Florence: Montalcino, Montepulciano & Val d Orcia with lunch

Discover the beauty of Tuscany on this 10-hour small-group tour that takes you through Montalcino, Montepulciano, and the stunning Val d’Orcia. Led by an expert English-speaking guide, this experience offers a perfect blend of scenic drives, historical towns, and exclusive wine tastings, all within a limited group of just 6 participants. The tour includes a guided wine tasting at a boutique Montalcino winery and a lunch featuring local products and Brunello di Montalcino wines.

This tour is ideal for those seeking a rich taste of Tuscany’s landscapes, wine culture, and charming villages without the hustle of larger groups. While the full-day experience covers a lot of ground, it’s well-paced and balanced between sightseeing, tasting, and free time. Expect breathtaking views, authentic food, and a chance to learn about Tuscany’s winemaking traditions — making it suitable for anyone who appreciates high-quality wine, history, and scenic landscapes.

Key Points

• Duration: 10 hours from Florence, with a small group of up to 6 participants
• Highlights: Montalcino boutique winery, Montepulciano town, UNESCO-listed Val d’Orcia, and panoramic Tuscany views
• Wine tasting: Guided tasting of Brunello di Montalcino and Rosso di Montalcino at a historic farm
• Lunch: An included gourmet meal with local products, wines, and homemade dessert
• Flexible options: Opportunity to add a second wine tasting in Montepulciano
• Meeting point: Front of Starhotels Michelangelo, Florence

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Discover Montalcino’s Boutique Winery and Brunello Tasting

The tour begins with a visit to a small, boutique winery-farm in Montalcino. Here, a guided tasting introduces you to Brunello di Montalcino, a renowned DOCG wine, along with Rosso di Montalcino. The estate’s historic setting adds a special touch to the tasting, and you have time to explore the cellars and enjoy the natural scenery surrounding the farm.

The guide provides insight into the winemaking process and local traditions, making the experience both educational and enjoyable. After the tasting, a delicious lunch is served, featuring local products, wines, and a homemade dessert. The meal complements the wines and offers a taste of regional flavors in a scenic setting.

Scenic Drive through the Val d’Orcia, a UNESCO World Heritage Site

Following the Montalcino visit, the tour takes you through the Val d’Orcia, a landscape famous for its rolling hills, cypress trees, and historic farms. This area’s extraordinary scenery has been featured in movies like Gladiator.

A stop in the UNESCO-listed valley allows you to admire the harmony of nature and human craftsmanship, with views that seem straight out of a postcard. The landscape here is known for its perfectly shaped hills and iconic cypress-lined roads, offering photo opportunities and moments of tranquility.

Exploring the Medieval Charm of Montepulciano

Next, the journey leads you to Montepulciano, a hilltop town perched at 600 meters above sea level. Enclosed by fortified walls, the town boasts Renaissance architecture, narrow steep streets, and historic wine cellars.

You have free time to wander, exploring the Renaissance palaces, cathedral, and local shops. The town’s reputation for noble wine from surrounding vineyards makes it a perfect spot for wine lovers. Travelers can choose to add a second winery visit and enjoy an additional tasting, deepening their appreciation for Montepulciano’s wine culture.

The Tour Includes a Panoramic Scenic Drive

A highlight of this tour is the panoramic road that connects the towns and landscapes. This drive offers unforgettable views of Tuscan hills, vineyards, and ancient villages. Travelling by comfortable vehicle, you can relax and soak in the picturesque scenery that defines Tuscany.

The route is designed to give plenty of photo stops and moments to enjoy the natural beauty of the region. The drive itself becomes a highlight, showcasing green expanses, cypress-lined roads, and historic castles and farms along the way.

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Small Group Experience with Expert Guidance

This tour is limited to just 6 participants, creating an intimate setting that allows for personalized attention and flexibility. The English-speaking guide, Morad, receives high praise for being knowledgeable, friendly, and attentive.

Guests appreciate the calm pace, the respect for time at each stop, and the ability to ask questions. The small group size ensures a more relaxed atmosphere and better opportunities for personalized experiences like exploring towns at your own pace or enjoying additional tastings.

Practical Details: Meeting Point and What to Bring

The tour departs from in front of Starhotels Michelangelo in Florence, at coordinates 43.77671432495117, 11.238204956054688. It is advisable to wear comfortable walking shoes, bring a sun hat and sunscreen for outdoor activities, and carry a camera to capture the scenic views.

Participants should also bring water to stay hydrated, especially during warmer months. The tour does not allow smoking, and it is not suitable for children under 10, pregnant women, or those with mobility issues.

What Sets This Tour Apart from Similar Options

Compared to other Tuscany tours, this experience emphasizes small-group intimacy, quality wine tastings, and exclusive visits to boutique wineries. The inclusion of a gourmet lunch with local products and the chance to explore historic towns at leisure adds significant value.

The tour’s focus on the Val d’Orcia’s UNESCO scenery and the historic charm of Montepulciano makes it particularly attractive for photo enthusiasts and wine lovers alike. Its relaxed pace and expert guidance stand out among similar full-day trips.

The Sum Up: A Taste of Tuscany’s Best in a Small Group

This 10-hour tour offers a well-rounded experience of Tuscany’s wine, landscapes, and historic villages. The boutique winery visit in Montalcino and the free time in Montepulciano are highlights, as is the stunning scenery of the Val d’Orcia.

Thanks to its small group size and knowledgeable guide, the experience feels personalized and authentic. It’s especially suited for those who want quality over quantity — enjoying delicious wines, beautiful views, and charming towns without feeling rushed.

While the full-day pace includes many stops, the carefully curated itinerary ensures you get plenty of time to relax, explore, and savor Tuscany’s most celebrated sights and tastes.

Frequently Asked Questions

What is included in the tour price?
The tour covers transportation, a guided wine tasting at a boutique winery, and a gourmet lunch with local products and wines.

How long is the tour?
The tour lasts approximately 10 hours, starting and ending in Florence.

Where does the tour meet?
The meeting point is in front of Starhotels Michelangelo in Florence, with specific coordinates provided.

Is this tour suitable for children?
No, it is not suitable for children under 10 years.

Can I add an extra wine tasting?
Yes, there is an option to add a second winery in Montepulciano for an additional wine tasting.

What should I bring?
Participants should bring comfortable shoes, sun protection, a camera, water, and dress appropriately for the weather.

Is the tour wheelchair accessible?
No, it is not suitable for people with mobility impairments or wheelchair users.

What makes this tour different from other Tuscany excursions?
This tour emphasizes small-group experience, personalized guidance, and exclusive visits, offering a more intimate and detailed look at Tuscany’s wine and scenery.

How is the guide?
Guests praise Morad for being knowledgeable, friendly, and attentive, making the experience engaging and informative.

Can I expect free time in the towns?
Yes, the itinerary allows free time in Montepulciano and Montalcino for exploring at your own pace.

This tour stands out as a perfect choice for wine enthusiasts and lovers of scenic Tuscany, offering a rich, relaxed day filled with beautiful views, delicious local food, and excellent wines in a small, friendly group.

You can check availability for your dates here: More Great Tours Nearby