Private tour from Florence to CORTONA & MONTEPULCIANO

Traveling through Italy’s scenic countryside often feels like stepping into a storybook, especially when visiting the charming hill towns of Tuscany. If you’re looking to experience the beauty, history, and flavors of this region without the stress of public transport or rigid group tours, a private day trip from Florence to Cortona and Montepulciano might be just what you need. While we haven’t done this exact tour ourselves, the reviews and detailed itinerary paint a vivid picture of what you can expect—an elegant blend of scenery, culture, and personal touches.

What we really appreciate about this experience are two main things: the flexibility offered by a private guide who tailors the day to your interests, and the chance to indulge in leisurely exploration of two of Tuscany’s most picturesque towns. Plus, the inclusion of a scenic drive through the Arno Valley makes it feel like a genuine escape from city life. One thing to keep in mind, however, is that this isn’t a guided walking tour of the towns; instead, you’ll have the driver/guide to help navigate and suggest stops, which might not suit those wanting a deep, guided historical tour in each location.

This tour is ideal for travelers who value comfort, personalized experiences, and stunning vistas. It’s also great if you’re a fan of wine and scenery—adding a winery visit is an optional extra that many travelers found to be a highlight. If you’re traveling with family or just prefer a relaxed, unhurried approach to sightseeing, this private trip offers the right balance of exploration and comfort.

Key Points

• Private, customizable experience means you get to shape your day with your guide’s suggestions.
• Comfortable transportation in a Mercedes-Benz V Class ensures a smooth ride through Tuscany’s rolling hills.
• Stunning views and photo opportunities are abundant, especially around Cortona and Montepulciano.
• Flexible itinerary with optional add-ons like a top-rated winery visit for wine lovers.
• Ideal for those seeking a leisurely, personalized trip rather than a crowded group tour.
• Cost reflects the private, tailored nature of the experience, offering good value if you prioritize comfort and customization.

The Itinerary in Detail: What You Can Expect

Starting in Florence and Heading to Cortona

You’ll be greeted by your driver—Massimo, or another equally knowledgeable guide—in a comfortable Mercedes-Benz for the roughly 1.5-hour journey to Cortona. The town is perched on a hill approximately 600 meters above sea level, offering spectacular panoramic views over the surrounding valley and Lake Trasimeno. This setting alone makes Cortona a visual treat, and it’s topped with a bit of cinematic fame thanks to the film Under the Tuscan Sun.

The Duomo di Cortona is your first stop, where you can wander around this ancient church and soak in the atmosphere of a town that’s been home to Etruscans and Romans. From the reviews, we gather that visitors love the way the driver/guide—like Massimo—fills the time with interesting facts and suggestions, letting you explore at your own pace. One guest shares, “Massimo is a wonderful driver and guide. He knew how to fill our time—giving us plenty of spare time to explore.”

Leisurely Exploration and Photo Stops

With about an hour and a half at Cortona, you’ll have time to stroll its streets, admire the views, and soak in the medieval charm. The town’s setting is perfect for photos, so don’t forget your camera. The town’s popularity was boosted by the book and film, which makes wandering around the streets feel like stepping into a storybook.

From Cortona to Montepulciano

After Cortona, your driver will take you on a scenic 30-minute drive across the Tuscan hills to Montepulciano, arriving around 2 pm. This medieval hill town exudes elegance, with Renaissance palaces, narrow alleys, and ancient churches all waiting to be explored. Montepulciano’s reputation as a wine town is well-earned; you’ll see vineyards stretching across the hills, many of which produce the famous Vino Nobile.

Light Lunch and Wine Tasting (Optional)

A leisurely light lunch at a family winery is included in the itinerary, giving you a taste of local flavors in a cozy setting. If you’re a wine enthusiast—or just curious—you can opt to visit a top-rated winery (additional expense), which is often highlighted as a memorable part of the day. One review notes, “Our driver took us to a winery for wine tasting,” which was a highlight for many travelers.

Strolling Through Montepulciano

Post-lunch, you’ll have about two hours to explore Montepulciano. The town’s charming squares, Renaissance architecture, and hidden corners make for a lovely afternoon wandering. Given the recent film Twilight, the town has gained additional visitors, but it remains a peaceful escape from busier tourist spots.

Final Touches and Return to Florence

Your driver will bring you back to Florence, with the journey wrapping up after roughly 10 hours in total. The transportation is private, comfortable, and equipped with WiFi, so you can relax, catch up on photos, or even plan your next stop.

What the Reviews Say

The glowing reviews speak volumes about the quality of the experience. Travelers consistently praise the driver/guide—like Massimo or Luca—for their professionalism, knowledge, and friendly attitude. One reviewer mentions, “Massimo knew how to fill our time—giving us plenty of spare time to explore,” highlighting the flexibility that makes this tour special.

Many appreciated the stunning scenery and photo opportunities, describing the views as “gorgeous” and “breathtaking.” The inclusion of a wine tasting at a local vineyard is frequently noted as a highlight, with guests enjoying the chance to sample regional wines in a relaxed setting.

The tour’s personalized approach is a big draw; instead of being herded around like on large group tours, travelers feel free to explore at their own pace. One guest called the day “perfect,” emphasizing how the guide’s knowledge and flexibility made all the difference.

Cons and Considerations

The main consideration is that this isn’t a guided tour of the towns in the traditional sense. Instead, it’s a private drive with suggestions, so if you’re looking for detailed historical or artistic commentary in each town, this might not fully satisfy those needs. Also, the price—around $426 per person—reflects the private, tailored service, which might seem high if you’re traveling solo or on a tight budget. However, many find the comfort and customization worth the expense.

Transportation and Practicalities

A significant advantage of this tour is the luxurious transportation—a Mercedes-Benz V Class with air conditioning and WiFi. It’s perfect for relaxing as you journey through the Tuscan landscape. The pick-up and drop-off at your Florence hotel adds convenience, removing the hassle of figuring out public transport.

Timing begins at 8:30 am, giving you a full day to indulge in Tuscany’s delights. The planned stops are flexible to some extent, based on your preferences, thanks to the private nature of the tour.

Who Will Enjoy This Tour?

This experience suits travelers who want to see Tuscany’s highlights in comfort and style without the crowds. It’s especially appealing if you love scenic drives, stunning vistas, and local food and wine. The flexibility of a private guide makes it ideal for those who prefer a personalized experience—whether that means spending extra time in a town or adding a winery visit.

It works well for couples, small groups, or friends traveling together. While it’s not specifically tailored for families or children, those with an interest in history, scenery, and wine will find plenty to love.

The Sum Up

If you’re after a relaxed, personalized way to explore Tuscany’s iconic hill towns, this private tour from Florence to Cortona and Montepulciano hits many right notes. The combination of scenic drives, charming towns, optional wine tasting, and a knowledgeable guide creates a memorable day without feeling rushed.

The flexibility and comfort of private transportation mean you can truly take your time soaking in the views and exploring at your own pace. While it’s priced higher than a typical group tour, many travelers find the added intimacy, convenience, and tailored experience well worth it.

This tour is best suited for those who value comfort and customization and want to experience Tuscany’s beauty with ease—without the hassles of public transport or large crowds. If you’re looking to combine stunning scenery, excellent wine, and authentic small-town charm in one day, this private trip offers a compelling way to do just that.

FAQ

Is hotel pickup included?
Yes, the tour includes pickup and drop-off at your Florence accommodation, making it very convenient.

Can I add a winery visit?
Absolutely. It’s an optional add-on at your expense, and many guests enjoy including a visit to a top-rated winery for tastings.

What is the transportation like?
You’ll be traveling in a comfortable Mercedes-Benz V Class with air conditioning and WiFi, ensuring a smooth and relaxing ride.

How long is the drive from Florence to Cortona?
The drive takes about 1.5 hours, offering scenic views along the way.

Is this tour suitable for children?
While not explicitly marketed for families, it’s generally accessible for most travelers comfortable with a full day of sightseeing.

How much time do I get in each town?
Expect around 1.5 hours in Cortona and about 2 hours in Montepulciano, which allows for a relaxed exploration.

What’s the price per person?
The tour costs approximately $426.39 per person, reflecting its private, tailored nature.

Is the tour flexible?
Yes, the driver/guide can adapt the itinerary based on your interests and preferences.

What are the reviews like?
All reviews are perfect 5-star ratings, highlighting the professionalism, friendliness, and knowledge of the guides, as well as the stunning scenery and excellent wine experiences.

Exploring Tuscany’s hill towns in style and comfort can turn a regular vacation into a truly memorable experience. Whether you’re a lover of scenic drives, delicious food, or charming towns, this private tour offers a well-rounded taste of the region’s best.