Private Tour From Florence to Cortona and Montepulciano

If you’re dreaming of soaking up the quintessential Tuscan landscape and history, a private tour from Florence to Cortona and Montepulciano might just be the perfect way to do it. While we haven’t personally taken this exact trip, the reviews and details paint a pretty appealing picture—especially if you’re after a blend of culture, stunning scenery, and some good wine.

What stands out for us? First, the ease of having an expert driver guide you through these picturesque towns, taking care of logistics so you can simply enjoy the experience. Second, the chance to taste some of the region’s renowned wines and sample delicious local foods. On the flip side, this tour involves some walking on uneven surfaces, so comfortable shoes are a must.

This experience seems ideal for travelers wanting a curated taste of Tuscany’s highlights without the hassle of planning every detail. It suits those who appreciate scenic drives, cultural insights, and a relaxed pace—probably not the best fit if you’re after a super active or tightly scheduled day, or traveling with very young children needing more entertainment.

Key Points

• Private, Comfort-Oriented Experience: Enjoy a tailored day with a dedicated driver, ensuring flexibility and personalized attention.
• Stunning Scenery & History: Walk through towns with roots in Etruscan and Roman times, plus breathtaking views of the Tuscan countryside.
• Cultural & Culinary Highlights: Visit Cortona, famed for “Under the Tuscan Sun,” and Montepulciano, renowned for its wine, with a delicious lunch at a family winery.
• Flexible & Relaxed Pacing: The itinerary allows for spontaneous photo stops and leisurely exploration.
• Expert Guides & Local Insights: The driver also acts as a guide, sharing stories, history, and recommendations.
• Good for Wine & Food Lovers & Scenic Seekers: The tour caters well to those who love tasting regional wines and enjoying impressive landscapes.

You can check availability for your dates here:

A Close Look at the Day’s Journey

The day begins with a comfortable pickup in Florence—your driver will meet you at your hotel in a sleek Mercedes-Benz, setting a tone of ease and luxury. From there, the drive into the heart of Tuscany is a scenic journey that immediately puts you in the mood for a relaxed, cultural adventure.

First Stop: Cortona

Arriving in Cortona, you’re greeted with views that feel straight out of a postcard. This hilltop town is surrounded by ancient stone walls dating back to Etruscan and Roman times, which immediately hints at its long history. The town’s elevated position offers sweeping vistas of the valley below, including Lake Trasimeno, making it perfect for photography or just soaking in the landscape.

What to do in Cortona? The options are plentiful, whether you want to wander through narrow cobbled streets, peek into quaint shops, or simply relax in a piazza. Many visitors find the town’s charm heightened by the literary fame it gained from Frances Mayes’ “Under the Tuscan Sun”—and the movie with Diane Lane. Some reviews mention that the town has become increasingly popular in recent years, which might mean more crowds than in the past—but that’s part of the lively charm.

Your driver/guide will suggest the best spots to explore or relax, so if you’re after a peaceful stroll or a scenic viewpoint, they’ll point you in the right direction. The approximately two-hour visit gives enough time to absorb the atmosphere without feeling rushed.

Lunch at a Family Winery

Post exploration, you’ll head to a family-owned winery for a light lunch around 11:30 AM. This isn’t just a quick bite; it’s an opportunity to indulge in authentic Tuscan flavors paired with local wines. The reviews praise this stop as “delicious,” and many mention the friendly, welcoming atmosphere of the winery. Tasting local wines and enjoying traditional Tuscan snacks makes for a true gastronomic experience, and it’s a nice break before heading to the next town.

Scenic Drive to Montepulciano

After lunch, the journey continues on a 30-minute drive into the rolling hills surrounding Montepulciano. As you inch closer, you’ll notice the landscape transform into iconic Tuscan scenery—vineyards, olive groves, and patchwork farmland.

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Montepulciano: A Medieval Treasure

Arriving in Montepulciano, you’ll see why it’s a favorite for many visitors. This medieval hill town is a feast for the eyes—with Renaissance palaces, ancient churches, charming squares, and secret corners waiting to be discovered. Its popularity has risen in recent years, partly thanks to the filming of the “Twilight” saga sequel “New Moon,” bringing extra attention and visitors.

A walk through Montepulciano’s streets reveals a blend of history, architecture, and sweeping views. You’ll want to take your time to admire the elegant facades and perhaps pop into some wine shops inside the city walls, where you can taste and purchase the famous Vino Nobile. The town’s elevated position offers stunning vistas over the countryside, making it perfect for photography or simply soaking up the atmosphere.

Winetasting & Exploring

Many reviews highlight the quality of the wine tastings in Montepulciano’s shops—some even describe it as “the best of Tuscany” in terms of wine. The town’s historic cellars and wine shops offer the chance to savor the legendary Nobile wine, often paired with local snacks.

Walking around, you’ll notice the timeless beauty of the town—spotting Renaissance palaces, visiting churches, and wandering through enchanting alleyways. It’s a rich visual and cultural experience, ideal for those who love history and architecture.

Tour Details & Practicalities

The entire trip lasts about nine hours, making it a full but relaxed day. The transport is an enclosed, private Mercedes-Benz, ensuring comfort, especially if the weather is warm or unpredictable. The tour is private, with the driver also acting as your guide, sharing insights in English, Spanish, or Italian.

You can reserve now and pay later, with full cancellation allowed up to 24 hours in advance—flexibility that’s often appreciated when planning trips. The tour caters to wheelchair users and is suitable for groups seeking a personalized experience.

What to Pack & Prepare

Bring comfortable shoes, as there will be walking on uneven surfaces. Sunscreen, a hat, and sunglasses are advisable if the weather is sunny. The scenic stops and photo opportunities are plentiful, so don’t forget your camera.

The Authenticity & Value of the Experience

Based on reviews, guests consistently praise the knowledgeable guides and drivers, with some describing their guides as courteous, friendly, and informative. The scenery is a highlight—standing on the hilltops and looking out over Tuscany’s famous landscape truly makes an impression.

The lunch at a family winery receives particular praise, with many reviewers calling it “delicious” and highlighting the chance to taste local wines and snacks. This kind of experience provides a genuine taste of regional culture, not just a quick tourist stop.

Guests also mention the comfort of the vehicle and the flexibility the private tour offers—drivers willing to stop for photos or adjust timing. One reviewer described the driver as “incredibly good,” emphasizing the importance of a friendly, attentive guide when exploring unfamiliar towns.

What Could Be Better?

While many reviews are glowing, some travelers noted minor inconveniences—like the app’s difficulty coordinating the pickup location or the fact that there’s some walking involved. If you’re not comfortable with uneven terrain, it’s worth considering this before booking.

Who Is This Tour Best For?

This tour is ideal for couples, small groups, and anyone who appreciates a personalized, relaxed day exploring Tuscany’s highlights. It’s perfect if you love wine, scenic drives, and discovering charming towns without the pressure of large groups or rigid schedules.

It suits those who want a mix of culture, history, and leisure—an experience that balances guided insights with free time for personal exploration. If you’re traveling with family or friends who enjoy scenic views and wine tastings, this could be a memorable way to spend a day.

FAQs

Is this tour suitable for people with mobility issues?
The tour involves walking on uneven surfaces, so comfortable shoes are recommended. If you have specific mobility concerns, it’s best to check with the provider for accommodations.

Can I customize the timing or stops?
Since it’s a private tour, the driver/guide can suggest the best options, and you may be able to personalize the schedule slightly. However, the core itinerary is fixed.

What should I bring?
Comfortable shoes, sun protection, and a camera are advisable. The tour involves outdoor exploration, so dress accordingly.

Are meals included?
The tour includes a light lunch at a family winery, where you can enjoy regional specialties and wine tastings.

How long is the drive between towns?
The drive from Cortona to Montepulciano takes around 30 minutes, with plenty of opportunities for photos along the way.

Is the tour suitable for children?
While not specifically designed for kids, families with older children who enjoy walking and wine tasting might find it enjoyable. Keep in mind the walking surfaces and the tasting aspect.

What languages are available for the guide?
The driver/guide speaks English, Spanish, and Italian, accommodating most travelers.

What is the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, offering flexibility should your plans change.

Final Thoughts

If you’re after a personalized day exploring Tuscany’s iconic towns, this private tour from Florence offers a well-balanced mix of stunning views, cultural richness, and culinary delights. The flexibility, combined with knowledgeable guides and comfortable transportation, makes it a compelling choice for travelers who want to soak up Tuscany’s essence without the hassle of self-driving or navigating public transport.

While it’s not the cheapest option out there, many guests find the value in the intimate, tailored experience—especially the chance to taste local wines, walk charming streets, and enjoy the breathtaking landscapes that define this part of Italy.

For those who crave a relaxed, scenic, and culturally engaging day, this tour seems to tick all the boxes. Just pack your walking shoes and prepare to fall in love with Tuscany’s timeless charm.

You can check availability for your dates here: