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 Montepulciano and Pienza: Private day trip

Siena to Montepulciano and Pienza: Private day trip

1 / 4

Private ride with a local driver

7h 15m

Round trip

Private driver

Trusted by 1+ million happy travelers across 120 countries

4.9

Tripadvisor Travelers’ Choice 2024

4.9

5176
Reviews

About your trip

Taste the soul of Tuscany: robust reds in Montepulciano and savory pecorino in Pienza for an indulgent feast for senses and sight!

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 €229

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€687

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

After arriving in Montepulciano, you'll have the freedom to explore its vineyards and historic center before continuing on to Pienza, where you can walk the panoramic terraces and sample local cheeses, all 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 Montepulciano and Pienza should be purchased separately unless specified otherwise
Meals, snacks, and gratuity are not included

From €229

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€687

Your trip at a glance

Start in Siena

You choose the pickup spot.

Montepulciano

Feel free to explore at your own pace and discover

Stop: 3 hours - admission not included

Montepulciano is renowned for its pork, cheese, "pici" pasta, lentils, and honey, but it's known worldwide for its wine. Connoisseurs consider its Vino Nobile among Italy's best. The city, full of elegant Renaissance palaces, ancient churches and hidden corners, boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it. It has one of the most intact and architecturally unified historic centres of any Italian town: within its walls, no major building work has taken place since 1580. Piazza Grande is the heart of Montepulciano and the setting for its main events, including the Bravio delle Botti barrel racing contest held in August every year and much more. Just be prepared to share the town: Montepulciano has received great attention following the filming of the vampire saga Twilight sequel New Moon here and has seen a notable increase in visitors.

Pienza

Feel free to explore at your own pace and discover

Stop: 2 hours - admission not included

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

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.

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

Comfortable and Safe Rides in Mexico

Used Daytrip for two rides in Mexico, which were both great. So comfortable, and we arrived at each of our destinations at a great time. Both were incredible drivers, and we felt so safe. One of our drivers, Miguel, also played the best music! Will definitely use Daytrip on our next trip to Mexico.

GolourdesduarteFebruary 20, 2025

Great way to travel and see some sights on the way

We did not know what to expect with this trip and booked from Australia. We were initially looking for an easy way to travel from Granada to Malaga. We decided not to waste the opportunity to see something additional on our way. Miguel certainly exceeded our expectations. His English was excellent (unfortunately we speak very little Spanish), and he was very friendly and helpful. We thoroughly enjoyed hearing about the regions as we passed through and also discussing some of the local ways. Miguel took us to Antequera as planned and ensured we were able to easily get our tickets to the attractions without any sense of rushing us. We were picked up and dropped off punctually and really enjoyed our trip. Hopefully we will return to Spain and we can use this service again sometime.

Michelle RFebruary 10, 2025

Excellent service

We used the service twice while in Thailand. Extremely prompt and efficient customer service. Best rate being offered in Chiang Mai for the travels. Polite, punctual, professional and English speaking drivers. Clean, comfortable vehicles. Being a regular visitor to Thailand, this was hands down the best service. Most pleased with the company. I hope it sustains the excellence of service that was rendered to us.

OmarJanuary 25, 2025

See more reviews

Siena to Montepulciano and 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.

Explore similar trips from Siena

Frequently Asked Questions

More Day Trips

More Day Trips