Setting out on a private day trip from Florence to the enchanting Tuscan towns of Montepulciano and Siena is an opportunity to take in the region’s rich history and captivating scenery. With comfortable transportation and a knowledgeable local driver, this flexible tour promises a memorable journey filled with architectural marvels, renowned wines, and breathtaking vistas. From exploring Montepulciano’s medieval charm to admiring Siena’s iconic landmarks, this day trip offers a chance to discover the essence of Tuscany. What awaits those who embark on this captivating adventure?
Key Points

- Explore the historic hilltop towns of Montepulciano and Siena on a private day trip from Florence, traveling through the picturesque Tuscan countryside.
- Discover the medieval architecture, renowned wines, and panoramic views in Montepulciano, with the option to climb the bell tower.
- Experience the iconic Piazza del Campo and Gothic cathedral in Siena, with the possibility of climbing the cathedral’s bell tower.
- Enjoy the comfort and flexibility of a private air-conditioned vehicle with a local driver providing information, but not acting as a licensed guide.
- Customize the tour with additional stops or transfers, while bottled water is provided to keep you hydrated throughout the day.
Overview of the Private Day Trip

The private day trip from Florence to Montepulciano and Siena allows visitors to journey through the picturesque Tuscan countryside in the comfort of an air-conditioned vehicle.
Along the way, guests will explore the historic hilltop town of Montepulciano, renowned for its wine and architecture.
The tour then continues to Siena, where travelers can marvel at the city’s medieval square and Gothic cathedral, with an option to climb for panoramic views.
Throughout the day, a local driver is on hand to provide information and assistance, though they aren’t a licensed guide.
Food and drinks aren’t included in the tour.
Here are more experiences we've reviewed in Florence
Exploring Montepulciano

Visitors to Montepulciano can’t help but be captivated by the town’s charming medieval architecture and its reputation as a premier wine destination. Cobblestone streets wind up the hillside past Renaissance palaces, churches, and wine cellars. Exploring the historic center, travelers can admire the Piazza Grande and the impressive Duomo. A highlight is climbing the bell tower for panoramic views of the Tuscan countryside. Afterward, visitors can sample the region’s famous Vino Nobile di Montepulciano at one of the many enotecas or cantinas.
| Montepulciano Highlights | Description |
| — | — |
| Historic Architecture | Charming medieval and Renaissance buildings |
| Vino Nobile di Montepulciano | Premier local wine, known for its quality |
| Panoramic Views | Scenic vistas from the bell tower |
Discovering Siena

After exploring the charming medieval architecture and renowned wine of Montepulciano, the journey continues to the captivating city of Siena.
The group will visit Siena’s famous medieval square, the Piazza del Campo, and admire its impressive Gothic cathedral. Visitors can opt to climb to the top of the cathedral’s bell tower for panoramic views over the city and the surrounding Tuscan countryside.
The driver will provide information and recommendations, though a licensed guide isn’t included. With ample time to wander, travelers can enjoy Siena’s historic ambiance and vibrant atmosphere.
Transportation and Comfort

Comfortably traversing the picturesque Tuscan landscape, the private vehicle transports guests from Florence to the charming towns of Montepulciano and Siena. The air-conditioned vehicle ensures a smooth and comfortable journey, allowing travelers to sit back and enjoy the scenic countryside. Bottled water is provided, keeping guests hydrated throughout the day. The local driver offers helpful information, though not as an official guide, providing an insider’s perspective on the region. The private nature of the tour allows for flexibility, enabling guests to customize their experience with additional stops or transfers as desired.
| Feature | Description |
| — | — |
| Vehicle | Air-conditioned private vehicle |
| Amenities | Bottled water provided |
| Guide | Local driver offers information |
| Flexibility | Options for customized stops |
Inclusions and Exclusions

The day trip package includes an air-conditioned private vehicle, all necessary taxes and fees, and bottled water for guests.
A local driver is available to provide information, though they aren’t a licensed guide. Food and drinks, aside from the bottled water, aren’t included in the package price.
Guests can request additional private transfers or sightseeing stops, which may incur extra charges. The trip is accessible, with infant seats available and the option for service animals.
Most travelers can participate, as this is a private tour tailored to your group’s needs.
Prefer keeping things personal? Here are more private experiences we've reviewed in Florence
- Florence Private Tour With a Local – Highlights & Hidden Gems
- Cinque Terre and Pisa Tower Tour From Florence Semi Private
- Private Day Trip Tuscany Landscape and Wine Tasting From Florence
- PALAZZO VECCHIO Private Tour in Florence
- Private Full Day Walking Tour of Florence Highlights With Uffizi and Accademia
- Private Photo Tour in Florence With a Professional Photographer
Pickup and Meeting Details

Where would you like to be picked up for the day trip?
The English-speaking driver will meet you at the chosen location at your preferred time.
You’ll have a few options:
-
Select a centrally located hotel or apartment in Florence.
-
Choose a train station or public transit hub for easy access.
-
Opt for a private residence or other address of your convenience.
-
Discuss any additional private transfers or sightseeing stops you’d like along the way.
The driver will be there, ready to whisk you away on your private journey through the Tuscan countryside.
Accessibility and Additional Information

Infant seats are available for those traveling with young children, and service animals are permitted on the tour.
The tour is near public transportation and is stroller and wheelchair accessible, making it suitable for a wide range of travelers.
Most you can participate in this private tour, which is tailored to your group.
With flexible options for additional transfers or sightseeing stops, the tour can be customized to your preferences.
Whether you’re looking for a memorable day trip or an accessible way to explore Tuscany, this private tour offers a convenient and comfortable experience.
Frequently Asked Questions

Can the Itinerary Be Customized for Our Preferences?
The trip itinerary can be customized to match travelers’ preferences. Additional private transfers or sightseeing stops are available upon request to create a personalized day trip experience.
How Much Time Do We Have for Independent Exploration?
The trip allows for "ample time" for independent exploration in both Montepulciano and Siena. The driver can provide suggestions on how to make the most of this time based on your interests.
Will the Driver Provide Recommendations for Local Cuisine?
The driver can provide recommendations for local cuisine in Montepulciano and Siena. They have knowledge of the area and can suggest authentic regional dishes and dining options to enhance your independent exploration during the tour.
Is There an Option to Include a Licensed Guide?
No, the private day trip does not include a licensed guide. However, the local driver can provide some information and recommendations during the journey. Optional private guide services may be available for an additional fee upon request.
Can We Make Any Additional Stops Along the Way?
Yes, the tour offers options for additional private transfers or sightseeing stops along the way. Passengers can customize the itinerary to include other Tuscan towns or attractions of interest during the day trip.
The Sum Up
This private day trip from Florence to Montepulciano and Siena offers a captivating blend of Tuscan history, culture, and stunning scenery. Travelers can explore the medieval architecture of Montepulciano, taste its renowned Vino Nobile, and discover the iconic Piazza del Campo in Siena. With comfortable transportation and a knowledgeable local driver, this flexible tour provides a memorable and convenient way to experience the best of Tuscany.
More Guided Tours in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Florence Old City Street Food Tour and Guided Sightseeing
- Santa Maria del Fiore Cathedral tickets and Audio guide
- Florence: Uffizi Gallery Tickets with Optional audio guide
- Florence: Highlights Walking Tour with Expert Guide
- Florence: 2.5 hour Audio Guided Walking Tour led by Host
More Tours in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
- Florence Medici Bike Tour Cycle Through History and Power
More Tour Reviews in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence: Tuscan Cheese and Wine Tasting Experience
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
Still browsing? Here are more Florence experiences we've covered recently
- What Are The Best 2-Hour Tours In Florence? Our Top 3 Picks
- Our Picks For The 13 Best Wine Tours In Florence
- The 12 Most Popular Workshops & Classes In Florence
- The 11 Best Dining Experiences In Florence
- 14 Best Tours In Florence
- Florence’s 10 Best Dinner Experiences (With Prices & Reviews)
- 14 Best Walking Tours In Florence (With Prices)
- Florence’s 3 Best Hiking And Trekking Tours
- 7 Must-Try Private Driver Services In Florence
- Florence’s 14 Top Food Tours
- 14 Of The Best Photography Experiences In Florence
- Our Picks For The 13 Best Pasta Experiences In Florence
