San Gimignano 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 San Gimignano, 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 San Gimignano 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 San Gimignano.
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 €362
per person
Select date and travelers
Free cancellation up to 24 hours before your pickup time.
For a group of 1-3 travelersTotal€1,086
Your trip at a glance
Your trip at a glance
Start in San Gimignano
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 San Gimignano
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
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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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