Exploring the enchanting towns of Cortona and Montepulciano is an opportunity to take in the rich history and captivating architecture of Tuscany. This private tour from Florence offers a luxurious and personalized experience, where visitors can stroll through cobblestone streets, savor authentic local cuisine, and discover the impressive sites that have made these destinations renowned. With the option to visit local wineries and sample the renowned Vino Nobile, this tour promises an unforgettable journey through the picturesque Arno Valley. Discover the charm and allure that await…
Good To Know
-
This private tour from Florence takes visitors to the historic towns of Cortona and Montepulciano, showcasing their Renaissance architecture and local wine heritage.
-
The tour includes hotel pickup and drop-off, a knowledgeable driver-guide, and transportation in a luxurious Mercedes-Benz V Class vehicle, ensuring a seamless experience.
-
Guests can explore the cobblestone streets, visit key landmarks like the Duomos, and enjoy a light lunch, with the option to add winery visits for an enhanced culinary experience.
-
The tour is wheelchair-accessible and stroller-friendly, catering to diverse traveler needs, and features a flexible itinerary to accommodate various preferences.
-
The tour has received excellent reviews, with 5-star ratings, highlighting the guides’ excellence, scenic views, and the overall enjoyment and memorability of the experience.
Tour Overview

This private tour from Florence to Cortona and Montepulciano provides an opportunity to explore two charming Tuscan towns at a leisurely pace.
With a rating of 5.0 from 9 reviews, this private tour offers a chauffeured drive through the picturesque Arno Valley.
Guests will have time to wander the cobblestone streets of Cortona and Montepulciano, taking in the sights and attractions.
Optional winery visits are available for an additional cost.
The tour includes hotel pickup and drop-off, a driver/guide, comfortable transportation, and a light lunch.
It’s an accessible experience suitable for most travelers, with wheelchair and stroller access, and infant seats available.
You can also read our reviews of more private tours in Florence
Inclusions

The private tour from Florence to Cortona and Montepulciano includes a comprehensive set of amenities to provide visitors with a comfortable and hassle-free experience.
The package includes:
- Hotel pickup and drop-off, ensuring a seamless start and end to the day.
- A knowledgeable driver/guide who’ll lead the tour and provide insights into the local history and culture.
- Transportation in a luxurious Mercedes-Benz V Class vehicle equipped with air conditioning and Wi-Fi, allowing travelers to enjoy the scenic drive in comfort.
Plus, the tour includes a light lunch, as well as all taxes, tolls, and parking fees, making it an inclusive and worry-free experience.
Accessibility and Additional Info
Wheelchair-accessible vans and stroller-friendly seating make this tour an inclusive option for travelers of all abilities.
Comfortable shoes are recommended to explore the historic towns at your own pace. The casual dress code ensures you can focus on enjoying the sights without worry.
Most travelers can participate, though infants may require additional seats. The tour provides flexibility, allowing you to make the most of your time in Cortona and Montepulciano.
Whether you’re seeking a leisurely stroll or a more active day, this private tour accommodates your preferences for a memorable experience.
Pickup Details

Guests can be picked up at a select location in Florence, such as their hotel, apartment, or villa, starting at 8:30 AM.
This tour offers free cancellation up to 24 hours before the experience, providing flexibility for travelers.
The pickup details include:
- Convenient locations across Florence, ensuring a seamless start to the tour.
- An 8:30 AM departure time, allowing ample time to explore Cortona and Montepulciano.
- Free cancellation up to a day before the tour, accommodating last-minute changes in plans.
The tour’s accessibility and flexibility cater to the needs of various travelers, making it a hassle-free and enjoyable experience.
Customer Reviews
What do the customer reviews say about this private tour from Florence to Cortona and Montepulciano? The reviews are overwhelmingly positive, with a 5-star rating across 9 reviews. Travelers consistently praise the excellence of the guides, the personalized service, and the flexibility to explore at their own pace. The scenic views and quality of food and wine also receive high marks. The tour highlights visitors’ appreciation for the beauty of the destinations, the knowledgeable drivers, and the overall experience. The reviews underscore this tour as an enjoyable and memorable way to discover the charming towns of Cortona and Montepulciano.
| Criteria | Rating |
|---|---|
| Guides | 5/5 |
| Overall Experience | 5/5 |
| Destinations | 5/5 |
| Service | 5/5 |
| Flexibility | 5/5 |
- Florence: Skip-The-Line Uffizi Gallery Timed Entry Ticket
★ 4.5 · 27,832 reviews - Florence: Timed Entrance Ticket to Michelangelo’s David
★ 4.6 · 16,983 reviews - Florence: Michelangelos David Skip-the-Line Entry Ticket
★ 4.5 · 12,764 reviews - Florence: Leonardo Interactive Museum Entry Ticket
★ 4.5 · 11,763 reviews - Florence: Pasta Cooking Class With Unlimited Wine
★ 4.9 · 10,285 reviews - Florence: Pisa, Siena, San Gimignano, and Chianti Experience
★ 4.5 · 8,393 reviews
Exploring Cortona
The private tour offers visitors the chance to enjoy the charming town of Cortona.
As the group explores this historic Tuscan gem, they’ll discover:
-
The stunning Piazza della Repubblica, the heart of Cortona, where they can admire the Renaissance architecture and soak in the lively atmosphere.
-
The Duomo of Cortona, an impressive cathedral dating back to the 12th century, with its intricate facade and impressive interior.
-
The Etruscan Museum, which houses a remarkable collection of artifacts that offer insights into the town’s ancient roots.
Throughout the tour, visitors can wander the picturesque streets, pop into local shops, and savor the authentic flavors of Cortona’s cuisine.
Visiting Montepulciano
After exploring the historic charms of Cortona, the private tour continues its journey to the captivating town of Montepulciano. As one of the most picturesque hilltop towns in Tuscany, Montepulciano offers a delightful array of Renaissance architecture, charming cobbled streets, and renowned wineries. Visitors can wander the Piazza Grande, admire the Duomo, and savor the region’s renowned Vino Nobile di Montepulciano. The tour provides ample time to discover the town’s highlights at your own pace, with options to visit local wineries for tastings and light lunches. The picturesque scenery and opportunity to take in Montepulciano’s timeless charm make this stop a true highlight of the private tour.
| Activity | Duration | Cost |
|---|---|---|
| Explore Piazza Grande | 30 minutes | Free |
| Visit Duomo | 45 minutes | Free |
| Winery tour and tasting | 1-2 hours | Varies |
| Lunch at a local restaurant | 1-2 hours | Varies |
| Stroll through the historic town center | 1 hour | Free |
Winery Visits

During the Montepulciano portion of the private tour, visitors have the opportunity to explore the renowned local wineries. The tour offers several optional winery visits, allowing guests to indulge in the region’s exceptional vintages.
Visitors can:
- Sample the acclaimed Vino Nobile di Montepulciano, a DOCG-designated red wine known for its complexity and elegance.
- Visit family-owned estates and learn about the centuries-old winemaking traditions that have shaped the character of Montepulciano’s wines.
- Enjoy guided tastings and, if desired, purchase bottles to take home, further enhancing the immersive experience of this private tour.
The winery visits provide a delightful complement to the exploration of Montepulciano’s historic streets and landmarks, offering a well-rounded taste of the region’s renowned culinary and oenological heritage.
Frequently Asked Questions
What Is the Duration of the Private Tour?
The tour duration is not explicitly stated in the overview. However, based on the included details such as hotel pickup, a light lunch, and exploration of two towns, the tour is likely a full-day experience.
Is Lunch Provided at a Specific Restaurant?
The tour includes a light lunch, though the specific restaurant is not mentioned. The tour provides a chauffeured drive, with the flexibility to explore at the traveler’s pace and options for winery visits along the way.
Are There Any Special Dietary Accommodations Available?
The tour includes a light lunch, but there’s no mention of any special dietary accommodations. Travelers with dietary restrictions should contact the tour provider in advance to see if they can accommodate their needs.
Can the Tour Be Customized to Include Additional Sights?
Yes, the tour can be customized to include additional sights. The driver/guide is flexible and willing to accommodate requests to visit other places of interest along the way, within the tour duration.
Is There an Option to Extend the Tour Duration?
Yes, the tour duration can be extended for an additional fee. The tour provider offers flexible options to customize the itinerary and accommodate travelers’ needs, allowing them to spend more time exploring the destinations.
Private Tour From Florence to CORTONA & MONTEPULCIANO
The Sum Up
This private tour from Florence offers a chance to discover the charming towns of Cortona and Montepulciano. Guests can admire the historic architecture, savor local cuisine, and enjoy optional wine tastings, all while experiencing the picturesque Tuscan countryside in the comfort of a private chauffeured vehicle. It’s an unforgettable way to take in the rich cultural and culinary heritage of this captivating region.




























