Private Tour From Florence to Cortona and Montepulciano

Discover the Best of Tuscan Hill Towns on a Private Day Trip

This private tour from Florence offers an intimate journey into Tuscany’s historic towns of Cortona and Montepulciano. Spanning 9 hours, the experience combines scenic drives, cultural exploration, and wine tasting in some of Italy’s most picturesque landscapes. Led by an English-speaking driver, this tour is perfect for those seeking a personalized, relaxed way to enjoy Tuscany’s medieval charm.

The tour stands out with its focus on Cortona, famous for its role in Under the Tuscan Sun, and Montepulciano, renowned for producing the Vino Nobile wine. It also includes a lunch stop at a family winery, making it a well-rounded cultural and culinary experience. While the tour is highly praised for its guides’ knowledge and stunning views, it does require some walking on uneven surfaces, so comfortable shoes are recommended.

You can check availability for your dates here:

Key Points

• Private tour with flexible pickup from Florence in a Mercedes-Benz
• Duration: 9 hours, perfect for a leisurely exploration of Tuscan hill towns
• Visits include Cortona, famous for Under the Tuscan Sun, and Montepulciano, known for Vino Nobile
• Includes a light lunch at a family winery amid scenic vineyards
• Drivers are knowledgeable guides, providing context and tips
• Scenic drives with opportunities for photo stops at any preferred moment

Starting Point: Pickup and Comfortable Transportation

The journey begins with pickup at your hotel or nearby accommodation in Florence, using a luxurious Mercedes-Benz. This allows maximum comfort and convenience right from the start. The private group setting ensures an exclusive experience, free from the crowds typically found in larger tours.

This flexible pickup option is especially helpful for those staying in central Florence, and the vehicle is wheelchair accessible, accommodating guests with mobility needs. The driver also offers suggestions for the best way to enjoy each stop, making the experience tailored to your interests.

Exploring Cortona’s Etruscan and Roman Roots

Cortona is the first major stop, sitting atop a hill and surrounded by ancient stonewalls dating back to Etruscan and Roman times. From its dominant position, the town offers spectacular views over the valley and Lake Trasimeno. The town’s architecture features narrow cobbled streets, medieval buildings, and charming squares.

Visitors have ample free time to wander through Cortona’s streets, discovering hidden corners and local shops. The driver suggests the best spots to explore, making sure you see key sights and enjoy a relaxed atmosphere. This stop is ideal for those looking to soak in medieval charm and enjoy breathtaking vistas.

Tasting Tuscany’s Finest at a Family Winery Lunch

After exploring Cortona, the tour continues with a delicious light lunch at a family-run winery. The restaurant is set within the vineyard landscape, providing a rustic yet inviting atmosphere. The lunch typically features local specialties and regional wines, offering a taste of authentic Tuscan cuisine.

The winery stop also provides an opportunity to learn about wine production in the region, particularly the famous Vino Nobile. The driver can stop the vehicle at scenic spots if you wish to take photos during the journey, adding a personal touch to the day.

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The Scenic Drive to Montepulciano

Post-lunch, a relaxing 30-minute drive takes travelers across rolling Tuscan hills, with breathtaking landscape views. The road winds through vineyards and olive groves, offering ideal photo opportunities. The driver is attentive and flexible, ready to stop at any point for picture-taking or to simply enjoy the scenery.

This drive sets the tone for Montepulciano, emphasizing the beautiful countryside that characterizes this part of Tuscany. The journey itself is an experience, highlighting the region’s classic pastoral beauty.

Discovering Montepulciano’s Renaissance Elegance

Montepulciano greets visitors around 2:00 PM, revealing a medieval hill town with Renaissance palaces, ancient churches, and charming squares. Its elegant architecture and well-preserved historic center make walking through the town a delight.

The town has gained popularity after being featured in the Twilight film series, which has increased visitor interest. Walking through Montepulciano offers stunning views of the surrounding vineyards and landscapes, especially from Viale delle Libertà. The town’s wine shops within the walls provide the chance to sample and purchase the renowned Vino Nobile directly from local producers.

The Art of Wine Tasting and Local Delights

Many wine shops in Montepulciano offer tastings of the Vino Nobile, giving visitors the chance to appreciate the region’s famous red wine. This is an ideal way to deepen your understanding of Tuscan viticulture and enjoy authentic flavors.

The town’s charming streets and hidden corners invite exploration alongside wine tasting. The driver can suggest the best spots for both shopping and relaxing in the local ambiance, making sure you experience the culinary richness of Montepulciano.

The UNESCO Heritage of Val d’Orcia

The tour touches on the Val d’Orcia, designated by UNESCO as an exceptional example of how natural landscapes were redesigned during the Renaissance. The scenic views of rolling countryside, cypress trees, and medieval towns are part of this protected landscape.

Although the main stops are Cortona and Montepulciano, the driver highlights the importance of the Val d’Orcia’s landscape, adding to the sense of being immersed in a living picture of Tuscany’s natural beauty.

Practical Details and Tour Logistics

The entire 9-hour tour includes pickup and drop-off at your Florence accommodation, making logistics simple. The private group format allows for a flexible schedule, with the driver accommodating your interests and photo stops.

Comfortable shoes are recommended because of some walking on uneven surfaces during the stops in Cortona and Montepulciano. The tour also offers multilingual guides in Spanish, English, and Italian, with the driver providing in-depth commentary along the way.

Who Will Appreciate This Tour Most?

This private day trip is ideal for those who want a personalized, relaxed exploration of Tuscany’s iconic towns. It suits travelers who appreciate scenic drives, wine tasting, and medieval architecture. The flexible schedule and customizable stops make it a good choice for families, couples, or small groups of friends.

While it includes plenty of walking and photo opportunities, it is manageable even for those with moderate mobility, thanks to the wheelchair accessibility and driver’s assistance.

Final Thoughts on the Tuscany Private Tour

This 9-hour private tour from Florence offers a comprehensive glimpse of Tuscany’s hilltop towns with a focus on cultural, culinary, and scenic highlights. The guides’ expertise and scenic drives promise a relaxing yet enriching experience in some of Italy’s most celebrated landscapes.

Most visitors praise the warmth and professionalism of the guides, the stunning views, and the quality of the wine and food. The only potential consideration is the walking on uneven surfaces, but overall, the tour provides a balanced and delightful taste of Tuscan life.

Frequently Asked Questions

How do I book this tour?
You can reserve through the provided link, and the tour allows for free cancellation up to 24 hours in advance, giving flexibility to your plans.

What is included in the price?
The private transportation, guide services, and lunch at a family winery are included. Payment is pay later, so you can confirm your plans without immediate cost.

Is this tour suitable for children?
Yes, it is suitable for families, especially since the vehicle is wheelchair accessible and the pace can be adjusted.

Do I need to bring my own shoes?
Comfortable shoes are recommended due to walking on uneven surfaces in both Cortona and Montepulciano.

Can I customize the stops?
The tour is private, and the driver offers suggestions and can stop at any time you desire for photos or exploration.

How long is the drive between Cortona and Montepulciano?
The drive lasts approximately 30 minutes through scenic landscapes, with the option for stops along the way.

What kind of views will I see?
Expect spectacular views over valleys, vineyards, and cypress-lined roads—photographers will love the landscape.

Is there free time in Montepulciano?
Yes, after arriving around 2:00 PM, you have time to explore the town at your own pace, including wine tasting and browsing local shops.

What languages are guides available in?
Guides speak Spanish, English, and Italian, ensuring clear commentary and assistance throughout the day.

What is the main benefit of this private tour?
The personalized itinerary, flexible timing, and expert guides make it a comfortable way to experience Tuscany’s most charming towns without the crowds.

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