Private tour from Florence to CORTONA & MONTEPULCIANO

Exploring Tuscany in Style: Private Tour from Florence to Cortona & Montepulciano

This private day trip from Florence offers an excellent way to experience some of Tuscany’s most captivating hill towns without the hassle of trains or crowded group tours. It’s designed for those who want the convenience of comfortable transportation, a tailored itinerary, and the flexibility to explore at your own pace—all with the luxury of a private guide and driver.

What really caught our eye is how seamlessly the tour combines iconic sights like Cortona’s panoramic views and Montepulciano’s Renaissance architecture with optional stops at local wineries. The fact that it’s customizable means you can prioritize what interests you most—be it history, food, wine, or simply soaking in the breathtaking scenery.

A potential consideration? The tour is quite full, with around 10 hours packed with sightseeing and travel. If you prefer a more leisurely, less structured day, this might feel a bit rushed. But for travelers eager to see key highlights in one day, it’s a smart, hassle-free choice.

This tour suits travelers who appreciate comfort, want a personalized experience, and are keen to explore Tuscany’s authentic charm. If you’re traveling from Florence and don’t want to spend hours on public transport or join large groups, this private option offers excellent value and a chance to create memorable moments.

Key Points

• Private, customizable experience: Your guide can tailor the day based on your interests, making every moment count.
• Comfortable transportation: Travel in a luxury Mercedes-Benz V Class with WiFi, air conditioning, and ample space for a relaxed journey.
• Authentic Tuscan towns: Visit Cortona, famous from Under the Tuscan Sun, and Montepulciano, known for Renaissance architecture and Nobile wines.
• Flexible stops: The driver/guide is attentive, allowing spontaneous photo stops or additional visits, like a local winery.
• Great reviews for guides: Guests praise knowledgeable guides like Massimo, Alessandro, and Luca, who add humor and insight.
• Ideal for wine lovers: You can add a visit to a top-rated winery (at your expense) for tastings and insights into Tuscany’s famed vineyards.

A Deep Dive: The Experience and What You’ll Actually Do

Pick-up and Departure

Your day begins with a hotel pickup in Florence in a luxury Mercedes-Benz V Class. This is a highlight on its own—comfortable, spacious, and equipped with WiFi, so you can relax or catch up on travel planning during the drive. The early start time of 8:30am means you’ll beat the crowds, arriving at your first destination, Cortona, around 10am.

Exploring Cortona: A Hilltop Beauty

The first stop is the Duomo di Cortona, a stunning church perched atop a hill about 600 meters above sea level. Enclosed by ancient stone walls dating back to Etruscan and Roman times, Cortona offers sweeping views over the surrounding valley and Lake Trasimeno.

Guests are often captivated by how picturesque and atmospheric the town is, especially from the vantage points along its narrow streets. One reviewer noted that Massimo, their guide, knew how to fill their time with just enough exploration, leaving plenty of room to soak in the scenery or take photos.

Since Cortona gained fame from Under the Tuscan Sun, many visitors love walking through the charming alleys and imagining their own romantic story. You might find yourself drawn to the local shops or stopping for a quick coffee at a piazza café, all while your guide offers insights into the town’s history and film connection.

The Drive to Montepulciano and Lunch

After an hour and a half exploring Cortona, your driver takes you on a gentle 30-minute drive across the rolling hills of Tuscany to Montepulciano. The landscape here, with its patchwork of vineyards and olive groves, is a postcard-perfect scene—ideal for photo enthusiasts.

Mid-morning, you’ll stop at a family-run winery for a light lunch and wine tasting. This experience is highly recommended by previous travelers, who describe the food as delicious and the wines as superb. Many reviewers specifically mention the quality of the wines and the friendly, knowledgeable staff. It’s an ideal way to taste some of Tuscany’s renowned Nobile wines and learn about the local winemaking traditions.

Exploring Montepulciano’s Medieval Charm

Arriving in Montepulciano around 2pm, you’re greeted by a town brimming with Renaissance architecture, charming squares, and hidden corners. The town’s Piazza Grande is its heart, a grand space lined with elegant palaces and impressive churches.

Guests have raved about how stunning Montepulciano is, noting its blend of history and beauty. One reviewer mentioned that the town’s atmosphere is perfectly suited for a leisurely stroll, stopping at cafes, browsing artisan shops, or simply soaking in the views of the countryside.

Since Montepulciano shot to fame as a filming location for the Twilight saga, it now often attracts vampire fans eager to see the “vampire town.”

Customization and Flexibility

One of the biggest perks is the tour’s flexibility. Guests frequently mention that the driver/guide, such as Massimo or Alessandro, are particularly skilled at customizing stops—for instance, if you want to spend more time at a winery, take photos, or explore additional sites.

The reviews underline that guides are not just informative but also charming, making the experience enjoyable and personal. You’ll find their knowledge covers history, local culture, and fun facts, making the towns come alive with context.

Return to Florence

Your day wraps up with a relaxed drive back to Florence, arriving around 6:30pm. Throughout the trip, you’ll enjoy WiFi and the comfort of your private vehicle—making this a stress-free way to see Tuscany’s highlights efficiently.

The Value of the Tour: How It Adds Up

At around $426 per person, this tour offers good value considering the personalized service, private transport, and the experiences included. The price covers hotel pickup and drop-off, a private guide/driver, luxury vehicle, and all taxes/tolls, making it a hassle-free, all-inclusive package.

While lunch is not included in the price, the stop at a highly-rated winery ensures you’ll enjoy quality local cuisine and wines without the need to hunt for restaurants on your own. Previous guests emphasize that the wine tasting and lunch are highlights, making it feel like an authentic, immersive experience rather than just sightseeing.

The fact that this tour is booked on average 74 days in advance indicates its popularity and value for travelers who want to secure a premium experience.

Who Will Love This Tour?

This private tour is ideal for those who value comfort and customization over large groups or overly structured schedules. It’s perfect if you’re eager to explore authentic Tuscan towns, taste local wines, and enjoy breathtaking scenery without the stress of navigation or public transport.

Travelers with a keen interest in history, architecture, and food will find this a fulfilling day. It’s especially suited for couples, small groups, or families seeking a personalized experience in Tuscany’s countryside.

The Sum Up

This private tour from Florence to Cortona and Montepulciano offers a harmonious blend of luxury, flexibility, and authentic cultural experiences. The guides’ local knowledge and friendly approach turn what could be just another sightseeing day into a memorable journey.

You’ll love the stunning views, charming towns, and the opportunity to sample delicious wines and local cuisine. The comfort of private transport and the ability to customize stops make it a top choice for travelers who want to maximize their time without feeling rushed.

While the tour is somewhat full-day, it’s an excellent way to tick off Tuscany’s most iconic hill towns efficiently and comfortably. If you’re after a personalized, high-quality experience that combines scenery, culture, and culinary delights, this tour will serve you well.

FAQ

Is hotel pickup included in the tour?
Yes, the tour includes pickup and drop-off at your Florence accommodation, making the day seamless and stress-free.

What is the transportation like?
Travel is in a modern Mercedes-Benz V Class, equipped with Air Conditioning and WiFi, providing plenty of space and comfort.

Can I customize the stops or experience?
Absolutely. The driver/guide is happy to adapt the schedule and stops based on your preferences.

Is lunch included?
No, lunch is not included in the price, but you can add a visit to a top-rated winery for tastings and light eating.

How long are the visits in each town?
Expect around 1 hour 30 minutes in Cortona and about 2 hours in Montepulciano, giving you enough time to explore without feeling rushed.

Is this a guided tour or just transportation?
It’s a private tour with a driver/guide who offers insights and recommendations, but the towns are explored at your own pace.

What should I wear?
Casual, comfortable shoes are recommended since you’ll be walking through cobblestone streets and historic sites.

Can I stop for photos during the drive?
Yes, your driver is happy to stop whenever you wish, making it easy to capture the stunning Tuscan landscape.

Is this tour suitable for all travelers?
Most travelers can participate; it’s designed to be accessible and enjoyable for anyone interested in Tuscany’s towns and scenery.

How far in advance should I book?
Most bookings are made about 74 days ahead, so it’s best to reserve early to secure your preferred date.

This private tour offers a fantastic way to experience Tuscany’s best-loved towns in a relaxed, personalized setting. Whether it’s your first visit or a return trip, it promises scenic views, charming towns, and memorable moments—perfect for those wanting a well-rounded, hassle-free day in Italy’s heartland.