How do day trips with Daytrip work?

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.

Will I have to wait around for the driver to return?

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.

Can I customize the pickup and drop-off times?

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.

Are entrance tickets and tours included in the price?

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.

How long will I have to explore?

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.

If my plans change, is the booking flexible?

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.

Can I take a large group?

Yes! Day trips are fully customizable to suit the needs of any private group. From solo travelers to large families with children and even corporate groups, we are ready to create a bespoke itinerary that accommodates parties of all sizes. The price is dependent on the number of vehicles required to serve your group, and we also provide child seats.

Will my driver speak English?

Your friendly, professional, local driver will speak English. Our drivers are happy to provide any local insight they can on the way to your destination and may be able to answer questions and provide tips for the best possible experience on your day trip.

Can I request children’s car seats for the journey?

Yes, we provide car seats for children of all ages, which meet stringent safety standards and local legal requirements. You can even bring your own car seat. We also have handicapped-accessible vehicles available for a wide range of needs for our passengers. When booking your day trip, please specify the accommodations you will need.

Can I pay securely online?

Yes, Daytrip offers flexible payment options. We accept Google Pay, Apple Pay, and Ali Pay. You also can pay securely online with any major credit card, such as Visa, Mastercard, or American Express.

Booking your day trip is as easy as our one-way and return trips! On the landing page of the day trip you’d like to take, simply select the date, pick up time, and how many adults and children will be on the trip. On the second page, you’ll fill in personal details, including any special requests, disability accommodations, and children’s car seats you may need. We are flexible too! You can change your exact pick-up location (hotel address, etc) up to 24 hours before your day trip.

Day trips Countries Italy SienaSiena to Pienza: Private day trip

Siena to Pienza: Private day trip

Scenic view of Siena - private day trip from Siena - photo 1

Scenic view of Siena - private day trip from Siena - photo 2

Scenic view of Siena - private day trip from Siena - photo 3

Scenic view of Siena - private day trip from Siena - photo 4

1 / 4

Private ride with a local driver

4h 45m

Round trip

Private driver

Trusted by 2+ million happy travelers across 120 countries

4.9

Tripadvisor Travelers’ Choice 2026

4.9

5176
Reviews

About your trip

Discover Pienza at your own pace! Your smooth ride to Pienza brings you to Pope Pius II's utopian vision of urban planning. Explore the harmonious Piazza Pio II, discover the magnificent Palazzo Piccolomini, and enjoy spectacular views over the Val d'Orcia while sampling the town's famous pecorino cheese. After a day of Renaissance perfection and Tuscan flavors, you'll enjoy a comfortable journey back, carrying the ideal spirit of Pienza with you.

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

From €169

Private group ride

per person

Select date and travelers

Free cancellation up to 24 hours before your pickup time.

For a group of 1-3 travelersTotal€552

What to expect

Your day trip begins wherever you are

Meet our professional driver right where you prefer in Siena 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

Once at Pienza, you'll have the freedom to explore this UNESCO World Heritage town and its Renaissance architecture at your leisure. Meanwhile, your driver will wait for you nearby, ensuring a stress-free return trip.

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 Pienza should be purchased separately unless specified otherwise
Meals, snacks, and gratuity are not included

From €169

Private group ride

per person

Select date and travelers

Free cancellation up to 24 hours before your pickup time.

For a group of 1-3 travelersTotal€552

Your trip at a glance

Start in Siena

You choose the pickup spot.

Pienza

Feel free to explore at your own pace and discover

Stop: 2 h 30 min - admission not included

Itinerary stop at Pienza on private day trip from Siena

Main attractions

A Renaissance ideal city in miniature — Pope Pius II rebuilt his birthplace village in 1459 as a model of humanist urban planning, commissioning Bernardo Rossellino to create a cathedral, papal palace, town hall and bishop's residence around a single perfectly proportioned piazza in just three years; the result is the purest expression of Renaissance civic ambition surviving in Italy
The view from the cathedral terrace south across the Val d'Orcia — rolling clay hills, isolated farmhouses and cypress avenues dissolving into a pale Tuscan horizon — is among the most painted and photographed landscapes in the world

What to eat

Pecorino di Pienza — sheep's milk cheese aged in walnut leaves, vine ash or clay — bought directly from the aged cheese shops lining Corso Rossellino; paired with local Brunello or Rosso di Montalcino

Back to Siena

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.

5.0

5176 reviewson Tripadvisor

4.9

991 reviewson Trustpilot

Amazing driver experience

Our driver, Ibrahim, was wonderful. He drove us from Amman airport to Petra. Our flight was one hour early and he was already waiting for us when we got to the exit of the airport. He was helpful, professional and friendly. We would definitely love to have Ibrahim again and highly recommend him!

Heidi IFebruary 27, 2026

Awesome experience! Highly recommend!

So, so happy I stumbled upon this website to book two private transports while visiting Lima, Peru. They were both one-way trips approximately 3 hours in length. Great communication as soon as everything was booked via email and I then downloaded their app. I had a few issues with the app and the customer service was awesome trying to assist me in getting it corrected. Honestly impressive customer service which gave you a positive feeling that you made the right choice. Both drivers were right on time - No issues whatsoever! Can't say enough about the service and ease of everything when travelling so far away. Great job to the daytrip team! Would strongly recommend.

okopFebruary 19, 2026

Touring through Tuscany

We had the same driver for our 2 day trip in tuscany. I was able to develop my own itinerary so I could go where we wanted and see the things we wanted. Marco was fantastic!! He opened doors for us and made sure my mother was able to get in and out of the car easily. He had water in the car for us. He was early picking us up both days and brought us as close to the towns as he could. He told us which way to go to enter the cities and then sent me his location so we knew how to get back to him after traveling the streets. Im so happy I decided to get a driver to take us through Tuscany. It took all the worry and anxiety of driving through this region I had never been to and didnt know where to park. Money well spent!

Melissa FFebruary 10, 2026

Great transfer option.

I used this service for a transfer from Split in Croatia to Perast Montenegro. My experience was exceptional. My driver Bojan was helpful, informative and ensured my journey was comfortable and enjoyable. I highly recommend the service.

Robyn COctober 2, 2025

It was a fantastic trip.

We were extremely satisfied with the quality of service we received from Day Trip. We had two Day Trip rides on August 31 from Athens to Lefkada and September 7 from Lefkada back to Athens. Both trips included stops at scenic sites in Greece. Both drivers were excellent and accommodating. However, we’d especially like to recognize Panos Peppas, who was our driver from Lefkada to Athens. Panos was incredibly nice & pleasant and delivered outstanding customer service, which included handling all of luggage, providing us with cold waters throughout the trip, providing us protein bars, providing us with printed materials on the Corinth Canal (one of scenic stops), looking up and providing us with terminal & gate info for our flight back home and providing us with a recipe for tzatziki.

Daydream20046758137September 20, 2025

Best transport company anywhere

We absolutely love this company and have used it many times over the years to get from A to B without the hassle of hiring a car ourselves. Excellent drivers every time. Efficient and professional. It’s worth every penny and we can honestly recommend Day Trip to everyone. It’s 5 star rating is well deserved.

Mary LSeptember 15, 2025

Excellent experience in traveling

We traveled from Nuremberg to Munich in a beautiful Audi. Driver picked us at our hotel at the exact time requested. Got us to Munich in plenty of time for our next tour. Driver made sure we were comfortable

Steve NAugust 20, 2025

Reasonably Priced and Safe Transportation

Gonzalo from daytrip was our driver and he was absolutely amazing. He went over and beyond trying to locate us as our service wasn't so good on our phones. He patiently awaited our arrival to the lobby so he could take us from Tulum Dreams Resort to our other hotel in cancun an hour and a half away near the airport prior to our departure flight home. He was polite, respectful and kind. Made sure we were comfortable during our long ride. Fast and to the point. I recommend this company as finding a one way ride from Tulum to Cancun isn't easy or cheap and this company provides a great service for a great price. I will definitely be using them again whenever I'm in the Cancun/Tulum area. Thank you DayTrip and Gonzola.

COCOApril 22, 2025

Daytrip never disappoints

We were picked up by Marianna to drive us from Heraklion to Chania. The weather was terrible & due to this Marianna arrived a few minutes late. She contacted me to advise of this. Marianna lives in Chana and she made our trip very interesting by informing us of local things to do and see in Chania. Marianna is a safe driver and we all felt comfortable with the speed she drove at and how good her driving was in heavy rain. She is a lovely person with fluent English. We highly recommend Daytrips and if you are in Heraklion or Chania please make sure you ask for Marianna.

5-star customer review for Daytrip private driver and tour services

Julie MApril 2, 2025

Great driver in Egypt

Used the service to go from Luxor to Hurghada, Egypt. Ahmed H was our driver and he was perfect. The car was new, clean, he had water and snacks for us, and accommodated our stops. Great service from him and would recommend it.

Maps315861February 28, 2025

See more reviews

Know more about your day trip

Pienza is small and compact, so 2 to 3 hours is usually enough to explore the historic center, sample pecorino, and enjoy the views. If you have flexibility, the surrounding Val d'Orcia offers other rewarding villages such as Montalcino and Montepulciano. For this specific Siena to Pienza trip, the focus stays on Pienza itself and the journey across the Val d'Orcia.

Pienza is about 33 miles (53 km) from Siena, with a drive of approximately 1 hour to 1 hour 15 minutes. The route crosses the heart of the Val d'Orcia, a UNESCO World Heritage landscape of rolling clay hills, isolated farmhouses, and cypress avenues that has shaped Tuscan painting for centuries.

Yes, both the historic center of Pienza and the surrounding Val d'Orcia landscape are UNESCO World Heritage Sites. Pienza was recognized in 1996 as the first application of Renaissance humanist urban planning, while the Val d'Orcia was added in 2004 for its cultural landscape that has influenced art and aesthetics across centuries of European history.

Yes, Pienza's historic center is fully pedestrianized and very compact. The main street, Corso Rossellino, runs the length of the village in just a few hundred meters, connecting Piazza Pio II to the panoramic terraces. Cobblestone surfaces are gentle, and the village can be explored at a relaxed pace, with frequent stops for cheese shops, cafes, and viewpoints.

Pienza is celebrated as a Renaissance ideal city in miniature. Pope Pius II rebuilt his birthplace village in 1459 as a model of humanist urban planning. Architect Bernardo Rossellino designed a cathedral, papal palace, town hall, and bishop's residence around a single perfectly proportioned piazza. Pienza is also the home of pecorino di Pienza, an exceptional aged sheep's milk cheese.

Pecorino di Pienza is a sheep's milk cheese aged in walnut leaves, vine ash, or clay, with a distinctive flavor that varies by aging method. The aged-cheese shops along Corso Rossellino, the main street, offer tastings and pairings with local Brunello di Montalcino or Rosso di Montalcino wines. Buying directly from these shops is the freshest option.

The terrace beside the cathedral offers what is widely considered one of the most painted and photographed views in the world. Looking south, the Val d'Orcia unfolds in waves of clay hills, lone farmhouses, and cypress avenues fading into the Tuscan horizon. Sunrise and the golden hour before sunset produce especially dramatic light.

Spring (April to June) and fall (September to October) are ideal, with mild weather, green or golden hills, and quieter streets. Summer is hot and busier with festivals and outdoor dining. Winter is cool and atmospheric, with fewer travelers and dramatic mist over the Val d'Orcia, though some shops keep shorter hours during the off-season.

Siena to Pienza: Private day trip

Private ride with a local driver

About your trip

What to expect

Your day trip begins wherever you are

Discover more with local expertise

Explore at your own pace

Perfect for any private group

Good to know

Your trip at a glance

Your trip at a glance

Daytrip is loved all around the world. Here's why.

Know more about your day trip

Explore similar trips from Siena

Frequently Asked Questions

More Day Trips

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