Day trip

Florence: Siena, San Gimignano & Chianti Day Trip with Lunch

Florence: Siena, San Gimignano & Chianti Day Trip with Lunch

Likely to sell out

From US$ 124.99 per person

Likely to sell out

Enjoy a full–day experience of Tuscany's most breathtaking towns. See the highlights of Siena, the beautiful Tuscan wine country, taste genuine food and wine and stroll around San Gimignano.

About this activity

Free cancellation
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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. Learn more
Duration 9 hours
Check availability to see starting times.
Skip the ticket line
Live tour guide


  • Benefit from a small–group for an intimate experience
  • Explore the beautiful medieval city of Siena on a guided walking tour
  • Admire the famous Tuscan countryside
  • Enjoy a typical Tuscan lunch with traditional wines
  • Stroll through winding cobblestone streets in hilltop San Gimignano
Full description
Hop aboard your minibus at 7:45 AM and drive for around an hour through the Tuscan countryside. Enter the heart of Siena, and start the visit with your guide. Take off through the town's narrow streets and hear stories about Siena as you go. Skip the line to see the interior of the magnificent cathedral, and pass through the shell–shaped Piazza del Campo, where the Palio horse race is held twice a year. After your walking tour, enjoy some free time to enjoy Siena at your own leisure. Move on to San Gimignano, and admire the unique Tuscan landscape as you drive through marvelous scenery surrounded by olive trees, vines and old stone buildings on your way. Stop at a family owned wine estate to relax and enjoy a traditional Tuscan lunch for a taste of country hospitality. After lunch, take an easy drive to San Gimignano to finish your day. Famous for its splendid skyline of tall medieval towers, have free time to explore on your own. Discover the main street full of typical shops, have a look at the Collegiata (main church), or enjoy a gelato. Return to Florence in the late afternoon.
  • Small group personalized experience (maximum 25 people)
  • Professional and informative English–speaking driver and guide
  • Transportation by air–conditioned and fully equipped vehicle
  • Free Wi-Fi on board
  • Guided walking tour of Siena
  • Entrance fees to Siena Cathedral
  • Delicious lunch at a winery with wine tasting
  • Hotel pickup and drop-off
  • Tips
Not suitable for
  • People with mobility impairments
  • Wheelchair users
Covid-19 precautions

You must book this activity online because the ticket office is closed

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



Meeting point

• Meet at Piazzale Montelungo, at the bottom of the highest red-brick building, opposite the parking lot (approximately 8 minutes walk from the Florence SMN train station). • Your guide will be holding a sign with "Tuscan Gems" on it. • Please note: if you use Google Maps, do not follow the itinerary passing through the train station. The exit there is closed. • Check-in will be at 7.45 am.

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Important information

What to bring

  • Passport or ID card

Know before you go

  • Vegetarian menu can be catered for, upon request at time of booking
  • Tour is in English only
  • The Siena Cathedral is not accessible on Sundays or during religious celebrations
  • Sample menu: assorted cold cuts, cured ham, salami, cheeses, bruschetta, pasta, or soup, salad, dessert and coffee, accompanied by the winery's own wines, olive oil and Vin Santo (sweet dessert wine)
  • Operates rain or shine – please dress appropriately
Customer reviews

Overall rating

4.9 /5

based on 27 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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After a lot of research booked this day trip. The day was wonderful from start to finish. Lorenzo from Prestige Rent was the perfect guide. Paid a bit extra to go in a smaller group in a mini bus rather than a big group in a coach. This was definitely the right choice. There were 18 of us in the group which was perfect as during the excursion got to chat to the others in the group making the day more fun and memorable. Siena and San Gimignano were both beautiful places to visit. Was nice to leave Florence for the day and see the beauty of the Tuscan countryside in a perfect day trip. Lorenzo guided us through both places with just the right amount of info making the day interesting and not boring like some guides can! The highlight of the day was the Chianti wine tasting … the family run vineyard was amazing. Lunch there was great … nice food accompanied by amazing wine tasting. Had an excellent memorable day.

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June 4, 2022

This tour was well run and made the perfect stops with the perfect amount of time at each stop. Stefano, our driver, and Alessandro, our tour guide, we’re amazing and so patient. Especially because we were traveling with 4 small children. The tour bus was super clean and fairly new (with air conditioning, a must in the Summer!). I highly recommend this tour if you want a taste of Tuscany and only have a day. Also, it was very family friendly.

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June 28, 2021

This tour was a perfect introduction to Tuscany. Our tour guide, Ellie, was very knowledgeable and gave us great recommendations for Siena and San Gimignano. We saw many churches while we were in Italy, but the Siena Cathedral may have been the most impressive. The wine estate was charming. Lunch was tasty and we now have a better understanding of Chianti wines. We appreciated the smaller size of the group.

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October 30, 2019

Product ID: 130077