Day trip

San Gimignano & Siena: Small Group Wine Tour from Rome

4.7 / 5

7 reviews

San Gimignano & Siena: Small Group Wine Tour from Rome

Likely to sell out
Likely to sell out

From US$ 262.03 per person

Spend a day exploring medieval towns in Italy on a journey from Rome to San Gimignano, Monteriggioni, and Siena. Visit 2 UNESCO World Heritage Sites, taste the local Chianti and Vernaccia wines, and absorb the history and culture of these unique towns.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
Reserve now & pay later
Reserve now & pay later to book your spot without any charges today. Learn more
Duration 1 day
Check availability to see starting times.
Live tour guide
Italian, English, Spanish
Pickup included
Pickup is available from accommodations within Rome city center only (inside the Aurelian Walls).
Small group
Limited to 12 participants


  • Visit the Tuscan towns of San Gimignano and Siena
  • Travel in comfort in an air-conditioned van with a maximum of 6 participants
  • Taste food and 10 different types of wine tasting at local wineries
  • Benefit from your tour assistant who will travel with you throughout the tour
Full description
Travel through Italy on a full-day journey from Rome, through the hills of Chianti, to the cities of San Gimignano and Siena. Arriving in San Gimignano, a UNESCO World Heritage Site, explore its charming medieval streets and sample the world-famous Vernaccia white wine. Stop for a wine tasting and sample local products in a beautiful wine cellar: 10 different types of wine and oil. Then visit the estate and learn about the processing of the grapes before having lunch at a restauarant.  Finally, make your way to Siena for a lovely wander around the historic center of the city, a well-deserved UNESCO World Heritage Site. Walk along Piazza del Campo, the public square that's also home to the Palio di Siena horse race. Visit the Mangia Tower, and admire the Duomo's Romanesque-Gothic facade, before beginning the trip back to Rome through the Tuscan countryside.
  • Transport by air-conditioned minivan (no more than 6 people)
  • Tour escort for the whole trip
  • Tasting of local wine
  • Light lunch of local food and wine
  • Pick-up and drop off (inside the Aurelian Walls)
  • Gratuities
  • Local guide
Not suitable for
  • People with pre-existing medical conditions
  • Wheelchair users
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

Select participants and date



Important information

What to bring

  • Comfortable shoes
  • Sunglasses
  • Camera

Not allowed

  • Luggage or large bags

Know before you go

  • The tour goes on rain or shine
  • No refunds for missed flights, buses, trains, etc.
  • There is a total refund for cancellations made within 72 hours of the tour's departure
  • It is recommended that you wear comfortable shoes, and remember that is not permitted to visit churches in shorts or miniskirts, or with uncovered shoulders
Customer reviews

Overall rating

4.7 /5

based on 7 reviews

Review summary

  • Value for money
  • Safety
  • Service
  • Organization

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Giuseppe "Pino" was a great tour leader--very friendly and knowledgeable. He was quick to point out sights and fun facts on the road and was always willing and able to answer any questions I had. I wish I had been prepared with more questions, though, like why the two sights have UNESCO status. Massimo was a great driver. This was a good tour but it was one of the more costly tours I've seen online that are not characterized as luxury. At the same time, it was essentially a private tour but not charged as private. I booked it because another, similar tour I wanted was canceled for lack of participants and I really wanted to see these two towns. Unless you absolutely need to tour from Rome, you might try a tour that proceeds from Florence instead.

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May 18, 2022

Both cities are worth visiting, they are very beautiful and picturesque from the Middle Ages. We are not wine fans, but the tasting was good and the food abundant. Perhaps I would give more time to get to know Siena well. Very professional and proactive driver, always helping with a smile, but the guide is a lady who knows half Spanish and was not entertaining, it was a drag because we had her on 3 tours and she was very boring.

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December 5, 2021

Adam (our driver) and Fabio (our guide) were a perfect pair. Fabio was very knowledgeable and quick to answer questions and recommend shopping and eateries, They both kept us on schedule and made sure that we saw all that we could see during our day. Fabio had great relationships in the areas that we visited and was able to provide great service. When asking about another excursion that we were planning ourselves, both Adam and Fabio were quick to offer options and solve our problems on how were were going to get to Pompeii and the Amalfi coast on our 2 day plan. They went out of there way to arrange for us to join their planned tour to Pompeii and the Amalfi Coast along with dropping us at our hotel for our extended stay. In addition to that, Adam met us the next evening to bring us back to Rome. We were thrilled with all they planned for us for both Siena & San Giminiano along with our trip to Amalfi.

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September 21, 2021

Product ID: 34884