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Tuscany Countryside including Wine Tasting & Lunch – Private Day Trip from Rome

Pickup and Drop off at Your Hotel


11 hours

Tour Type

Daily Tour

Group Size

8 people




Memorable Day Trip to San Gimignano and Siena

Escape the bustle of Rome for the day with this private driving tour through Tuscany. Take in Chianti’s rolling vineyards during the drive and visit the medieval towns of Siena and San Gimignano. Enjoy free time to admire Siena’s Piazza del Campo and Duomo before continuing on to a winery to taste some local wine and have lunch (included in the price). End your day with a stroll through the UNESCO-listed old town of San Gimignano.

  • Stress-free driving tour to Tuscany, with stops in Siena and San Gimignano
  • Free time in each town to sightsee and shop at your own pace
  • Sample classic Tuscan specialties and local wines at a countryside cellar
  • A private tour for more personalized attention and a flexible itinerary

How We Planned Your Trip from Rome to San Gimignano?

Your private day trip to San Gimignano and Siena will start when our expert driver/guide pick you from your hotel residence. While traveling through Tuscany in our deluxe air-conditioned van, the driver will start introducing you to your first stop.

It is because we want you to enjoy the complete panorama view of our first destination while keeping in mind the minute details about it. You can sit or walk there for a couple of hours to breathe in the fresh air of the narrow alleys of Medieval town

Moreover, you can have a look at Piazza del Campo, where the famous and traditional horse race of Siena (il Palio) is held twice a year, or climb over the Torre Del Mangia for an amazing view from the top.

A short drive through from there will take us to the best wineries of this region. Here, Luigi will give you a warm welcome, lunch along with a tasting of some wine from his family winery.

A long and enjoyable Rome to Siena day trip will end at the UNESCO world heritage, San Gimignano. It is a popular hidden gem of Italy that nobody would ever want to miss, offering a beautiful view of the skyline that’s truly breathtaking.

Plan Your Tour at Your Convenience!

Since it is a private tour, so you can plan the route according to your wish. You can stay at a place a little longer if you want to, or you can skip a destination if you like to prolong your visit to any specific destination. Our expert driver is there to give you suggestions about the insights of San Gimignano and Siena and what places you shouldn’t be skipping out.

Get the Best Packages for Rome to Tuscany Day Trip!

We are offering the best Italy tour packages depending on the number of passengers traveling along, at the most reasonable prices.

Our packages include:

  • 1-2 passengers: 630 euros.
  • 3-4 passengers: 660 euros.
  • 5-6 passengers: 690 euros.
  • 7-8 passengers: 740 euros.

If you have a group of more than 8 people, inform us beforehand to manage your trip accordingly.

Is San Gimignano Worth Visiting?

If you are a history lover and want to taste great wines, there’s no other place to visit than San Gimignano. The town is well-known for its historical aspects and the best visiting area for the people who search for ancient architecture and the wonderful countryside of Tuscany.

Till the fourteenth century, San Gimignano enjoyed the political and economic glory that can still be felt in the form of historical buildings and monuments. The city is built on the landscape of Tuscany, which gives a beautiful scenic view. And if you could take a walk from city walls, you cannot overlook the attraction of panorama Valle Elsa.

The most attraction for the Gourmet travelers is the perfect tasting of  DOC wines Vernaccia, Vin Santo, and San Rosso, whose grapes are directly collected from the hundreds of Tuscan vineyards.

Don’t Forget to Visit these Sights at Siena!

Another favorite pick of tourists is Siena, a city of Tuscany.

Here, you can see the famous Palio de Siena horse race. It is known as one of the oldest prevailing cultural traditions of Italy. It was first held in the 16th century, and from then, it became a part of their culture.

If you are fond of medieval architecture, then Siena is worth visiting. Due to multiple ancient buildings, it has become the UNESCO world heritage site as it has preserved the best architecture so beautifully. The place is not only accompanied by buildings, churches, and museums; it also has several stunning and mesmerizing places to stay as well.

The wide range of residences with Duomo views to the city walls will polish your stay in Italy. You won’t experience the standard hotel residences; you will experience the classic Italian hotels.

Cold feet? Book risk-free with free cancellations up to 48 hours before the service starts.

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  • Since it is a private tour so the itinerary is flexible and you can change it as you want, your driver will always give you the right suggestions according to your preference.
  • Due to strict Italian laws & regulations that protect officially licensed guides, our drivers can only comment and explain the sights from inside the vehicle, and are not allowed to do so once they are outside the vehicle. A Professional licensed guide, where needed, can be hired on request at an extra cost.


  • Pick up & drop off From your hotel
  • English speaking driver
  • Private transportation in first class air conditioned van
  • Tasting of 7 different wines, olive oil and balsamic vinegar
  • 4-course typical Tuscan lunch
  • An amuzing visit to beautiful sights of Siena and San Gimignano
  • Complimentary mineral water
  • Local tour guide.
  • Entry tickets to churches or landmarks.
  • Gratuities.

Tour's Location

Pickup and Drop off at Your Hotel


Based on 5 reviews
Very Good
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Georgina A.


Best Experience

Amazing immersion in the Italian history, art and cuisine. Perfect combination of sight seeing in 2 "must see" places in Tuscany, complete taste of the incredible food and wine from Tuscany and enjoyable and entertaining guide with Alan.
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Yuri - Germany


Wonderful day - highly recommend

This was an excellent tour. It was a long day, but it was full with lots of awesome sites and activities. Our driver/guide Sami was very nice and shared many interesting details throughout the day. I especially enjoyed Siena where Sami arranged a local tour guide to share interesting facts about the city. If you have a spare day in Rome, I highly recommend this tour!
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Mario - Australia


Great Tour!

Great tour in a very comfortable vehicle with a lovely guide! They picked us up on time from our hotel in Rome. The driver/guide was very friendly and professional and gave us lots of information during the way. All the places we visited were pretty amazing. Toscana is a beautiful area with lots of interesting places. We highly recommend the tour and the tour company!
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Tuscany in Comfort!

Awesome day with an awesome driver and tour guide! He took us to some beautiful places, great photo ops and even booked us a wine-tasting lunch! The only way to travel - in comfort and with someone who knows what they are doing! Ask for Sammi!!!
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Amazing day trip

The tour was really great. The Tuscan medieval towns that we visited (Siena & San Gimignano) were so beautiful full of history and stunning views of the countryside, food was delicious and our driver Assem was fantastic and very friendly. Certainly would recommend this private tour to anyone wishing to take just a day to enjoy Tuscany in his peace and very relaxed.
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