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

A detailed look at the Private Art & Wine Tour in Cortona and Montepulciano

If you’re dreaming of a day that combines Italy’s stunning countryside, charming towns, and world-renowned wines, this private tour from Florence might just be your perfect match. Designed for those who want to blend sightseeing with authentic wine experiences, it offers an all-in-one package: visits to Cortona and Montepulciano, two wine tastings, a delicious Tuscan lunch, and hassle-free transportation.

What we really love about this tour is how seamless and personalized it feels. From the moment you’re picked up at your hotel, the experience is tailored to offer a relaxed pace and plenty of authentic moments. However, it’s worth noting that the full-day format means a fair amount of travel, so it’s best suited for those comfortable with a busy schedule.

One thing to consider is the group size—while it’s a private tour, the itinerary is packed, which might mean a quick visit to each highlight. Still, for lovers of wine, scenic views, and Tuscan charm, this experience offers excellent value. If you’re looking for a way to see two iconic towns while sampling some of Italy’s best wines, this tour is a very appealing option.

Key Points

• Customized Private Experience: Perfect for those who want a tailored, intimate day out in Tuscany.
• All-Inclusive Value: Lunch and two wine tastings are included, making the day both indulgent and stress-free.
• Scenic & Cultural Stops: Explore Cortona’s medieval streets and Montepulciano’s underground cellars with ease.
• Hassle-Free Transportation: Round-trip private transfer from Florence eliminates the stress of driving or navigating public transport.
• Authentic Wine & Food: Sample local wines like Vino Nobile di Montepulciano alongside traditional Tuscan dishes.
• Ideal for Wine & Culture Enthusiasts: Perfect for travelers who want a deeper, more personal look at Tuscany’s culinary and viticultural heritage.

An In-Depth Review of the Cortona & Montepulciano Wine & Art Tour

Starting Point & Transportation

The tour kicks off early at 8:00 am, with a private, air-conditioned vehicle ready to whisk you away from your Florence accommodation. Having your own private driver—not just a guide—means you’re in control of your schedule, and the journey itself becomes part of the experience. The driver is described as personable and adaptable, making any last-minute requests or adjustments easier.

The transfer from Florence to Tuscany’s rolling hills sets the tone for the day—expect sweeping views that look like they stepped out of a painting. The drive to Cortona is about an hour and a half, giving you plenty of time to relax and take in the scenery.

Exploring Cortona: A Medieval Jewel

Our first stop is Cortona, a city that feels like walking through a living postcard. Perched roughly 600 meters above sea level, this ancient Etruscan town offers panoramic views of Lake Trasimeno and the surrounding countryside.

The one and a half hours allocated here is perfect for a leisurely self-guided stroll. We loved the way the tour allows you to soak in Cortona’s atmosphere—wandering through narrow medieval streets, browsing artisan shops, and taking photos of the stunning vistas from Piazza della Repubblica.

Highlights include the charming Piazza Signorelli, a hub of local life, and the Monastery of St. Francis, which provides a peaceful retreat from the bustling streets. Reviewers note that the city’s charm lies in its authenticity—no overly touristy vibe here, just real life in Tuscany. One reviewer shared, “Taking this tour was a stroke of genius! The views are breathtaking, and the town feels like stepping into a movie.”

Scenic Drive & Photo Stop at “Under the Tuscan Sun” Scene

After Cortona, the journey continues with a quick stop along the route made famous by the film “Under the Tuscan Sun”. This photo opportunity adds a touch of cinematic magic, making for some beautiful snaps that will remind you of the movie’s idyllic Tuscany setting.

Montepulciano: Underground & Historic Charm

Next, the tour takes you to Montepulciano, a hilltop town famous for its wine and medieval architecture. The two-hour exploration includes a visit to the Piazza Grande, the heart of the town, where you can admire the elegant Palazzo Comunale and the Cathedral of Sant’Albino.

One of the main attractions here is the underground cellars, where some of Italy’s most prized wines—Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC—age in enormous oak barrels. These cellars reveal the deep winemaking traditions of the region and provide a fascinating glimpse into Tuscany’s viticultural history.

Reviewers praise the tour’s focus on hidden wine cellars, saying it feels like discovering secret treasures. It’s a chance to learn about how tradition and craftsmanship have shaped the local wine scene. As one reviewer puts it, “The underground wine cellars are incredible, and I appreciated the chance to see and learn about the aging process up close.”

Tuscan Lunch at Cantina Fattoria della Talosa

One of the tour’s highlights is a delicious Tuscan lunch at Fattoria della Talosa, a historic winery in Montepulciano. The guided tour of the cellar reveals the ancient tunnels carved into rock, where the wine matures gracefully over time.

The meal is hearty and authentic—homemade pasta (your choice of Pici, Lasagne, or Cannelloni), accompanied by Pecorino di Pienza, cured meats, and bruschettas. Pair that with the winery’s finest wines, including Nobile di Montepulciano Riserva and Super Tuscan selections, for a true taste of local flavors.

Reviewers mention that the lunch is generous and thoughtfully curated, making it a satisfying and immersive experience. One says, “The food felt like a home-cooked meal, and the wine was outstanding. It was the perfect balance of indulgence and authenticity.”

Final Wine Tasting at Azienda Agricola Ercolani

The last stop features a visit to Cantina Ercolani, a family-owned estate dating back to the Renaissance. Here, you’re treated to a guided tour of the historic cellar and a tasting of 7-8 wines, paired with light appetizers.

This second tasting offers a deeper dive into the region’s winemaking heritage, especially focusing on Vino Nobile di Montepulciano’s roots. Reviewers note the expertise of the guides and the chance to sample a wide variety of wines—great for those wanting to expand their palate and knowledge.

Return to Florence

After the wine tasting, it’s a comfortable drive back to Florence, concluding around 5-6 pm. Many mention how smoothly the day flows, thanks partly to the private transportation and well-timed stops.

The Value of This Tour

At $279.26 per person, this experience packs a lot of value. You get transportation, a traditional Tuscan lunch, two wine tastings, and visits to two of the most picturesque towns in the region—all without any of the hassle of planning or driving. The tour’s private nature ensures a personalized touch, making it ideal for couples, friends, or small groups.

The fact that most travelers book this about 120 days in advance speaks to its popularity—an indicator that it delivers on what it promises. The flexibility and focus on authentic experiences make it stand out from generic group tours.

Who Should Consider This Tour?

This experience is tailor-made for food and wine lovers, as well as travelers keen on experiencing Tuscany beyond the usual tourist spots. It’s perfect if you want a more intimate, in-depth look at local culture with the convenience of door-to-door service.

However, if you prefer a slower pace or want more time in each location, keep in mind that this is a full-day tour with a tight schedule. It suits those who enjoy active sightseeing combined with culinary and wine indulgence.

The Sum Up

This private art and wine tour offers an excellent way to explore Tuscany’s highlights with comfort and authenticity. You’ll visit two picturesque towns—Cortona and Montepulciano—without the stress of driving or navigating public transport. The inclusion of local wine tastings, a hearty Tuscan lunch, and sightseeing makes this a well-rounded experience that appeals to lovers of food, wine, and cultural discovery.

For those wanting a personalized, immersive day in Tuscany—especially if wine tasting is high on your list—this tour provides a compelling mix of scenic beauty, delicious food, and historical charm. The private setting guarantees a relaxed pace, meaning you can truly savor the experience rather than rush through it.

In sum, this tour is best suited for travelers who value quality over quantity, seek authentic experiences, and want the convenience of door-to-door service. The combination of stunning vistas, delicious local flavors, and rich history makes it a memorable way to experience the Tuscan countryside.

FAQ

Is pickup included in this tour?
Yes, the tour offers pickup from your Florence hotel or preferred location, making it convenient and stress-free.

How long is the tour?
The entire experience lasts approximately 8 hours, starting at 8 am and concluding in the late afternoon or early evening.

Are the wine tastings included in the price?
Yes, you enjoy two wine tastings at different local wineries, featuring Rosso di Montepulciano, Nobile di Montepulciano, and Super Tuscan wines.

Is lunch included?
Absolutely. You’ll have a traditional Tuscan lunch with homemade pasta, Pecorino cheese, cured meats, and bruschettas, paired with wines.

Can I customize the experience?
This is a private tour, so you can discuss preferences with your driver or guide, though the itinerary is generally fixed.

What are the main highlights?
The highlights include exploring Cortona’s medieval streets, visiting Montepulciano’s underground cellars, tasting local wines, and enjoying a hearty Tuscan lunch.

Is this suitable for children?
While the tour is primarily designed for adults, children comfortable with a full day of sightseeing and food might enjoy it—though wine tastings are for guests of legal drinking age.

How far in advance should I book?
Most travelers book about 120 days ahead, ensuring availability for this popular, well-reviewed experience.

This in-depth review aims to help you decide whether this immersive day in Tuscany matches your travel dreams. Whether it’s the charm of Cortona, the wine cellars of Montepulciano, or the scenic landscapes you crave, this tour offers a well-rounded and authentic slice of Italy.