Private tour from Florence to CORTONA & MONTEPULCIANO

Discover the Beauty of Tuscany on a Private Day Trip from Florence

This private tour from Florence offers an easy way to explore two of Tuscany’s most captivating hill towns, Cortona and Montepulciano. Priced at $426.39 per person, it spans approximately 10 hours, providing a relaxed and personalized experience. The tour includes hotel pickup and drop-off, a luxurious Mercedes-Benz vehicle, and a private guide who tailors the itinerary to your interests. With rave reviews and a rating of 5.0 from 11 reviews, this excursion is highly recommended for lovers of scenic landscapes, historic towns, and authentic Tuscan charm.

While the tour does not include lunch, a delicious light meal at a family winery is part of the experience, along with the opportunity for a top-rated winery visit (additional expense). The flexibility and personalized attention make this tour a standout choice, especially for those who prefer comfort and insider tips over crowded group excursions.

Key Points

• Private, customized day trip from Florence to Cortona and Montepulciano
• Includes hotel pickup and drop-off in a luxury Mercedes-Benz with WiFi
• Visit Cortona, famous from Under the Tuscan Sun, for spectacular views and historic sights
• Explore Montepulciano, a charming medieval town known for Renaissance architecture and Vino Nobile vineyards
• Optional top-rated winery visit available (extra cost)
• Ideal for those seeking a relaxed, tailored experience with flexible stops and commentary

Starting Point and Transportation in Comfort

The tour begins at your hotel in Florence, where an English-speaking driver in a Mercedes-Benz V Class greets you. The vehicle offers air conditioning and WiFi, ensuring a comfortable start to your day. The private nature of the tour guarantees exclusivity, and the driver doubles as your guide, sharing insights throughout the journey. The pickup time is scheduled for 8:30 am, and the entire trip spans around 10 hours, making it suitable for a full day of exploration without feeling rushed.

Exploring Cortona’s Etruscan Roots and Panoramic Views

The first stop is Duomo di Cortona, a stone-walled town perched atop a hill about 600 meters above sea level. Enclosed by ancient Etruscan and Roman walls, Cortona offers stunning panoramic views of the surrounding valley and Lake Trasimeno. The town’s medieval streets and historic buildings are easily explored in about 1 hour and 30 minutes. Visitors appreciate the visual grandeur and the opportunity to walk through narrow alleys that evoke centuries past.

The town gained popularity from the book and film Under the Tuscan Sun, which helped boost its charm but does not overshadow its authentic appeal. The impressive architecture and scenic vistas are key highlights, making it a perfect first stop for those wanting to see Tuscany’s classic landscape.

A Relaxed Lunch at a Family-Owned Winery

After exploring Cortona, the tour proceeds to a family winery for a light lunch around 11:30 am. This meal provides a taste of Tuscan hospitality and cuisine, with local flavors served in a relaxed setting. The drive to Montepulciano follows, taking approximately 30 minutes through hilly landscape that showcases Tuscany’s breathtaking countryside.

This part of the day is flexible, as the driver can make photo stops along the way if requested. The lunch experience adds a personal touch to the day, allowing guests to enjoy regional food and wine without the rush of a large tour group.

Strolling Through Montepulciano’s Renaissance Streets

Arriving in Montepulciano around 2 pm, visitors find a medieval town of rare beauty. The main square, Piazza Grande, is surrounded by Renaissance palaces, historic churches, and charming alleys that invite exploration. The town’s elegant architecture and hidden corners are major draws, especially after its appearance in the Twilight film saga, which has increased its popularity.

A walk in Montepulciano offers plenty of photo opportunities, especially of the rolling vineyards that produce the famous Vino Nobile di Montepulciano. The town’s artistic and architectural heritage makes it a favorite for visitors seeking a quintessential Tuscan experience in just a couple of hours.

Optional Winery Visit to Sample Top-Rated Wines

For wine enthusiasts, the tour can include a visit to a top-rated vineyard (additional expense). This allows guests to sample local wines directly from producers and learn about Tuscan winemaking traditions. The visit complements the scenic beauty and historic charm with a taste of regional excellence, making for a memorable experience.

The Guide’s Flexibility and Personal Touch

One of the tour’s most praised features is the driver-guide’s ability to customize the day’s stops according to your interests. The guide is attentive, providing insights on local history, culture, and sights. During the drive, they can stop at scenic viewpoints or hidden spots to enhance the experience. The small group or private setting ensures personalized attention and flexibility, making this tour suitable for those who want a tailored, intimate day.

Practical Details and Ease of Booking

The tour is available with free cancellation up to 24 hours before the scheduled start, offering peace of mind. It is designed for most travelers, with casual dress and comfortable shoes recommended. The meeting point is conveniently located near public transportation, and the door-to-door service adds convenience for visitors staying in Florence.

Exceptional Reviews Highlight Guide Excellence and Stunning Sights

With a perfect rating of 5.0, reviews consistently praise the knowledgeable guides like Massimo, Luca, and Alessandro. Comments highlight their friendliness, flexibility, and ability to enrich the day with local stories. Travelers frequently mention spectacular views, beautiful towns, and delicious wine tasting experiences as key highlights.

Who Would Enjoy This Tour Most?

This private tour appeals most to those seeking comfort and customization, including couples, small groups, or solo travelers who prefer a personalized experience over crowded bus trips. It suits history and wine lovers and anyone wanting to see Tuscany’s iconic towns without the hassle of public transportation. The scenic drives and flexible stops make it ideal for photography enthusiasts and curious explorers alike.

Final Thoughts on the Tuscany Private Day Trip

This tour provides a well-balanced mix of scenic drives, historic sights, and local flavor, all within a relaxed, private setting. The luxury vehicle and personal guide ensure a comfortable and enriching day. While lunch is not included in the base price, the light meal and optional winery visit add significant value.

The high praise from reviews reflects consistent satisfaction with guides’ knowledge, views, and overall experience. This tour is perfect for those who want an authentic, tailored glimpse of Tuscany’s hill towns, especially if they appreciate comfort, flexibility, and local insights.

Frequently Asked Questions

Is the tour suitable for all fitness levels?
Yes, the tour involves walking through towns with cobblestone streets, but the pace is relaxed and flexible, so most fitness levels can comfortably participate.

Can I add a winery visit to the tour?
Yes, it is possible to include a visit to a top-rated winery for an additional cost. Be sure to advise when booking.

What should I wear?
Casual clothing and comfortable shoes are recommended, as walking through historic towns can involve uneven surfaces.

How far in advance should I book?
On average, this tour is booked 74 days ahead, so early reservation is advised to secure your preferred date.

What is included in the price?
The price covers hotel pickup and drop-off, driver/guide, transportation in a luxury Mercedes-Benz with WiFi, and all taxes, tolls, and parking fees. Lunch and winery visits are not included unless specified.

This private tour from Florence to Cortona and Montepulciano delivers a personalized, scenic, and culturally rich experience that captures the essence of Tuscany’s beautiful hill towns. It’s an excellent choice for those who wish to avoid the crowds and explore at their own pace with expert guidance.