San Gimignano to Chianti Region: Private day trip hero image

Tripadvisor Travelers’ Choice 2024

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Save the memories for later

“Cannot think of enough positive things to say about my amazing driver Arsenie.”

Ashley SDecember 31, 2024

Cannot think of enough positive things to say about my amazing driver Arsenie.

based on 5,176 reviews

based on 991 reviews on

Why you'll love this day trip

Unveil Tuscany’s fortressed allure. Monteriggioni enchants with intact medieval walls, while Castellina in Chianti showcases the region’s winemaking traditions, charming alleys, and scenic vineyard vistas.

Your trip at a glance

5 h 18 min

Round trip

Private driver

Start in San Gimignano

You choose the pickup spot.

Monteriggioni

Feel free to explore at your own pace and discover

Stop: 1 h 30 min - admission not included

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.

Castellina in Chianti

Feel free to explore at your own pace and discover

Stop: 2 hours - 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

San Gimignano to Chianti Region: Private day trip

Select date and travelers

Total price for a group of 1-3 travelers

€633

San Gimignano to Chianti Region: Private day trip

From €211

per person

Curated by experts, loved by travelers

Every stop is handpicked by our expert travel curators, inspired by thousands of real experiences our travelers still cherish. So you get the day trip everyone wishes they’d taken.

Your trip begins where and when you choose

Discover local insights you won't find in guidebooks

Experience the freedom to explore at your own speed

Perfect for you, no matter how you travel

What to expect on your day trip

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
Guided tours or entry tickets to paid attractions in Monteriggioni and Castellina in Chianti should be purchased separately

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.
Guided tours or entry tickets to paid attractions should be purchased separately.

We know, plans can change. Good news is you can get a full refund if you cancel your trip 24 hours before departure.

We are proud to have our world-class customer service. They are available for you, whenever you need help, 24/7.

1+ million travelers like you. Moments they’ll never forget.

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

Excellent service for transfers in Thailand

I was unsure about this company but a few good reviews on Trip Advisor made me take the chance. I am so happy that we did. We needed a ride from Chiang Mai to Chiang Rai. Our driver Saksun was an excellent driver - it's not a long distance to drive (by Texas standards!) but the road is challenging and there are a lot of places where improvements to the road are being made. It took around 3 hours with a stop at a place with very clean bathrooms, very interesting hot springs and a place to get a snack and cold drinks. Saksun had a vehicle that was fantastic for this type of drive - a very comfortable ride indeed and was obviously well maintained and very clean. I highly recommend this company. I used to post on trip advisor as "lakekariba" but got out of the habit of doing so. This company was so easy to use and the result was so enjoyable that I felt that the company Daytrip and the driver Saksun had earned our trust and a glowing review. Gillian and Ted Pearsall Austin, Texas

lakekaribaDecember 4, 2024

Excellent option to get to Vienna to Budapest!

We used Daytrip to travel between Budapest and Vienna with a 2 hour stop for lunch in Bratislava. Our driver Zsombor arrived on time at our hotel in Budapest and was very friendly and informative throughout our trip. His vehicle was roomy and clean and he was kind enough to provide us with some bottled water for the trip. Our quick visit stop in Bratislava was very nice as well. He gave us plenty of time to explore the city and have lunch before meeting him again when it was time to head for Vienna. Daytrip provided us with a happy and trouble free transfer between Budapest and Vienna. Many thanks to your team and especially to your driver Zsombor!

pgh1125December 3, 2024

Great communication with an actual person! They will take you ANYWHERE, No pre-set routes to choose from!

Last minute plan change and Daytrip was our last resort so I chatted with them and had an immediate response from a real person, best situation ever. Never used Daytrip before but the reviews were incredible so we took the chance and booked a driver at like 11-12pm and by 7am the next morning when we woke, they found us a driver and the driver had already texed us making contact! Very impressed and will definitely use them again. We went from Dubrovnik, Croatia to Tivat, Montenegro.

James BNovember 9, 2024

Perfect Transport

Andreas did a great job picking us up from Pireaus Cruise Port and taking us to our rental in Spata. The three of us had been on a long cruise and had 9 pieces of luggage. He arrived in an appropriate vehicle and loaded and unloaded all of it. We are very happy with out decision to book with Daytrip.

LuckyTraveler01November 1, 2024

1+ million travelers like you. Moments they’ll never forget.

based on 5,176 reviews

based on 991 reviews on

Frequently Asked Questions

A few more things you might be curious about

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.

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.

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.

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.

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.

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.

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.