Tuscany’s rolling hills and picturesque vineyards have long captivated travelers. This private day trip from Florence offers a chance to explore two of the region’s most charming towns – Montalcino and Montepulciano. With a knowledgeable guide leading the way, you’ll explore the history and culture of these enchanting destinations. From sampling world-renowned wines to admiring historic landmarks, this all-inclusive tour promises an immersive Tuscan experience. Whether you’re a wine enthusiast or simply seeking to soak in the essence of this captivating region, this day trip could be the perfect addition to your Florence itinerary.
Good To Know
- This private day trip from Florence offers a guided exploration of the renowned wine regions of Montalcino and Montepulciano, including wine tastings and visits to historical sites.
- The full-day itinerary (9 am to 6 pm) includes hotel pickup/drop-off, private vehicle transport, entrance fees, bottled water, and a provided lunch, all for $1,192.61 for up to 7 people.
- In Montalcino, visitors can experience a 3-hour tour with an optional Brunello di Montalcino wine tasting, and explore historical landmarks like the Rocca fortress and Piazza del Popolo.
- The 3-hour visit to Montepulciano includes an optional tasting of Vino Nobile di Montepulciano and Rosso di Montepulciano wines, as well as a stroll through the town’s Renaissance-style streets.
- The tour also includes a brief 30-minute stop in the UNESCO-listed town of Pienza, known for its well-preserved Renaissance architecture and artisanal shops.
Tour Overview

This private day trip from Florence takes travelers to the charming towns of Montalcino and Montepulciano.
The full-day tour lasts from 9:00 am to 6:00 pm and costs $1,192.61 for up to 7 people. Participants receive hotel pickup and drop-off, bottled water, a driver/guide, and transport by private vehicle.
Entrance fees, lunch, and gratuities are also included. While the tour isn’t wheelchair accessible, infant seats and strollers are available.
Travelers can cancel up to 24 hours beforehand with no charge. With only your group participating, this personalized experience provides an in-depth exploration of the region’s scenic landscapes, historical sites, and renowned wines.
You can also read our reviews of more private tours in Florence
Itinerary Highlights

Departing from Florence at 9:00 am, the private day trip takes travelers through scenic landscapes of olive groves and vineyards before arriving in the medieval town of Montalcino.
Here, guests enjoy a 3-hour visit, including a wine-tasting tour for an additional €10 per person. They’ll also explore historical sites like the Rocco fortress and Piazza del Popolo.
Next, the group heads to Montepulciano, where they’ll stroll through Renaissance-style streets and have the option to taste the renowned Vino Nobile di Montepulciano and Rosso di Montepulciano wines for an additional €15 per person.
The tour also includes a brief visit to the UNESCO-listed town of Pienza.
Montalcino Exploration
After exploring the scenic countryside en route, guests arrive in the medieval town of Montalcino.
They’ll spend 3 hours here, starting with a wine-tasting tour. Guests can sample the renowned Brunello di Montalcino, one of Italy’s finest red wines.
Then, they’ll have time to wander the historical streets and visit iconic sites like the Rocca fortress and Piazza del Popolo.
This charming hilltop town offers stunning views of the surrounding Tuscan vineyards and olive groves.
With its well-preserved Renaissance architecture, Montalcino provides an authentic glimpse into Italy’s past, complementing the wine-tasting experience.
Montepulciano Adventure
The group then continues their journey to the historic town of Montepulciano, a renowned center of wine production.
Here, they’ll spend 3 hours strolling through the Renaissance-style streets and exploring the town’s rich history and culture. An optional wine tasting of the famous Vino Nobile di Montepulciano and Rosso di Montepulciano wines is available for an additional €15 per person.
Guests can also visit the iconic Piazza Grande and admire the stunning architecture that has earned Montepulciano the designation as a UNESCO World Heritage Site.
After their Montepulciano adventure, the group will spend 30 minutes in the nearby town of Pienza before returning to Florence.
Pienza Visit
The group then proceeds to the nearby UNESCO-listed town of Pienza, spending 30 minutes exploring its historic streets and architecture.
Pienza is renowned for its well-preserved Renaissance-era structures, including:
- The Pienza Cathedral, a magnificent example of Renaissance architecture
- The Palazzo Piccolomini, a stately palace with a beautiful inner courtyard
- The iconic Piazza Pio II, the town’s central square lined with historic buildings
- Artisanal shops and boutiques offering local delicacies, handicrafts, and wine.
Though the visit is brief, it allows the group to soak in the charming ambiance of this picturesque Tuscan town before continuing on to their next destination.
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Inclusions
This private day trip from Florence to Montalcino and Montepulciano includes several key services to enhance the experience.
Bottled water is provided, and a knowledgeable driver/guide accompanies the group throughout the day. Hotel pickup and drop-off, as well as transportation by private vehicle, are included.
Entry fees to museums and monuments are covered, ensuring seamless access to the historical sites. A delicious lunch is also part of the package, along with gratuities, making this a truly all-inclusive experience.
With these comprehensive inclusions, guests can focus on seeing the beauty and traditions of the Tuscan countryside without worrying about additional costs.
Accessibility and Additional Details
Infant seats are available for this tour, making it accessible for families.
The tour isn’t wheelchair accessible, but strollers are permitted.
Service animals are allowed to accompany guests.
Most travelers can participate in this experience, with the confirmation received at the time of booking unless within 3 days of travel.
- Infant seats available
- Not wheelchair accessible, but stroller accessible
- Service animals allowed
- Most travelers can participate
Guest Reviews and Feedback
Guests who’ve experienced this private day trip have provided overwhelmingly positive reviews, awarding it a remarkable 5.0-star overall rating.
Travelers praised the knowledgeable and planning skills of driver Marco, who expertly guided them through the scenic landscapes and historic sites. Highlights included the enjoyable wine tastings, a delicious lunch, and the personalized experiences in both Montalcino and Montepulciano.
One guest remarked that the tour exceeded their expectations, allowing them to fully enjoy the charm and beauty of these Tuscan towns.
The combination of the carefully curated itinerary and the attentive service resulted in a truly memorable day trip from Florence.
Frequently Asked Questions
Can I Customize the Tour Itinerary?
The tour itinerary can be customized to suit your preferences. You can discuss your specific interests with the provider and they’ll work with you to tailor the experience to your needs.
Is There an Option to Add Additional Stops?
Yes, the tour can be customized to include additional stops. Travelers can discuss their preferences with the tour provider and see if they can accommodate any special requests within the allotted time and budget.
What Is the Average Group Size for This Tour?
The tour is a private experience for your group only, with no other participants. The tour operator does not disclose the average group size, but notes that the tour accommodates up to 7 people.
Can I Request a Different Pickup/Drop-Off Location?
Yes, you can request a different pickup or drop-off location. The tour provider offers flexible arrangements and will work with you to accommodate your needs, as long as the location is within the tour area.
Are Any Discounts Available for Larger Groups?
Yes, discounts are available for larger groups. The tour price starts from $1,192.61 per group (up to 7 people), so booking for a bigger group could result in a lower per-person cost.
Private Day Trip to Montalcino and Montepulciano From Florence
The Sum Up
This private day trip offers the perfect opportunity to take in the enchanting landscapes and rich history of Tuscany. Travelers can explore the charming towns of Montalcino and Montepulciano, indulge in optional wine tastings, and enjoy a brief stop in the UNESCO-listed Pienza. With personalized service and an expert guide, this all-inclusive tour guarantees an unforgettable experience.




























