Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

based on 1213 reviews

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

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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 : U2305UFstevem
We had a great time on the Medieval Gems of Tuscany tour, led by Roberto who kindly and deftly navigated our tour--leading in both English and Spanish. The trip covered some beautiful places, Roberto made sure everyone had what they needed and gave great insight as to the history and unique character of these places. Our three generations of family (with ages ranging from 7-69) all enjoyed the day. We took the guided tour in Siena--which was quality and the perfect length. The winery we stopped at was fun--I'm a wine snob and found the quality of wine superior.
The only thing that I wish was that we had maybe another hour at Siena and San Gimignano--but maybe it's just motivation to go back!
Rating : full ratings
Posted On : 2024-06-10 15:32:22

Posted By : Joseph_C
The tour brought us to 3 areas in Tuscany. However, I booked a classic ENGLISH TOUR and instead the tour was bilingual. There was no mention of this when I booked. Thankfully , the groups were separated for the expert tour of Siena. The tour was also too crowded.
Rating : full ratings
Posted On : 2024-06-10 13:19:21

Posted By : Soroosh D
Amazing tour which was well organised. Free time available in each stop for exploration, photos, food, and Gelato. Our hosts Sebastian and Elaria were great. As we did our tour on a Sunday, we were lucky to encounter the "Festival of Districts" in Siena, with the Blue and Yellow district in full Parade. Truly marvelous, couldn't have planned that timed that better if I tried. Brought the old medieval district to life. The English and Spanish groups travel together, but separate on the guided tour and the wine tasting. Met lots of cool people, with great conversation. Best way to see Tuscany in 1 day (avoiding the Pisa stop meant there was more time per stop here).
Rating : full ratings
Posted On : 2024-06-09 18:33:14

Posted By : Tracey_C
Our tour with Sebastian, Mario and Elaria was fantastic. They gave us a nice mix of providing us with some history while also giving plenty of free time to spread our wings.
Rating : full ratings
Posted On : 2024-06-09 16:39:01

Posted By : stefanfI582IH
Smart option we choose. Beautiful tour, well organized, with good balance between "on the road" and visiting places. Good food...good wine tasting, with lovely presentation.
Very beautiful places with astonishing views. And a lot, a lot of amaizing history.
But all these would have not been the same without our guide, Sara!
She provided so much information in such a nice and friendly way.... also she took very care of us....we felt safe...but more, we felt her personal involvement, beside profesional one.
Thank you Sara! Thank you "CiaoFlorence"!
Marilena and Stefan
Rating : full ratings
Posted On : 2024-06-07 03:36:58

Posted By : U9837VLrachelb
What a wonderful way to spend your day! It’s a long day but if you want to learn the history of the Tuscan people and their culture it’s worth every minute. I couldn’t be happier with how the day went! Sara our tour guide was amazing. She was extremely thoughtful and considerate of everyone on the trip and gave great information on our drives to and from places. You also get a reasonable amount of time at each stop to do some shopping or sightseeing which i really appreciated. All in all it was a 10/10!
Rating : full ratings
Posted On : 2024-06-06 14:33:42

Posted By : H7486FMmichelep
Sara was a very friendly, kind, and helpful guide. This tour was a great and easy way to see more of Tuscany in a day without having to worry about getting around. My friend and I had a lot of fun.
Rating : full ratings
Posted On : 2024-06-06 13:30:46

Posted By : Hunter R
Great way to see more of Tuscany away from the noise and bustle of Florence. Beautiful stops with time to shop and a lovely wine tasting at a true Tuscan vineyard!
Rating : full ratings
Posted On : 2024-06-06 12:19:08

Posted By : Vicki G
I was impressed with the slick organisation of this day trip. Our guide Roberto did an excellent job of keeping 50+ people informed, ensuring everything was clear and went smoothly and he did this in two languages. Impressive. It was a fun day with entertaining tour guide in sienna and an hilarious wine tasting in chianti. Also a big thank you to Luigi for his safe and careful driving. Overall a great day out and excellent value for money.
Rating : full ratings
Posted On : 2024-06-06 03:50:51

Posted By : Terri_F
Fantastic day! Great way to see Tuscany if having a short stay. Good value for money. Roberta was excellent as a host. Luigi a great driver.
Rating : full ratings
Posted On : 2024-06-02 12:42:08