Florence to Pienza and Montepulciano: Private day trip
Private ride with a local driver
10hRound tripPrivate driver
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About your trip
Your journey begins in Florence, heading to Pienza, where Renaissance beauty and Tuscan charm await. Stroll through UNESCO-listed streets, sampling local pecorino while enjoying sweeping Val d'Orcia views. Next, continue to Montepulciano, with its ancient palazzos and renowned Vino Nobile. Immerse yourself completely in Tuscany's art, architecture, and flavors.
Exclusively yours: private vehicle and professional driver
Discover local insights you won't find in guidebooks
Experience the freedom to explore at your own speed
Perfectly planned for families, friends, or solo travelers
What to expect
Your day trip begins wherever you are
Meet our professional driver right where you prefer in Florence whenever suits you best. No time wasted getting to the pickup point, grab your bag and start your trip right away.Discover more with local expertise
Your driver’s local insights will set the tone for your day trip. A hidden café here, a must-try restaurant there; insider tips you’ll love sharing later. This isn’t a guided tour but your ride will be rich with stories and discoveries along the way. And throughout the day, your driver will be available for you as needed, ready to assist, happy to help, making your trip stress-free.Explore at your own pace
After arriving in Pienza, you'll have the freedom to explore its scenic balconies and pecorino shops at your own pace, before continuing on to Montepulciano, where you can taste local wines and see the historic palazzos. Throughout the day, your driver will stay close, available to help out, offer recommendations, or share local insights, before ensuring a comfortable return to Florence.
Perfect for any private group
Whether you're traveling solo, as a family with kids, or as a large group, this service is tailored for your comfort and flexibility. It's the ideal option especially if you have limited time or a busy schedule.Good to know
- Two-way private car transfer
- Air-conditioned vehicle
- Personalized pickup and drop-off
- Professional English-speaking driver
- Complimentary bottled water
- Free cancellation 24 hours before departure
- Entry/Admission tickets to paid attractions in Pienza and Montepulciano should be purchased separately unless specified otherwise
- Meals, snacks, and gratuity are not included
From €305
per person
Select date and travelers
Free cancellation up to 24 hours before your pickup time.
For a group of 1-3 travelersTotal€915
Your trip at a glance
Your trip at a glance
Start in Florence
You choose the pickup spot.
1
Pienza
Feel free to explore at your own pace and discover
Stop: 3 hours - admission not included






2
Montepulciano
Feel free to explore at your own pace and discover
Stop: 3 h 30 min - admission not included






Back to Florence
We’ll take you back to your starting point.
Duration of the stops can be changed upon request after booking
Have questions or need help?Contact our Customer Support. We are available 24/7
Daytrip is loved all around the world. Here's why.
Know more about your day trip
Pienza is considered the ideal Renaissance city created when Pope Pius II transformed his humble birthplace into a planned urban utopia in the 1450s. During your 3-hour visit explore the perfectly proportioned Piazza Pio II with its harmonious cathedral and Palazzo Piccolomini stroll the panoramic walkways offering breathtaking views over the Val d'Orcia's rolling hills and cypress trees and wander the charming streets with names like Love Street and Kiss Street. This UNESCO World Heritage site exemplifies Renaissance urban planning while maintaining an intimate village atmosphere.
During your 3.5-hour visit to Montepulciano, explore the grand Piazza Grande with its medieval Palazzo Comunale (climb the tower for panoramic views), visit the Renaissance-perfect San Biagio Church just outside the walls, and stroll the sloping Corso, the main street lined with noble palaces and wine shops. Don't miss entering at least one historic wine cellar built into the rock beneath the city, where Vino Nobile di Montepulciano ages in massive oak barrels. The town's position atop a limestone ridge offers spectacular vistas from various viewpoints along the walls.
Pienza is famous for its pecorino cheese, considered among Italy's finest sheep's milk cheeses. The area's unique microclimate and flora create distinctively flavored milk, resulting in pecorino ranging from fresh and mild to aged and sharp. During your visit, sample different aging stages at cheese shops along Corso Rossellino. Look particularly for pecorino sotto cenere (aged under ash) and the crosta nera (with a black rind). The cheese pairs perfectly with local honey, jam, or Montepulciano wine for an authentic Tuscan tasting experience.
Vino Nobile di Montepulciano is one of Tuscany's most prestigious wines, holding DOCG status (Italy's highest quality designation). Made primarily from Sangiovese grapes (locally called "Prugnolo Gentile") grown on Montepulciano's hillsides, it offers elegant fruit flavors, spice notes, and firm structure. The wine must age at least two years before release, with additional aging for Riserva wines. During your visit, taste the difference between Vino Nobile, Rosso di Montepulciano (its younger sibling), and Vin Santo (sweet dessert wine) at the historic cellars along the Corso.
Pienza and Montepulciano are approximately 120-150 kilometers (75-93 miles) southeast of Florence, with a driving time of about 1.5-2 hours to reach the area. The journey takes you through the stunning Tuscan countryside, past the rolling hills of Chianti, into the UNESCO-protected Val d'Orcia landscape with its iconic cypress trees and golden fields. Your private Daytrip driver handles all transportation, allowing you to relax and enjoy the changing scenery between locations.
Montepulciano offers unique wine tasting experiences in historic cellars beneath the city. For a comprehensive introduction, visit the Consorzio del Vino Nobile in the Palazzo del Capitano, offering tastings from multiple producers. For atmospheric experiences, enter the underground cellars of established wineries like Contucci, De' Ricci, or Talosa along the Corso. Most charge a small fee (€5-15) for tastings, often waived with purchase.
Spring (April-June) and fall (September-October) offer the most pleasant weather and spectacular landscapes. Spring brings verdant hills and wildflowers, while fall features harvest activities, golden light, and changing foliage. Summer provides long daylight hours but can be quite hot for hilltop exploration. Winter offers peaceful visits with few tourists, though some establishments may have reduced hours. Avoid midday arrival during summer months; your driver can plan morning or late afternoon visits to enjoy comfortable temperatures for exploring these elevated towns.
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Frequently Asked Questions
If you have any questions, here are the answers.Day trips offer travelers private round-trip transportation to popular sightseeing locations. One of our professional drivers will pick you up in a luxurious, climate-controlled car, take you to the site of interest, and wait for you while you explore before driving you back to your hotel.
Yes! You’re free to choose the pickup and drop-off times that work best for you. However, the time spent at the destination is fixed and cannot be changed.
Each sightseeing stop has a recommended duration that includes plenty of time to explore. However, it is possible to customize the time spent at each sightseeing stop at a later stage in the booking process to best fit your unique schedule.
Your Daytrip driver will wait for you nearby for the duration of your exploration, meaning you’ll never have to wait for your return trip transportation to arrive. Your comfort and convenience are our top priorities, and we aim to close out your day trip with a return on your schedule.
The price of a day trip does not include any entrance tickets, guided tours, or meals you may partake in at your destination. The price covers round-trip transportation in a luxury vehicle with a professional driver who can provide local insights en route.
Day trip bookings can be canceled up to 24 hours before your trip for a full refund, no strings attached. While the destination and stops are predetermined, it is possible to change your pick-up point, whether it is at your hotel or some other location within the city.
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