Day tripsCountriesItalySan GimignanoSan Gimignano to Siena and Monteriggioni: Private day trip

San Gimignano to Siena and Monteriggioni: Private day trip

1 / 4

Private ride with a local driver

7h 30m
Round trip
Private driver
Trusted by 1+ million happy travelers across 120 countries
4.9
Tripadvisor Travelers’ Choice 2024
Tripadvisor Travelers’ Choice 2024
4.9
5176
Reviews

About your trip

Leaving San Gimignano, the roads slip into vineyard-draped hills along the Chiantigiana—Tuscany’s “Liquid Gold” road. Pause at family-run cellars for a barrel-side sip, then roll into Siena, where Gothic towers rise above honeyed rooftops. After exploring its fierce contrade spirit, end in Monteriggioni, a perfect medieval crown perched above the Valdelsa Valley.
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 €272
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€816

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 Siena, you'll have the freedom to explore the historic Gothic towers of this hilltown before continuing to Monteriggioni, where you can admire the views of the region, 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 in Siena and Monteriggioni should be purchased separately unless specified otherwise
  • Meals, snacks, and gratuity are not included
From €272
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€816

Your trip at a glance

Your trip at a glance

Start in San Gimignano
You choose the pickup spot.
1
Siena
Feel free to explore at your own pace and discover
Stop: 3 h 30 min - admission not included
Siena
Siena
Siena
Siena
Siena
Siena
The medieval city of Siena is most famous for the Palio, a bareback horse race that has been held in the city square twice a year since the 16th century. Outside of the race, the city is an alluring mixture of medieval architecture and Tuscan tradition. The main square is dominated by the early 14th century Palazzo Pubblico and its soaring tower. This historic building still houses the city's municipal offices, and welcomes visitors to learn more about the town's history in the Civic Museum. If you're up for a rewarding challenge, you can climb the 500 steps to the top of the tower for wonderful views of Siena and its surroundings. Also in the square is Siena's stunning Gothic cathedral, which is one of the finest in the country with its painted facade and interior filled with beautiful Renaissance frescoes. Of course, being in Tuscany, it's also a great place to sip one some wine and sample the region's cuisine.
2
Monteriggioni
Feel free to explore at your own pace and discover
Stop: 2 hours - admission not included
Monteriggioni
Monteriggioni
Monteriggioni
Monteriggioni
Monteriggioni
Monteriggioni
Dominating a hilltop in the rich Tuscan lowlands, this walled city was built by the Sienese at the beginning of the 13th century to defend the Cassia Road, and the cities of the Val d’Elsa and Staggia. Today, the walls are still in almost their original condition, the only changes being when the towers were lowered in the 16th century, and in 1921, 3 of the towers were lowered to the same level as the walls. Today, visitors are still able to walk the walls, and a combined ticket includes access to the interactive Armoury museum. The Romea Gate opens up into the main Piazza di Roma, which was originally used as a large vegetable garden that provided food when the town came under siege. Facing the square is the Romanesque Church of Santa Maria Assunta, which is as old as the town itself.
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

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

5.0
5176 reviewson Tripadvisor
or
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.

Great transfer option.
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.

It was a fantastic trip.
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.

Best transport company anywhere
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

Excellent experience in traveling
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.

Reasonably Priced and Safe Transportation
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.

Daytrip never disappoints
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.

Great driver in Egypt
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.

Comfortable and Safe Rides in 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.

Great way to travel and see some sights on the way
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.

Excellent service
OmarJanuary 25, 2025

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Frequently Asked Questions

If you have any questions, here are the answers.
Day tripsCountriesItalySan GimignanoSan Gimignano to Siena and Monteriggioni: Private day trip

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