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

An Authentic Journey Through Tuscany’s Art, Wine, and Landscapes

This private art and wine tour in Cortona and Montepulciano offers a full-day experience designed for those eager to explore Tuscany beyond the usual tourist spots. Priced at $279.26 per person, it includes round-trip transportation from Florence, visits to two charming towns, two wine tastings, and a delicious Tuscan lunch. With a rating of 5.0 from a recent review, this tour caters especially well to food lovers and culture enthusiasts who want an immersive experience in the Tuscan countryside.

The tour lasts approximately 8 hours, starting at 8:00 am, and includes personalized private transportation with a local driver. It’s perfect for those seeking a hassle-free day with a focus on authentic regional flavors, stunning views, and historical sights. Keep in mind that most travelers book this tour around 120 days in advance, making it a popular choice to plan ahead.

Key Points

• Private full-day experience exploring Cortona and Montepulciano
• Includes two wine tastings at renowned wineries
• Traditional Tuscan lunch with homemade pasta and regional cheeses
• Hassle-free pickup from Florence hotel or preferred location
• Stops at scenic viewpoints featured in “Under the Tuscan Sun”
• Educational visits to historic cellars and landmarks

Starting with the Enchanting Town of Cortona

The tour begins with pickup from your Florence hotel or preferred location, where a skilled driver transports you through the rolling Tuscan hills. The first stop is Cortona, a fortified Etruscan city perched about 600 meters above sea level. Here, you are given about 1 hour and 30 minutes for a self-guided exploration.

In Cortona, you’ll find the Piazza della Repubblica, the vibrant medieval streets, and Piazza Signorelli, all brimming with local shops and cafes. The Monastery of St. Francis is also on the itinerary, offering a peaceful retreat and a chance to admire historical architecture. The city’s vantage points provide breathtaking views of Lake Trasimeno and the surrounding landscape, making it a perfect spot for photos and leisurely strolls.

Scenic Drive and the “Under the Tuscan Sun” Photo Stop

After exploring Cortona, the group stops for a photo opportunity along the scenic route made famous by the film “Under the Tuscan Sun.” This brief stop offers a perfect framing for capturing the picturesque countryside, setting the tone for the subsequent visit to Montepulciano.

Discovering Montepulciano’s Underground Wonders

Next, the tour heads to Montepulciano, a hilltop town renowned for its Vino Nobile di Montepulciano DOCG. The visit includes the main square, Piazza Grande, the Government Palace, and two historic wine cellars. Inside these cellars, immense oak barrels hold the region’s celebrated wines, offering a glimpse into Tuscan winemaking traditions that date back centuries.

Visitors are free to explore the city’s charming alleys and appreciate the panoramic views of the Valdichiana valley from Montepulciano’s heights. The underground cellars with their impressive rock carvings and aging rooms add a unique touch to this wine-focused stop.

Wine Tasting at Cantina Fattoria della Talosa

In the heart of Montepulciano, the group visits Cantina Fattoria della Talosa for a guided tour of their historic cellar. As part of the experience, you’ll sample several wines, including Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, and the Riserva version, along with a Super Tuscan option, Filai Lunghi DOCG or Pietrose IGT.

The lunch is served at the winery, featuring homemade pasta—either Pici, Lasagne, or Cannelloni—along with Pecorino di Pienza, typical Tuscan cured meats, and fresh bruschettas. The Talosa Winery’s tunnels, carved into ancient rock, create a captivating setting where the wine ages gracefully, adding to the authenticity of the Tuscan experience.

Second Wine Tasting at Azienda Agricola Ercolani

Following lunch, the tour continues with a visit to Azienda Agricola Ercolani, a historic Renaissance cellar. The Ercolani family has played a pivotal role in establishing Vino Nobile di Montepulciano since the 1700s. Here, a guided cellar tour introduces the 7 to 8 wines in the family’s collection, carefully paired with appetizers.

This second tasting provides an opportunity to appreciate the variety and depth of the region’s wines, all in a setting rich with historical significance. The experience concludes with the group returning to Florence, or your chosen location, after approximately one hour.

Logistics and What’s Included

This private tour is designed for comfort and convenience, featuring air-conditioned transportation and a local driver. The tour includes two wine tastings at distinct wineries, a Tuscan lunch with homemade pasta, Pecorino, cured meats, and two bottles of regional wine. Bottled water and private transport round out the essentials.

The experience is flexible in terms of pickup points, with pickup offered from hotels, B&Bs, or private apartments in Florence. The tour operates most days, with confirmation received at booking and free cancellation available up to 24 hours before.

Who Will Love This Tour

This art and wine tour appeals most to food and wine enthusiasts, those interested in Tuscan landscapes, and visitors eager to explore less touristy towns like Cortona. The scenic drives, stunning views, and historic cellars make it a well-rounded day, combining culture, nature, and gastronomy.

While the tour is suitable for most travelers, those with mobility issues might want to consider the walking involved in towns and the uneven terrain within wine cellars. The 8-hour duration makes it ideal for those comfortable with a full-day trip.

Why This Tour Stands Out in Tuscany

What sets this tour apart is its focus on authentic regional experiences—a private, tailored approach that offers personalized attention. The combination of artistic exploration in Cortona, scenic views, historic wine cellars, and a delicious Tuscan lunch creates a well-balanced itinerary for a single day.

Plus, the two wine tastings at renowned wineries offer a comprehensive tasting experience. The guided tours inside the cellars deepen the appreciation for the region’s wine-making heritage. The scenic routes through famous landscapes and the opportunity to visit locations from a popular movie make this an engaging choice.

Final Thoughts on the Private Art & Wine Tour

This full-day experience delivers value with private transportation, local expertise, and a rich itinerary. It’s especially suited for those wanting a relaxed, immersive day in Tuscany, combining culture, scenery, and exceptional wines. The included lunch and wine tastings enhance the experience without hidden costs, making it a straightforward, enjoyable way to see two iconic towns.

The main limitations are the timed stops, which may feel rushed for some, and the walking involved in town explorations and cellar visits. Still, the personalized nature of the tour and the quality of the experiences make it a worthwhile choice for first-time visitors or those looking to maximize their day in Tuscany.

Frequently Asked Questions

Is transportation included in this tour?
Yes, private air-conditioned transportation from your Florence hotel or preferred location is included.

How long does the tour last?
The entire experience lasts approximately 8 hours, starting at 8:00 am.

Are wine tastings included?
Yes, you visit two wineries for tastings of Rosso di Montepulciano, Nobile di Montepulciano DOCG, and more.

Is lunch included?
Yes, a Tuscan lunch with homemade pasta, Pecorino cheese, cured meats, and regional wines is part of the tour.

Can I cancel this tour?
Yes, free cancellation is available up to 24 hours in advance for a full refund.

What are the main stops?
Stops include Cortona, scenic photo stop, Montepulciano (main square and underground cellars), Cantina Fattoria della Talosa, and Azienda Agricola Ercolani.

Is this tour suitable for children or those with mobility issues?
Most travelers can participate, but note the walking in towns and cellar visits, which may involve uneven terrain.

How far in advance should I book?
Most bookings are made about 120 days ahead, reflecting its popularity.

What makes this tour different from others in Tuscany?
Its private format, focus on authentic wineries, and visits to less touristy towns like Cortona make it a distinctive choice for an authentic Tuscan experience.