Day trip

San Gimignano & Siena: Small Group Wine Tour from Rome

Day trip

San Gimignano & Siena: Small Group Wine Tour from Rome

Likely to sell out

From US$ 266.86 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 for a full refund
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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 1 day
Check availability to see starting times.
Live tour guide
English, Spanish, Italian
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

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 15 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

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This was a fantastic day trip. Being in a small group made the trip even better. Teresa was a great tour guide and Giovani kept us safe on the road as our driver, both made us feel very relaxed and looked after. The meal and wine were both great and Sienna and San Gimignano were beautiful places to see.

March 24, 2023

By far one of the most amazing experiences on our trip throughout Europe. The guides and driver would always ensure we were enjoying our time in the towns and offered assistance with just about anything! The winery itself is amazing and there was more than enough wine for even the more experienced drinkers in our group. Book this if you are able to!

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March 24, 2023

What to say?? This easily had to be one of our favorite days of our entire trip. Antoinette was our guide with the help of Josh, and they were such a joy to be with. Each place we stopped at was absolutely beautiful. We go to explore so much and see multiple sides to Italy. We already had such a fun and full day of exploring before we even got to the wine tasting, but oh my gosh, that wine tasting!! Soooo much delicious food and wine. It was less a tasting and more an experience, and the staff at the vineyard were so warm and welcoming. Would absolutely recommend this tour!!!

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March 24, 2023

Product ID: 34884