Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

based on 1178 reviews

Duration:10 hours 30 minutes (approx.)
Location: Florence, Tuscany

From $71.2

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A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

WHAT'S INCLUDED

WHAT TO EXPECT

1. Florence
There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.
2. Monteriggioni
You will have one hour of free time to explore Monteriggioni, Tuscany's hidden gem. This town is encompassed by its stunning, medieval walls. The town itself is so well preserved, you will feel as though you have travelled back in time to the Renaissance era... Explore the small cobblestone alleyways, take in the lovely views, and enjoy a cappuccino in the essence of historic Tuscany.
3. Siena
Next, you will head to a truly unique, medieval city in Tuscany - Siena! The drive will take about thirty minutes, and then your guide will lead you through the picturesque, ancient streets in the heart of the city until you reach Piazza del Campo. In the largest square of the city, you will meet a local and professional city guide for your included walking tour of Siena. For about an hour, the guide will share fascinating facts about this incredible city (which is listed as a UNESCO World Heritage Site), and you will visit some of the most famous points of interest. The end of the walking tour will lead you to the Siena Cathedral, where you can enter at your own expense to see the breathtaking decorations and unique architecture.
4. Piazza del Campo
Your walking tour will begin in Piazza del Campo, a fascinating, oval-shaped piazza in the center of Siena. Not only is this a popular spot for locals to meet up with friends and relax, but it is also home to a historic palio horse race! Every year, the different neighborhoods of Siena join for the epic and exciting horse race. Your guide will share plenty of local stories as you walk throughout the Piazza and see some of the famous monuments. Your professional guide will share information in a way which brings the history of the city to life, in a vivid, storytelling manner.
5. Duomo di Siena
Your walking tour ends in front of the iconic Duomo of Siena. This absolutely stunning piece of architecture is equally as beautiful inside as outside; if you would like to enter the cathedral, you will have some free time to do so (ticket is not included). If you prefer to explore the city in your free time after the walking tour, there will be some time for independent sightseeing.
6. San Gimignano
Your journey through Tuscany will continue to San Gimignano, known as the "town of towers," because of its fascinating medieval towers still perfectly intact. The drive will take about an hour, and you will see the stunning "medieval skyscrapers" from a distance as your bus pulls into the historic town. Your guide will lead you past an incredible panoramic viewpoint of the Tuscan hills, then through the ancient city doors. You will have an hour to independently explore the town - walk the picturesque alleyways, visit the Duomo, or climb the tallest tower!
7. Piazza della Cisterna
As you walk through the characteristic alleyways of San Gimignano, you will inevitably make your way to Piazza della Cisterna. This is the main square of the city, and where you can find the Cathedral, Duomo, and iconic medieval architecture! Grab a homemade gelato and enjoy the lovely views of this perfectly preserved city.
8.
During your free time in San Gimignano, don't miss the opportunity to stop by one of the most famous Gelato Shops in Italy, the award winner "Gelateria Dondoli"! Let yourself be enchanted by the flavours and colours of their delicious home made ice creams and recharge the batteries for the rest of the day!
9. Florence
End your journey through Tuscany with unforgettable views of the Tuscan hills as the sunsets. The drive will take about an hour, and you will arrive in Florence in early evening.
10. Chianti Road
After exploring these medieval Tuscan cities, you will undoubtedly be ready for some Tuscan wine! Meet back with your group, and head to a nearby wine estate in the countryside outside of San Gimignano. In about fifteen minutes, you will arrive at this characteristic wine estate, where you will be seated in a modern and beautiful tasting room built into the cellar. Enjoy the delicious wine produced at the estate: during the wine tasting, the wine producer will share the secrets of Chianti wine production with your group. At the end of the wine tasting, you will have the opportunity to purchase bottles as a high-quality souvenir of your incredible day in Tuscany!

ADDITIONAL INFO

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Infants are required to sit on an adult’s lap
• Specialized infant seats are available
• Not recommended for travelers with poor cardiovascular health
• Travelers should have at least a moderate level of physical fitness
• A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
• May be operated by a multi-lingual guide
• Please note that the given order of the visits may change
• Please inform us of any food intolerance or allergy in advance
• Kindly note that the Semi independent option does not include the professional guide in Siena
• LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
• HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax

CANCELLATION POLICY

Posted By : John_R
An excellent full day tour to Monteriggioni, Sienna & San Gimignano. Perhaps Sienna could be half hour shorter and SG half hour longer. We enjoyed the wine tasting and lunch at Tenuta Torciana. It would be useful to know that lunch was not included and to bring cash for it. Guide on the bus was happy and enthusiastic. The native Senese guide in Sienna was very informative. A memorable day. 😃👍
Rating : full ratings
Posted On : 2024-05-20 06:59:33

Posted By : Akira_H
Too many people in a group. We hardly followed the guid. Wine tasting was not impressed. It was a good experience to visit old cities.

Rating : full ratings
Posted On : 2024-05-19 16:22:45

Posted By : Nick_C
These are breathe taking places and a must see if in the Tuscany area. The medical buildings are well preserved and our guides Roberto and Tiziana had great knowledge of the area. A great day all round with a wine tasting stop in the middle.

Rating : full ratings
Posted On : 2024-05-19 02:28:21

Posted By : Nick220866
A beautiful part of Tuscany with plenty to see. You are transported back to medival times in these well preserved gems. Our tour team of Roberto, Tiziana and Raoul did an excellent job, with great knowledge of the area and getting us from place to place.
Rating : full ratings
Posted On : 2024-05-19 02:21:19

Posted By : marinacX2508KW
Thank you very much to the guides Jacopo and Gabriele and the driver Mario. They were all very nice, Jacopo delivered the tour in 3 languages perfectly. My personal favourite was San Gimignano, I wish we had more time there to explore it! The most gorgeous village, perfect to admire Tuscany and shop for local craftsmanship items.
Rating : full ratings
Posted On : 2024-05-18 16:10:25

Posted By : angela_o
The tour guide Jacob, Margarita and Mario the driver were Awesome!!!
Would recommend this tour to everyone. The wine tasting was the best and sooo much fun. Thank you !!
Rating : full ratings
Posted On : 2024-05-18 13:24:45

Posted By : Steve_G
Visited beautiful towns, and had a lot of fun at the wine tasting.
The bus was comfortable and although it's a long day, it's a very pleasant trip and great way to see Tuscany.
Rating : full ratings
Posted On : 2024-05-17 18:23:00

Posted By : Kallyn_R
We took the full day tour of Monteriggioni, Siena and San Gimignano with Jacob, Margarita and Mario and it was phenomenal! It’s a long day but totally worth it. We were a large group of over 70 people and while I did feel a little silly following our guide in Siena wearing headphones I found the tour to be very interesting and helpful information for understanding the city better. I’m so glad we didn’t skip Siena! Seeing a medieval city was so different and even further steeped in history. I wished we had more time in each of the cities but given how much we had to cover the timeline made sense. There is a decent amount of walking and some hills especially in Siena. I would personally skip the organized lunch and find your own food as there are lots of options and super cute ones on the hilly streets. San Gimignano was a surprising gem and I really enjoyed the view (paid unfortunately, 5€ each) from the top of the wall in Monteriggioni. Really great tour, would recommend!
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Posted On : 2024-05-17 13:38:05

Posted By : L5706JBhelenf
I can’t thank Roberto, Tiziana, and Raul enough for their wonderful tour of some of Tuscany’s finest highlights. We really appreciated the special care taken to ensure a smooth and secure passage to each destination. In particular, we enjoyed Roberto’s extensive historical and cultural knowledge which provided depth and clarity at each point on the tour. Our personal highlight was climbing the tower of San Gimignano. We would recommend this team to anyone who wants to relax and enjoy Tuscany!
Rating : full ratings
Posted On : 2024-05-17 07:29:54

Posted By : Diane L
This was such a wonderful tour and such a great value for the price. Raul, Roberto and Tiziana were fantastic. Siena was beautiful and the wine tasting stop was spectacular!
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Posted On : 2024-05-16 16:28:15