Two days of Tuscany discovering the Nobile, Brunello, Chianti area

A Two-Day Journey Through Tuscany’s Iconic Wine and Historic Villages

This tour promises an authentic taste of Tuscany, focusing on its celebrated Nobile, Brunello, and Chianti wines, along with visits to some of the region’s most charming towns. It’s tailored for those who want to experience the essence of Tuscany without the hassle of planning, thanks to private transportation and expert guides. While the price might seem steep at over $1,000 per person, the included wine tastings, guided visits, and overnight stay in an agriturismo make this a worthwhile investment for wine lovers and culture seekers alike.

What we particularly appreciate about this experience is the personalized approach — from the private driver to the customized itinerary, you won’t feel like just another tourist. A potential consideration is the pace of the schedule, which involves a lot of moving around, so those with mobility challenges should consider this. This tour suits travelers eager to dive into Tuscany’s wine heritage, picturesque towns, and scenic vistas—especially if you value comfort and expert insights along the way.

Key Points

• Intimate and personalized experience with a private driver and small group size.
• Expert guides who bring local history and wine production to life.
• Visit iconic hill towns like Montepulciano, Pienza, Montalcino, Siena, San Gimignano, and Castellina.
• Tastings of renowned wines like Brunello, Vino Nobile, Chianti, and Supertuscan.
• Includes all fees, taxes, and accommodations for a hassle-free trip.
• Flexible and well-structured itinerary blending culture, history, and wine.

An In-Depth Look at the Itinerary

Day 1: The Heart of Val D’Orcia and Montalcino

The journey kicks off in Florence at 8:30 am, with a private, air-conditioned vehicle ready to whisk you away. Starting with Piazza Grande in Montepulciano, you’ll get an immersive hour and a half exploring the town’s main square, with its impressive Duomo and historic palaces like Contucci and Tarugi. This is the perfect introduction to the region’s medieval architecture and lively atmosphere. The fact that the visit is free and flexible allows you to soak in the ambiance at your own pace.

Next, a quick stop at Contucci Cantine offers an opportunity to sample Nobile di Montepulciano in the very cellars where the wine ages. The guide’s insights about how Sangiovese grapes are transformed into this distinctive wine deepen the tasting experience. One reviewer mentioned that the guide, Mario, was especially knowledgeable and made the visit memorable, customizing the day to fit their interests.

Following this, you’ll visit Pienza, the “ideal city of the Renaissance,” with stunning views of the Val D’Orcia valley. Its compact historic center offers photo-worthy vistas and a chance to stroll through quaint streets, imagining the town’s Renaissance heyday.

The afternoon continues with Montalcino, the legendary home of Brunello. Here, you’ll explore the Fortezza, the town’s fortress, and learn about the history of Brunello wine. The highlight is the visit to Piombaia wine cellar, where you’ll taste Brunello, Montalcino Rosso, and wines from Sant’Antimo. A reviewer praised the included tasting, noting how the guide explained the Sangiovese grapes’ role in Brunello’s production, adding depth to the experience.

Day 2: Siena, San Gimignano, and Chianti

Day two begins in Siena, famous for its Duomo and the lively Piazza Il Campo. With tickets included, you’re free to admire the cathedral’s stunning façade and climb the Torre del Mangia for panoramic views. The guide’s commentary turned a simple visit into a richer experience, highlighting Siena’s medieval rivalries and history.

Next, you’ll explore San Gimignano, often called the “Manhattan of the Middle Ages” because of its skyline of medieval towers. The town’s narrow streets, squares, and the Duomo make for a captivating stroll. Most notably, you’ll taste Vernaccia wine and sample the famous gelato from Gelateria Dondoli, which has a reputation for winning awards. One guest said, “The gelato was a highlight—truly world-champion quality!”

The final stop is Casa Emma, a renowned estate where you’ll sample Chianti and Supertuscan wines, along with olive oil and vinegar. The guide’s focus on Sangiovese grapes and Tuscan culinary traditions adds educational value to the tasting. The visit’s relaxed pace and the opportunity to ask questions make it a favorite among guests.

Finally, a quick walk through Castellina in Chianti along Via delle Volte, an ancient street with medieval walls and a fortress, rounds out the day. It’s a peaceful way to absorb the authentic charm of the Chianti region.

Practical Details and What You’ll Love

Transportation is seamless, with air-conditioned vehicles ensuring comfort during long drives between towns. The group is small, which means more personalized service and the chance to ask questions freely—something visitors consistently praise.

Wine tastings are carefully curated, with two included during the trip. You’ll get to taste red and white wines from different estates, with guides explaining the nuances of Sangiovese, Vernaccia, and other varietals. Considering the prices of wine in Tuscany, the tastings offer excellent value, especially since some include educational insights into production.

Accommodations are at a charming agriturismo, giving you a taste of local rural life without sacrificing comfort. Breakfast is included, and you’ll have free time to relax or explore the property.

Timing is well-planned, with enough time at each stop to soak in the sights and enjoy tastings, but not so much that the days feel rushed. Some reviews mention that the schedule is fast-paced but manageable with a good guide who keeps things moving.

Who Would Enjoy This Tour?

This experience is best suited for those who want to combine culture, history, and wine without the stress of organizing logistics themselves. It’s perfect for travelers eager to explore multiple towns in a short period, with a focus on authentic wine tasting and scenic views.

Wine enthusiasts will appreciate the inclusion of top estates and expert explanations about production. Culture lovers will enjoy the visits to Siena, San Gimignano, and other hill towns, each offering their unique charm. Those who prefer a relaxed pace but still want a rundown of Tuscany’s highlights will find this tour ideal.

Final Thoughts

This two-day Tuscany tour offers a carefully balanced mix of historic towns, scenic landscapes, and world-class wines. The private transport and small group format mean you’ll enjoy a more personalized, relaxed experience than the typical bus tour. The knowledgeable guides, especially Mario, make all the difference—sharing stories, answering questions, and enhancing every stop with local insights.

While the schedule is packed, the overarching sense of discovery and the chance to taste some of Italy’s most celebrated wines make it a worthwhile adventure. Whether you’re a first-time visitor or returning to Tuscany, this tour provides a comprehensive and authentic glimpse into Italy’s most beautiful, wine-rich region.

If you’re seeking a well-organized, immersive experience with expert-guided wine tastings and historic sights, this tour will give you a memorable taste of Tuscany’s heart and soul.

FAQ

What is included in this tour?
The tour includes private transportation, all fees and taxes, two wine tastings, overnight stay in an agriturismo, breakfast, and tickets to key sites like Siena’s Duomo.

How much does the tour cost?
It costs approximately $1,070.58 per person, which covers the guided experience, tastings, and accommodations, making it quite a good value considering the number of tastings and visits.

Is this tour suitable for everyone?
Most travelers can participate, but those with mobility issues should consider the amount of walking and stairs involved in some towns. The tour is designed for those who enjoy wine, history, and scenic drives.

How far in advance should I book?
On average, it’s booked about 41 days before, indicating that spots fill up quickly—especially during peak seasons. Early booking helps secure your place.

Does the tour operate in all weather conditions?
Yes, but if canceled due to poor weather, you’ll be offered a different date or a full refund. Always check the weather forecast before setting out.

Are meals included?
No, lunch is not included, so plan to bring some snacks or arrange your own meals during free time.

How long is each day’s schedule?
Day 1 runs from morning to late afternoon, with stops at Montepulciano, Pienza, and Montalcino. Day 2 begins early and ends in the late afternoon after Siena, San Gimignano, and Chianti.

What makes this tour stand out?
The combination of personalized guidance, top-quality wine tastings, and visits to iconic towns makes it a highly memorable way to experience Tuscany’s wine culture and landscape in just two days.

This tour is a fantastic choice for travelers eager to enjoy Tuscany’s best-known towns and wines with expert guidance and a comfortable pace. Whether you’re celebrating a special occasion or simply want a deep dive into Tuscany’s rich wine heritage, it offers an engaging, well-rounded experience.