Set out on a private day trip from Florence to uncover the enchanting hilltop towns of Montalcino and Montepulciano. These Tuscan gems are renowned for their exquisite wines and captivating historical sites. With a dedicated driver/guide, you’ll customize your itinerary to learn about the region’s rich architectural heritage, savor local cuisine, and marvel at the breathtaking countryside. Discover the secrets that lie within these charming towns and uncover the reasons why they’ve captured the hearts of travelers from around the world.
Key Points

- This private day trip from Florence explores the historic hilltop towns of Montalcino and Montepulciano, known for their renowned Brunello and Vino Nobile wines.
- The customizable itinerary includes wine tastings, stunning views, and architectural discoveries, guided by a dedicated driver/guide for a personalized experience.
- Activities in Montalcino encompass a wine-tasting tour, a visit to the historic Rocco fortress, and exploration of Piazza del Popolo.
- In Montepulciano, guests can stroll through quaint streets, admire Renaissance-style palaces, and optionally participate in a wine tasting.
- The tour includes hotel pickup and drop-off, transportation by private vehicle, and all museum and monument entrance fees, ensuring a hassle-free experience.
Tour Overview and Highlights

This private full-day trip from Florence takes travelers to the renowned wine-producing areas of Montalcino and Montepulciano.
With a customizable itinerary and undivided attention from a guide, the tour allows visitors to explore these historic hilltop towns famous for their Brunello and Vino Nobile wines.
Travelers can enjoy wine tastings, admire stunning views, and discover the architecture and piazzas of both locations.
Travelers can savor wine tastings, marvel at breathtaking vistas, and uncover the architectural gems and piazzas of Montalcino and Montepulciano.
The tour includes hotel pickup, transportation, and the flexibility to focus on the interests of the group, ensuring an enriching and personalized experience in Tuscany’s picturesque countryside.
Here are more experiences we've reviewed in Florence
Itinerary and Activities

The journey begins with morning pickup from the traveler’s Florence hotel at 9:00 am.
Venturing through the Tuscan countryside, the tour showcases olive groves and vineyards along the way.
In Montalcino, the experience includes:
-
A wine-tasting tour (additional €10)
-
A visit to the historic Rocco fortress
-
Exploring the charming Piazza del Popolo
The afternoon is spent in Montepulciano, where the itinerary features:
-
A stroll through the quaint streets
-
Admiring the Renaissance-style palazzi
-
An optional wine tasting (additional €15)
Tour Inclusions
The tour includes bottled water, a dedicated driver/guide, hotel pickup and drop-off, and transportation by private vehicle.
Museum and monument entrance fees, as well as lunch and gratuities, are also covered. This ensures a hassle-free experience where you can focus on exploring the renowned wine regions of Montalcino and Montepulciano.
The private nature of the tour guarantees undivided attention from the guide, who can tailor the itinerary to your interests.
The private nature of the tour ensures personalized attention from the guide, who can customize the itinerary to your preferences.
With everything taken care of, you’re free to learn about the stunning landscapes, historical architecture, and world-class wine tastings that make this Tuscan adventure so special.
Additional Information
Confirmation of the booking is received upon completion, though availability may be subject to last-minute reservations.
This private tour ensures your group is the only participants. Additional amenities include:
-
Infant seats available for children
-
Not wheelchair accessible, but stroller accessible
-
Service animals allowed
-
Private vehicle transportation provided
-
Free cancellation up to 24 hours before the experience
This customizable tour allows you to tailor the itinerary based on your interests, with undivided attention from a knowledgeable guide throughout the day.
Reviews and Ratings
With a perfect rating of 5.0 across 3 reviews on Viator and Tripadvisor, this private day trip to Montalcino and Montepulciano has earned overwhelmingly positive feedback.
Reviewers praise the knowledgeable guide Marco, who tailors the experience to guests’ interests. The wine tastings and lunch were especially enjoyable.
One reviewer notes the "undivided attention" from the guide, while another appreciated the flexibility to customize the itinerary.
Guests also highlight the stunning scenery and historical architecture encountered in both towns.
The tour’s free cancellation policy up to 24 hours prior further adds to its appeal.
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
Discovering Montalcino
Montalcino, a renowned wine-producing town nestled in the heart of Tuscany, beckons visitors with its captivating history and world-famous Brunello wines.
Perched atop a scenic hilltop, the town’s medieval fortress, the Rocca, offers panoramic views of the surrounding vineyards and olive groves. Visitors can explore the charming Piazza del Popolo, lined with Renaissance-era palaces, and indulge in a wine-tasting tour to sample the region’s renowned Brunello di Montalcino.
Other highlights include:
-
Discovering the town’s historic cellars and production facilities
-
Hiking the trails that wind through the picturesque countryside
-
Visiting the Abbey of Sant’Antimo, a Romanesque architectural gem
-
Savoring the local cuisine, including hearty stews and artisanal cheeses
-
Browsing the quaint shops for local crafts and artisanal products
Exploring Montepulciano
What makes Montepulciano, another renowned Tuscan town, so captivating? With its picturesque Renaissance architecture, Montepulciano enthralls visitors.
Strolling through its narrow streets, one marvels at the impressive palaces, churches, and historic structures. The heart of the town is the Piazza Grande, dominated by the 16th-century Town Hall and the magnificent Duomo.
Oenophiles delight in sampling the area’s renowned Vino Nobile di Montepulciano, one of Italy’s premier red wines.
After exploring the town, guests can opt for an optional wine tasting to appreciate the full depth of this Tuscan gem’s vinous delights.
Customizing Your Experience
Beyond exploring the charming town of Montepulciano, this private day trip offers customizable experiences tailored to your interests.
Your knowledgeable guide is at your service to craft the perfect itinerary based on your preferences. You may choose to:
-
Delve deeper into the region’s winemaking heritage with additional tastings
-
Discover lesser-known sights and hidden gems off the beaten path
-
Linger longer in Montalcino or Montepulciano to soak up the atmosphere
-
Incorporate a scenic lunch stop in the countryside
-
Customize the start and end times to suit your schedule
With a private tour, the day is entirely yours to explore Tuscany at your own pace.
The Sum Up
This private day trip from Florence offers the opportunity to discover the charming hilltop towns of Montalcino and Montepulciano, known for their exceptional wines. With a customizable itinerary, visitors can enjoy the rich history, architecture, and local cuisine of these Tuscan gems, all while enjoying personalized attention and stunning countryside views. Whether seeking wine tastings, historic sites, or simply a leisurely stroll, this day trip promises an unforgettable experience.
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
