Private Montepulciano & Pienza Day Trip from Florence

Florence , Italy

Private Montepulciano & Pienza Day Trip from Florence

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For a full refund, cancel at least 24 hours before the scheduled departure time.

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About this experience

Experience Tuscany on a private full-day Montepulciano and Pienza tour from Florence, traveling in comfort with an English-speaking chauffeur in a luxury Mercedes-Benz vehicle.

This itinerary combines medieval towns, world-class wine, and iconic Tuscan food traditions. Explore the elegant streets of Montepulciano, enjoy a winery visit featuring the renowned Vino Nobile di Montepulciano, and continue through the Val d’Orcia for a cheese tasting and lunch centered around Pecorino di Pienza.

Unlike group tours, this experience is fully private and customizable, offering door-to-door service, relaxed pace, and the flexibility to adapt the day to your interests. While visits are unguided, your chauffeur will share local knowledge, history, and cultural insights throughout the journey.

Operated by Best Rome Driver, a trusted Italian company with nearly 20 years of experience, this tour guarantees reliability, professionalism, and a high standard of service throughout your day in Tuscany.

Available options

Private Montepulciano & Pienza Day Trip from Florence

Pickup included

What's included

Winery and cheese factory reservations

Private English-speaking chauffeur

Fully customizable private itinerary

Luxury Mercedes-Benz sedan or van

Pickup and drop-off from any Florence location

Detailed itinerary

Pickup directly from your accommodation or preferred location in Florence.

Meet your English-speaking chauffeur, who will be at your disposal for the full day in a luxury Mercedes-Benz sedan or van. During the drive, your chauffeur will share historical context, local traditions, and insights into the Tuscan countryside you’ll be crossing.

Arrive in Montepulciano, a stunning hilltop town known for its Renaissance palaces, stone streets, and sweeping views over the Val d’Orcia.

You’ll have time to stroll through the historic center, explore small shops, and enjoy the atmosphere of one of Tuscany’s most elegant wine towns.

Highlights you may see include : Piazza Grande, Historic palazzos and noble residences, Panoramic viewpoints over the countryside

After the town visit, meet your driver and continue to a local winery just outside Montepulciano. Here you’ll enjoy a tasting of the area’s most famous wines, including Vino Nobile di Montepulciano, produced from Prugnolo Gentile grapes and known for its structure, elegance, and aging potential.

The tasting is typically accompanied by local products such as olive oil or light Tuscan appetizers.

Note : Wine tasting is not included and is paid directly at the winery. We reserve the visit in advance.

Continue through the rolling hills of the Val d’Orcia to the Pienza countryside, where you’ll stop at a traditional local cheese factory.

Here you can enjoy a tasting and lunch centered around Pecorino di Pienza, one of Tuscany’s most celebrated sheep’s-milk cheeses, often paired with honey, jams, cured meats, and local wine.

Pienza is known all over the world for its production of 'pecorino cheese' and for its traditional Tuscan cuisine.

Note : Tasting and lunch are not included and are paid directly on site. Reservations are arranged in advance.

In the afternoon, your chauffeur will take you into Pienza itself, a UNESCO World Heritage town designed during the Renaissance as an “ideal city.” Enjoy free time to stroll through its elegant streets, artisan shops, and scenic terraces overlooking the Val d’Orcia.

Highlights you may see include : Piazza Pio II, Pienza Cathedral, Panoramic viewpoints over the Val d’Orcia

Relax during the scenic drive back to Florence, with drop-off at any location of your choice.

What's not included

Private Licensed Tour Guides

Wine tasting fees

Cheese tasting and lunch

Gratuities (optional)

Available languages

Guide guide

EN IT

Reviews breakdown

Tripadvisor 5.0

8 reviews

5★

4★

3★

2★

1★

Important information

Wheelchair accessible

Infants and small children can ride in a pram or stroller

Service animals allowed

Specialized infant seats are available

Suitable for all physical fitness levels

Foldable wheelchairs only, which must fit in the vehicle trunk

Guests has to be able to get in and out of the vehicle independently

About Florence

Florence, the capital of Italy's Tuscany region, is a treasure trove of art, architecture, and history. Known as the birthplace of the Renaissance, it's home to iconic masterpieces, stunning cathedrals, and a rich cultural heritage that continues to captivate visitors from around the world.

Top Attractions

Duomo

The Florence Cathedral, known as the Duomo, is a masterpiece of Renaissance architecture. Its iconic dome, designed by Brunelleschi, offers panoramic views of the city.

Architecture/Religious 2-3 hours Free to enter the cathedral, €18 for the climb to the dome

Uffizi Gallery

One of the world's most famous art museums, the Uffizi Gallery houses works by Botticelli, Michelangelo, and Leonardo da Vinci.

Museum/Art 2-3 hours €20

Ponte Vecchio

A medieval stone bridge famous for its jewelry shops. It's one of the most iconic landmarks in Florence.

Architecture 30 minutes to 1 hour Free

Piazzale Michelangelo

A panoramic terrace offering breathtaking views of Florence. It's a perfect spot for sunset and photography.

Scenic Viewpoint 1-2 hours Free

Accademia Gallery

Home to Michelangelo's famous statue of David, the Accademia Gallery is a must-visit for art lovers.

Museum/Art 1-2 hours €16

Must-Try Local Dishes

Bistecca alla Fiorentina

A thick-cut, grilled T-bone steak, seasoned simply with salt and pepper. It's a must-try for meat lovers.

Dinner Contains beef, not suitable for vegetarians or vegans

Ribollita

A hearty vegetable and bread soup, traditionally made with leftover bread and vegetables. It's a classic Florentine dish.

Lunch/Dinner Vegetarian, can be made vegan

Lampredotto

A Florentine street food made from the fourth and final stomach of a cow. It's typically served in a sandwich.

Lunch Contains beef, not suitable for vegetarians or vegans

Cantucci

Almond biscotti traditionally served with Vin Santo, a sweet Tuscan wine. They are crunchy and perfect for dipping.

Dessert Contains almonds, can be made gluten-free

Popular Activities

Hiking in the Tuscan countryside Cycling tours Hot air balloon rides Wine tasting tours Spa day at a luxury hotel Strolling through the gardens of Villa medici Visiting museums and art galleries Attending opera or concerts

Best Time to Visit

April to June, September to October

These months offer pleasant weather and fewer crowds compared to the summer peak. Ideal for sightseeing and outdoor activities.

15-28°C 59-82°F

Practical Information

Language

Official: Italian
Widely spoken: English, French, Spanish
English: Moderately spoken

Currency

Euro (EUR)

Time Zone

GMT+1 (CET), GMT+2 (CEST during daylight saving time)

Electricity

230VV, 50HzHz

Safety Information

Overall Safety Rating: Generally safe

Florence is generally safe for tourists, but pickpocketing and petty theft can occur, especially in crowded areas. Be aware of your surroundings and take precautions to protect your belongings.

Important Precautions:

• Keep valuables secure and out of sight
• Be cautious of your surroundings, especially in crowded areas
• Use licensed taxis or ride-sharing apps

Getting there

By air

Florence Airport • 5 km from city center
Pisa International Airport • 85 km from city center

By train

Santa Maria Novella Station

By bus

Villa Costanza Bus Station, Florence Airport Bus Terminal

Getting around

Public transport

The bus network covers the entire city and is the primary mode of public transport. Buses are frequent and reliable.

Taxis

Available • Apps: MyTaxi, FreeNow

Rentals

Car, Bike, Scooter

Neighborhoods

Santa Maria Novella Oltrarno San Lorenzo Santa Croce

Day trips

Siena

70 km from Florence • Half day to full day

A medieval city known for its stunning Piazza del Campo and the Palio, a traditional horse race held twice a year.

Pisa

85 km from Florence • Half day

Home to the iconic Leaning Tower of Pisa, this city offers a mix of historic sites and scenic views.

Chianti Wine Region

30-50 km from Florence • Full day

A picturesque wine region known for its rolling hills, vineyards, and charming villages.

Festivals

Festa di San Giovanni • June 24 Calcio Storico Fiorentino • June (dates vary) Firenze dei Fiori • April to June

Pro tips

Visit major attractions early in the morning or late in the afternoon to avoid crowds
Book tickets for popular attractions in advance to save time and avoid long queues
Explore the city's hidden gems, such as the Oltrarno neighborhood and the secret passages of the Palazzo Vecchio
Try local specialties like Bistecca alla Fiorentina, Ribollita, and Lampredotto
Learn a few basic Italian phrases to enhance your experience and connect with locals