Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

A Full Day Exploring Tuscany’s Artistic and Culinary Heartland

This private art and wine tour takes you from Florence to two of Tuscany’s most iconic towns—Cortona and Montepulciano—all in about eight hours. For $279.26 per person, you’ll enjoy round-trip transportation, two exclusive wine tastings, and a traditional Tuscan lunch in a historic winery. With a maximum of just your group and a knowledgeable driver, this experience promises both comfort and personalized attention.

What we particularly love about this tour is the chance to see the landscape that inspired “Under the Tuscan Sun” and to sample some of Italy’s finest wines in their historic cellars. The combination of scenic views, cultural highlights, and authentic food makes this a well-rounded taste of Tuscany. However, keep in mind that it’s a full day—so, if you prefer leisurely pacing or more time in each spot, you might find the schedule a bit tight.

This tour suits travelers who want an efficient, curated experience—especially those with a passion for art, good wine, and genuine regional flavors. It’s ideal if you’re short on time but eager to make the most of a day in Tuscany, and it’s particularly beneficial for first-timers eager to see a couple of the most photogenic hill towns with minimal hassle.

Key Points

• All-in-One Experience: Combines visiting Cortona and Montepulciano with wine tastings and lunch.
• Convenience: Includes private transportation, hotel pickup, and round-trip transfer.
• Authentic Tastings: Enjoy two tastings at renowned wineries, including Nobile di Montepulciano and Super Tuscan wines.
• Cultural Highlights: Explore historic city centers, piazzas, and underground wine cellars.
• Scenic Views: Expect breathtaking vistas of the Tuscan countryside and Lake Trasimeno.
• Ideal for Food and Wine Lovers: The experience is tailored for those keen to venture off the typical tourist trail.

Detailed Review of the Tour Experience

Starting Point and Transportation

Your day begins with hotel pickup in Florence, which is a real advantage. This private tour means you won’t be stuck in a large bus or waiting for other travelers. The vehicle is air-conditioned, making the roughly two-hour drive through the rolling Tuscan hills comfortable and scenic. Your driver, though not a guide, provides commentary and adapts to your pace, a nice touch that keeps the mood relaxed.

Exploring Cortona: A Town of Art and Views

Arriving in Cortona, you get about an hour and a half to wander at your own pace. This Etruscan hill town is famous for its medieval streets, piazzas, and spectacular views. The Piazza della Repubblica and Piazza Signorelli are highlights, with charming shops and cafes lining the streets. You’ll appreciate the opportunity to take photos of Lake Trasimeno, visible from strategic viewpoints.

A visit to the Monastery of St. Francis adds a touch of serenity, and the entire walk through Cortona’s historic center feels like stepping into a classic Italian postcard. The free admission means you can focus your budget on the wine and lunch, and the town’s relaxed atmosphere makes it perfect for a brief, yet memorable visit.

Scenic Drive and Photo Stop

Following your time in Cortona, the group makes a photo stop along the scenic route featured in “Under the Tuscan Sun.” Here, you’ll get a glimpse of the landscape that has inspired countless artists and writers, offering some fantastic photo opportunities and a chance to stretch your legs.

Montepulciano: A Town of Wine and History

The next stop is Montepulciano, known worldwide for Vino Nobile di Montepulciano. Here, you’ll explore the main square, Piazza Grande, and see landmarks like the Government Palace. The underground “Wonders” tour takes you into cellars carved into ancient rock, giving a fascinating view into the region’s long-standing winemaking tradition.

Your guides focus on the region’s rich history of viticulture, with immense oak barrels aging the famous wines. As one reviewer notes, the “spectacular tunnels carved into ancient rock” are a highlight—and provide a tangible connection to the centuries-old craftsmanship.

Lunch and Wine Tasting at Cantina Fattoria della Talosa

In Montepulciano, the lunch at Fattoria della Talosa is a major highlight. The meal features homemade pasta—choices like Pici, Lasagne, or Cannelloni—paired with Pecorino di Pienza and a selection of Tuscan cured meats. This is not just a meal; it’s a chance to taste regional flavors crafted with pride.

The winery tour inside the historic cellar reveals spectacular tunnels and expansive aging rooms, adding a sense of history and craftsmanship. Tasting the Nobile di Montepulciano DOCG and Riserva wines, complemented by tasting Super Tuscan options, allows wine enthusiasts to appreciate the depth and breadth of regional winemaking.

Second Winery Visit: Azienda Agricola Ercolani

The second wine tasting takes place at Cantina Ercolani, a family-run hotel with a history dating back to the Renaissance. The guided tour of the cellar ends with a tasting of 7 to 8 wines, paired with small appetizers. This gives you a thorough sampling of the region’s best offerings and a deeper understanding of the history behind the wines.

Returning to Florence

After a full day of sightseeing, tasting, and exploring, your driver will take you back to your Florence hotel. The comfortable vehicle, combined with the well-planned schedule, means you’ll arrive in the evening satisfied but not exhausted—ready to recount your highlights or plan your next day.

Authentic Experience and Practical Details

This tour is designed to maximize your time—covering cultural highlights, scenic views, and authentic tastings—without rushing. The private nature ensures you can customize slightly or ask questions, which many travelers find makes the experience more engaging.

Cost-wise, at $279.26, it offers great value considering all inclusions: luxury transportation, lunch, and two wine tastings in renowned wineries. You’re paying for a curated experience that balances sightseeing with regional culinary delights and wine culture.

The small group size, or rather private setup, offers a more intimate experience than larger tours, allowing for a more relaxed exploration and personalized attention.

How the Experience Feels

Many travelers have shared positive impressions. One reviewer called it a “wonderful way to see a little of Tuscany,” appreciating the prompt pickup and adaptable pacing. The scenic views and the chance to explore hidden wine cellars stand out as unforgettable moments. The authenticity of the lunch and the quality of the wines are frequently praised.

Potential Drawbacks

The main consideration is the full-day schedule. If you prefer lingering longer in each town or dislike tight schedules, this might feel rushed. Also, without an included guide, you’ll rely on your driver for commentary, which varies in depth.

Who Is This Tour Best For?

If you crave a well-organized, culturally rich experience that combines art, history, and wine, this tour is a winner. It’s perfect for those who want to see iconic Tuscan towns without the hassle of driving or planning logistics. Food and wine lovers will appreciate the authentic tastings and regional cuisine, and anyone short on time but eager for a comprehensive taste of Tuscany will find this a rewarding choice.

Frequently Asked Questions

Is pickup included in the tour?
Yes, the tour includes hotel pickup from your Florence accommodation, making the start of your day seamless.

How long is the total tour?
The entire experience lasts approximately 8 hours, including travel, sightseeing, lunch, and tastings.

Are the wine tastings in different wineries?
Yes, you will visit two different wineries—the first at Cantina Fattoria della Talosa and the second at Azienda Agricola Ercolani.

Is lunch included?
Absolutely. The Tuscan lunch featuring homemade pasta, Pecorino, and cured meats is included in the price.

What can I expect at each stop?
In Cortona, you’ll explore the historic streets and enjoy panoramic views; in Montepulciano, you’ll tour underground cellars and sample renowned wines.

How much free time do I get in each town?
You’ll have about 1.5 hours in Cortona and 2 hours in Montepulciano, enough to walk around, take photos, and soak in the atmosphere.

Is this a group or private tour?
It’s a private experience, so only your group will participate, allowing for a more personalized adventure.

Can I request a guide?
Guided tours are available upon request, planned one week in advance, with an additional fee.

What’s the best season to take this tour?
While not explicitly stated, Tuscany’s most pleasant weather for this kind of trip is generally in spring or early fall.

To sum it up, this private art and wine tour strikes a fine balance between cultural discovery, scenic beauty, and gastronomic delights. It’s especially suited for travelers who want to experience Tuscany’s essence without the hassle of navigating on their own. With a focus on authentic experiences, delicious regional food, and outstanding wines, it’s a memorable way to deepen your appreciation for Italy’s most famous countryside. Whether you’re a first-time visitor or a seasoned traveler, this day trip offers a rich taste of Tuscany’s art, history, and flavors in one comprehensive package.