Private Tour: Siena and San Gimignano Day Trip from Rome

5 (27)
Rome, IT
5 (27)
Rome, IT
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Embark on a captivating journey through medieval Tuscany with this private tour from Rome. Let your knowledgeable driver guide you through the charming streets of Siena and San Gimignano, as you explore the rich history and stunning architecture of these UNESCO-listed cities. Marvel at the Gothic cathedral of Siena Duomo and soak in the vibrant atmosphere of Piazza del Campo, where the thrilling horse race of Il Palio takes place. In San Gimignano, be transported back in time as you wander through the medieval towers and discover the artisan craft stores of Via San Giovanni. With hotel pickup and drop-off, a professional English-speaking driver, and a flexible itinerary, this tour offers a truly personalized experience. Don't miss the chance to uncover the secrets of Tuscany on this unforgettable adventure.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Admission Not Included
  • 11 hours
  • Suitable for 1-8 Participants
  • Private Tour
  • Guided Experience
  • Private guided tour in Tuscany
  • Explore medieval Siena with its Gothic cathedral
  • Experience the rich history of San Gimignano
  • Marvel at the beautiful towers of San Gimignano
  • Learn about UNESCO-listed attractions and fine architecture
  • Hotel pickup and drop-off
  • Professional informative english-speaking driver
  • Transport by air-conditioned sedan/minivan
  • Private vehicle for the day
  • Flexible itinerary
  • Gratuities
  • Food and drinks, unless specified
  • Walking tour guide inside the sites

Popular Hotels Closeby

More about this experience


Experience the enchanting beauty of Tuscany on a private tour to Siena and San Gimignano, departing from Rome. This exclusive day trip offers a unique opportunity to immerse yourself in the rich history and breathtaking architecture of these medieval towns. With a knowledgeable English-speaking driver as your guide, you'll uncover the secrets of Tuscany while enjoying the comfort of a private vehicle.

What to expect?

Prepare to be captivated by the allure of Siena and San Gimignano. In Siena, marvel at the magnificent Gothic cathedral of Siena Duomo and explore the vibrant Piazza del Campo, where the thrilling horse race of Il Palio takes place. Discover the fascinating history of this UNESCO-listed city as you wander through its charming streets. Next, venture to San Gimignano, often referred to as "Medieval Manhattan" due to its impressive towers. This picturesque town is known for its exquisite craftsmanship and world-renowned wine production. Stroll through the narrow streets of Via San Giovanni and admire the towering structures that once served as defensive outposts during ancient feuds.

Who is this for?

This private tour is perfect for travelers seeking an intimate and personalized experience of Tuscany. Whether you're a history enthusiast, an art lover, or a wine connoisseur, this excursion caters to a wide range of interests. From couples looking for a romantic getaway to families wanting to create lasting memories, this tour welcomes all who wish to explore the beauty of Siena and San Gimignano.

Why book this?

Embark on this private tour and unlock the hidden treasures of Tuscany. Unlike crowded group tours, this exclusive experience allows you to customize your itinerary and spend as much time as you desire at each site. With the expertise of your English-speaking driver, you'll gain valuable insights into the history, culture, and traditions of Siena and San Gimignano. Enjoy the convenience of hotel pickup and drop-off, and travel in comfort in your own private vehicle. This tour guarantees a truly immersive and memorable journey through the heart of Tuscany.

Good to know

During this tour, you'll have the opportunity to taste the renowned wines of the region and savor the flavors of authentic Tuscan cuisine. Please note that food and drinks are not included in the tour price unless specified. Additionally, a walking tour guide inside the sites is not included, allowing you the freedom to explore at your own pace.


Travelers who have embarked on this private tour have praised the exceptional knowledge and professionalism of their English-speaking drivers. They were delighted with the flexibility of the itinerary, which allowed them to fully immerse themselves in the beauty of Siena and San Gimignano. Visitors expressed their awe at the stunning architecture and historical significance of these medieval towns. Overall, the tour received rave reviews for its personalized approach and the unforgettable experiences it offered.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

DriverinRome Transportation & Tours

(Pass by)

Venture north from Rome to Tuscany on a privately guided day trip, and spend the day in San Gimignano and Siena. As your driver chauffeurs you around the cities, learn about medieval Tuscany and see UNESCO-listed attractions, fine architecture and much more.

Duomo di Siena

Our first stop this morning will be Siena, without doubt, one of Italy's most enchanting towns. Its medieval centre is full of majestic Gothic buildings such as Palazzo Pubblico in Piazza del Campo, Siena's main square. Twice a year the Sienese celebrate their rich medieval heritage with a horse race called the Palio, which attracts visitors and spectators from around the world. Spend a few hours exploring the town and perhaps the Duomo. The cathedral's green, pink and white marble exterior is surpassed only by the exquisite black and white marble geometric patterns and the inlaid marble mosaic floor found inside. This was the first European city to ban traffic from its main square in 1966. Sit down and, while sipping a cup of coffee, enjoy the stunning view.

Admission Not Included

San Gimignano 1300

You will then proceed to San Gimignano, Italy s Medieval Manhattan or the city of the belle torri (beautiful towers) rising imperiously above the vineyards of its own wine-growing area. Built as status symbols and defensive outposts, the towers played a significant role in the internecine feuds that eventually led to the town's downfall. Prior to its eventual decline into a sleepy backwater, the town prospered through its position along the main pilgrim route from Northern Europe to Rome. Today it is better known for its tourism, wine production and rich artwork. Piazza del Duomo is a good starting point from which to explore the historical buildings of the town. The Collegiate church, situated at the town's heart, is most famous for its frescoes of outstanding beauty, the greater part of which dating from the 14th century



5 (27)


Davide was our driver today. He was fantastico. Very full of historical and current local knowledge which he shared in a very entertaining way. Davide picked up our family of 8 this morning and made our day the most wonderful day we have experienced since arriving in Rome. His suggestions for photos, shopping, snacks and lunch in Tuscany were all great. Thank you so much. We highly recommend Davide and DriverinRome.


Fabio was a delightful driver which made for a fantastic day visiting beautiful Sienna and San Gimignano. I highly recommend this tour!


Most memorable time in Tuscany where we visited 1. San Gimignano 2. Monteriggiona z(Lunch) 3. Sienna A special call out to Matteo whom made everything possible and reservation at a wonderful restaurant in Monteriggiona Tuscany is now one of my favorite places in the world. If you are reading this review trust me don’t hesitate book your private tour to the Tuscany’s.

Rachel S

Fabio is an amazing driver and tour guide. He is very knowledgeable about the area of Tuscany and we truly appreciated his wisdom and kindness. We loved our day trip to Siena and to San Gimignano. The ride was picturesque and the towns themselves were incredible. We HIGHLY recommend this tour and especially FABIO!!!


Alexandra was a wonderful tour guide. Very accommodating and friendly. Great restaurant suggestion in Florence.


Matteo was very good, he told us about the places we wanted to see (Siena,Monteriggioni and San gimignano which were all beautiful and amazing to walk through. We had a wonderful lunch which Matteo arranged for us. Highly recommend - Grazie


We had a great visit to Assisi. Alex was our tour guide for the day. He was knowledgeable and very informative. He kept us safe and laughing. We saw spectacular areas of Italy. 5/5 recommend this tour and Alex.


Our driver Davide was absolutely wonderful! We had to switch hotels last minute and he was very accommodating in changing the pickup location at the last minute. He chatted with us as we drove through Tuscany and made sure to note any points of interest. We talked about Italian culture, language, and history. He was great! The vehicle was a Mercedes sedan as advertised and was very comfortable. We were able to leave town a bit early to beat traffic and crowds at the Duomo in Siena. If you only have minimal time to spend in Tuscany, you cannot miss the Duomo in Siena. It is unlike any cathedral we have every visited with an unbelievable amount of unique art! Make sure you peek inside the Piccolomini library for a view of some original illuminated manuscripts. Davide also made arrangements for us to spend the afternoon at a Tuscan winery for a tasting last minute as well! This was a wonderful day drip still getting us back to town for leisurely evening in Rome. Again, we cannot recommend Davide enough! He really went above and beyond and made our day wonderful!


Mateo was truly wonderful. He picked us up at the port in Rome on time (he was early) and whisked us away for our drive up to the Tuscany region. He provided us with a wonderful lesson in the history of the area as we travelled making the ride go by quickly. He was truly fantastic My wife and I promise to be back Bellissimo


Wonderful time exploring Sienna & San Gimangno. Alex was an excellent driver. He pointed out many areas of interest. DriverinRome kept us informed of times etc.
Collected by Evendo & our supplier partners
2024-07-15 20:02