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

Discover the Charm of Tuscany on a Private Art & Wine Tour

If you’re dreaming of experiencing Tuscany beyond the usual crowds, this private art and wine tour in Cortona and Montepulciano might be just what you need. While we haven’t taken it ourselves, the glowing reviews and detailed itinerary suggest it’s a well-rounded way to see some of the region’s most iconic sights, taste local wines, and enjoy a delicious Tuscan lunch.

What stands out are two main things: first, the opportunity to explore two beautiful towns in one day, making the most of your time in Florence; second, the inclusion of two wine tastings paired with a hearty, authentic lunch. These elements make it especially appealing for those who want a relaxed yet comprehensive taste of Tuscany’s culture and flavors.

One thing to keep in mind is that the tour operates for about 8 hours, which means you’ll be on the move most of the day. If you’re someone who prefers a very leisurely pace or has mobility concerns, you’ll want to consider that.

This trip appears tailored for food lovers, wine enthusiasts, and anyone eager to see some of Tuscany’s most scenic spots without the hassle of planning or navigating on your own. It’s ideal if you’re looking for a structured day that combines sightseeing, tasting, and a touch of local history.

Key Points

• All-in-One Experience: Combines visits to Cortona and Montepulciano with wine tastings and a Tuscan lunch.
• Private Transportation: Hassle-free round-trip transfer from Florence in a comfortable, air-conditioned vehicle.
• Cultural Highlights: Explore historic streets, piazzas, and landmarks like the Monastery of St. Francis and underground cellars.
• Wine Tasting & Lunch: Sample a variety of local wines paired with homemade pasta, pecorino, and cured meats.
• Flexible & Personalized: Only your group participates, with options for group discounts and custom arrangements on request.
• Ideal for Food & Wine Lovers: Perfect for those wanting an authentic taste of Tuscany without the crowds.

An In-Depth Look at the Tour Itinerary

Starting Point: Pickup & Journey Through Tuscany

The tour kicks off at 8:00 am with pickup from your Florence hotel or chosen location. Having a private driver means you avoid the hassle of figuring out transportation, and you can sit back and enjoy the scenic drive through the rolling Tuscan countryside. The comfort of an air-conditioned vehicle helps keep everyone comfortable, especially if you’re traveling during warmer months.

First Stop: Cortona

Your first destination is the charming Etruscan city of Cortona. You’ll have approximately 90 minutes to explore on your own. The town is famous for its sweeping views over Lake Trasimeno and its role as the inspiration for Under the Tuscan Sun. Expect to stroll along medieval streets, admire the Piazza della Repubblica, and see sights like Piazza Signorelli.

The highlight here is the Monastery of St. Francis, a peaceful spot just outside the city center, perfect for a quick visit or some quiet reflection. The self-guided nature of this stop means you can take your time wandering, snapping photos, or grabbing a coffee.

Scenic Drive & Photo Stop

After Cortona, the group makes a brief photo stop along the route that features the landscape made famous in the film Under the Tuscan Sun. This offers a chance to capture Tuscany’s iconic rolling hills and vineyard-covered slopes, ideal for snapping memorable photos or just soaking in the views.

Next: Montepulciano & Underground Wonders

Your next stop is Montepulciano, a hilltop town renowned for its Vino Nobile di Montepulciano. Here, you’ll visit the main square, Piazza Grande, with its medieval architecture, and explore the historic cellars that house the region’s celebrated wines.

Two underground cellars await, where huge oak barrels rest, aging the wines and revealing the region’s long-standing wine-making tradition. This part of the tour is especially appreciated by wine lovers, as it offers an intimate look into the aging process and the region’s viticultural history.

Lunch & Wine Tasting at Cantina Fattoria della Talosa

After discovering Montepulciano’s streets and cellars, you’ll head to Cantina Fattoria della Talosa for a hearty Tuscan lunch. The meal features homemade pasta (like Pici, Lasagne, or Cannelloni), rustic pecorino cheese from Pienza, and a selection of cured meats such as ham, loin, and salami.

The winery itself is a sight to behold—spectacular tunnels carved into ancient rock lead to expansive rooms where the Nobile di Montepulciano ages gracefully. During your visit, you’ll enjoy a guided tour of the historic cellar and sample several wines, including Rosso di Montepulciano DOC, Nobile di Montepulciano DOCG, and a Super Tuscan like Pietrose.

Final Wine Tasting at Azienda Agricola Ercolani

The tour wraps up with a visit to Azienda Agricola Ercolani, a Renaissance-era cellar with deep roots in the region’s winemaking history. Here, a guided tasting of 7 or 8 wines, paired with appetizers, offers a fitting end to your day of indulgence.

This winery has roots dating back to the 1700s and played a pivotal role in the region’s wine history. The tasting experience, combined with the setting of ancient rock tunnels, leaves a lasting impression for those who appreciate authentic, historic winemaking environments.

Return Journey

Once your last tasting concludes, your driver will take you back to Florence, bringing an end to a full day of sightseeing, wine, and fantastic food.

The Value of This Tour

At $279.26 per person, this tour packs a lot of value. It includes private transportation, two wine tastings, a full Tuscan lunch, and visits to two of the region’s most picturesque towns. Given that the tour is private, you’re not stuck with strangers, allowing for a more relaxed experience where you can ask questions and customize your day slightly if needed (with advance request).

The inclusion of local expert guides at the wineries adds depth to the experience, helping you understand the wine-making process and regional history. Plus, the scenic drives and stunning views are an integral part of what makes Tuscany so special.

From the reviews, people seem to really appreciate the smooth organization—one reviewer called it “a wonderful way to see a little of Tuscany,” highlighting the prompt pickup and the ability to enjoy the full time allotted. Your fellow travelers also enjoyed the personable driver and the way the day was tailored to their interests, which suggests you’ll likely find this to be a seamless, enjoyable experience.

Who Will Love This Tour?

This experience is best suited for food and wine enthusiasts who want a comprehensive yet manageable taste of Tuscany. It’s ideal if you’re keen on exploring historical towns without the hassle of planning. Because it’s a private tour, it offers a more intimate experience, which is perfect if you prefer to avoid large groups.

Travelers seeking a balance of sightseeing, tasting, and culture will find this tour hits the mark. It’s also a good option for those wanting to maximize their day in Tuscany, as it combines multiple highlights into one well-organized trip.

However, if you’re looking for a very leisurely or flexible day, or if you’re not comfortable with structured tours, this might feel a bit packed. The timing is fixed, and a good portion of the day is on the move.

FAQs

How long is the tour?
The entire experience lasts about 8 hours, starting at 8:00 am with pickup and ending with drop-off back in Florence.

Is transportation included?
Yes, you’ll be transported in a private, air-conditioned vehicle, making the trip comfortable and stress-free.

Are wine tastings included?
Absolutely. You get two wine tastings at different wineries, including some of the best wines of the region like Nobile di Montepulciano and Super Tuscan.

What type of food is served for lunch?
The lunch features homemade pasta (like Pici, Lasagne, or Cannelloni), Pecorino cheese from Pienza, cured meats, and a selection of local wines.

Can I customize the experience?
The tour is private, so you can request some adjustments, but these should be made at least a week in advance.

Is the tour suitable for children or families?
While not specifically aimed at kids, the tour is generally family-friendly if children are comfortable with walking and wine tasting. Keep in mind, the focus is on wine and cultural sites.

What should I wear?
Comfortable shoes are recommended for strolling around towns and wineries. Dress according to the weather, especially if visiting in summer.

What’s the cancellation policy?
You can cancel for free up to 24 hours before the tour, allowing some flexibility if your plans change.

Final thoughts

If you’re after a well-organized, immersive day in Tuscany that combines artistic exploration, scenic views, and wine tasting, this private tour from Florence offers a compelling package. It strikes a good balance between sightseeing and indulgence, making it a great choice for those who want to see iconic towns without the stress of navigating on their own.

While it might feel a bit packed for a very relaxed day, the inclusion of a traditional Tuscan lunch and two wine tastings adds genuine value, especially if savoring regional flavors is your priority. Plus, traveling privately means you can enjoy the experience at your own pace, ask questions, and truly soak in the atmosphere.

For anyone eager to sample Tuscany’s best sights, wines, and cuisine in one seamless day, this tour could be just the ticket.

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