it’s a town known for its noble wines and Renaissance architecture. The narrow, steep streets invite exploration—perfect for wandering at your own pace.

You can opt for a wine tasting in Montepulciano’s historic cellars, which many guests find memorable. The town itself is a treasure trove of Renaissance palaces, and the views from its vantage points are spectacular. Reviewers like Leah_P described Montepulciano as “beautiful,” with charming streets and impressive architecture. You’ll have about an hour and a half here, enough time to soak in the atmosphere, visit a wine cellar, and take some photos.

Practical Details and Value

The entire day lasts roughly 9 to 10 hours, making it a full-day adventure. The tour is priced at around $231 per person, which includes transportation, expert guiding, tastings, and a homemade Tuscan lunch. Considering the private winery visit, multiple scenic stops, and the personalized small-group experience, many travelers feel it’s excellent value.

Morad, the guide, receives high praise for his knowledge and friendly demeanor. Reviewers note how he shares interesting facts about the towns, wines, and landscape—adding depth to the experience. One reviewer appreciated that Morad was always attentive, stopping for photos upon request, although a few mentioned that he sometimes checked his phone during drives—something to keep in mind if you value undivided attention.

The Experience’s Strengths and Considerations

The standout features are undeniably the stunning scenery, authentic wine tastings, and personalized guidance. Many reviews highlight how the small group felt like a private tour, allowing for more relaxed conversations and a more tailored experience. The lunch, featuring local produce and homemade desserts, complements the wine tastings perfectly, giving you a true taste of Tuscany.

However, it’s a full-day commitment. If you’re not used to long tours or prefer a more relaxed pace, this might demand some energy. Also, for those with mobility issues, the steep streets in towns like Montepulciano could pose a challenge.

Who Will Love This Tour?

This VIP experience suits travelers eager to combine scenic beauty, cultural charm, and wine tasting in an organized, intimate setting. It’s ideal for those who want to avoid the hassle of planning and prefer guided insights from knowledgeable hosts. The focus on Brunello di Montalcino makes it perfect for wine enthusiasts wanting to sample one of Italy’s most prestigious wines, while the small group ensures you won’t feel like just another face in a crowd.

If you’re after a day of picturesque views, delicious food, and expert commentary in a luxe setting, this tour ticks all the boxes. It’s also a great choice if you’re visiting Florence and want a comprehensive yet manageable taste of Tuscany’s best.

Frequently Asked Questions

How long is the tour?
The tour lasts approximately 9 to 10 hours, starting at 8:30 a.m. and returning to Florence in the evening.

What’s included in the price?
The price covers transportation in a comfortable vehicle, guided visits, wine tastings, and a homemade Tuscan lunch with local products.

Is this tour suitable for small groups?
Yes, the tour is limited to a maximum of six travelers, providing an intimate, personalized experience.

Can I taste Brunello di Montalcino?
Absolutely. The tour includes a tasting of Brunello di Montalcino, considered one of the world’s finest wines.

Is there free time at each stop?
Yes, at Montalcino and Montepulciano, you’ll have time to explore on your own, visit wine cellars, and take photos.

Are the towns accessible for people with mobility issues?
The towns feature steep streets and uneven surfaces, so mobility might be a consideration.

What kind of food is served during lunch?
A guided lunch with local produce, including a homemade dessert, is served at a historic farm in Montalcino.

Can I book a wine tasting in Montepulciano?
Yes, there’s an option to enjoy a tasting in Montepulciano after some free time.

Is there a cancellation policy?
Yes, free cancellation is available up to 24 hours before the start time, with full refunds.

In the end, this tour is a fantastic way to experience Tuscany’s legendary landscapes, wines, and towns—all in a relaxed, small-group setting. Whether you’re a wine connoisseur, a lover of medieval towns, or someone simply seeking a curated taste of Italy’s countryside, this experience offers a well-rounded, memorable day. The high praise from previous guests reflects its quality, especially the knowledgeable guides and the authenticity of the tastings and scenery. Just bring your camera, comfortable shoes, and a good appetite for an unforgettable Tuscan adventure.