Day trip

San Gimignano & Siena: Small Group Wine Tour from Rome

San Gimignano & Siena: Small Group Wine Tour from Rome

Likely to sell out

From US$ 254.51 per person

Likely to sell out

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
Reserve now & pay later
Keep your travel plans flexible—book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures apply. 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

4.8 /5

based on 9 reviews

Review summary

  • Value for money
  • Safety
  • Service
  • Organization

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It was just the best way to explore a bit of Tuscany. Both my driver and your operator were fabulous and extremely knowledgeable about the Tuscan area and it’s highlights. If you are looking for an all inclusive, immersive experience then this is the tour for you. The lunch and wine tasting at the San Gimignano winery was excellent and a great way to experience a number of Tuscany’s famous grape varieties. All wines are available for purchase too at cellar door, discounted prices relative to their online retail prices. They also ship anywhere in the world. Highly recommend this tour as it is one of the best available. Cheers!

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July 14, 2022

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

Product ID: 34884