Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni | La Vacanza Travel

Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

Duration: 10 hours 30 minutes
Destination: Italy, Toscana, Florence
from
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  • 10 hours 30 minutes
  • Florence
  • E-Voucher
  • Lowest Price
  • Not-Cancellable

Overview

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.

Stop At: Florence, Florence, Tuscany

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.

Duration: 1 hour

Stop At: Monteriggioni, Monteriggioni, Tuscany

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.

Duration: 1 hour

Stop At: Siena, Siena, Tuscany

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.

Duration: 3 hours

Stop At: Piazza del Campo, 53100, Siena Italy

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.

Duration: 15 minutes

Stop At: Duomo di Siena, Piazza del Duomo 8, 53100, Siena Italy

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.

Duration: 15 minutes

Stop At: San Gimignano, San Gimignano, Tuscany

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!

Duration: 1 hour

Stop At: Piazza della Cisterna, Piazza Della Cisterna, San Gimignano Italy

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.

Duration: 30 minutes

Stop At: Gelateria Dondoli, Piazza Della Cisterna, 4, 53037 San Gimignano SI, Italy

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!

Duration: 5 minutes

Stop At: Florence, Florence, Tuscany

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.

Duration: 1 hour

Stop At: Chianti Road, Italy

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!

Duration: 2 hours

Sample Menu

• Cheese, bruschette and cold cuts
• Pasta with bolognese sauce or tomato sauce
• Typical Tuscan biscuits

Inclusions
  • Journey by fully-fitted GT Coach with Free Wifi on board
  • Expert multilingual Tour Leader
  • Siena tour with professional guide with Headsets (not included in the semi independent option)
  • Visit to a charming wine estate in the Chianti area with tasting of up to 2-3 Chianti wines
  • Sampling of wines, extra-virgin olive oil and regional products
  • Free time in San Gimignano and Monteriggioni Medieval towns

Exclusions
  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets (approx. 7€ pp)
  • Lunch
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • No heart problems or other serious medical conditions
  • Travelers should have a moderate physical fitness level
  • 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
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 63 travelers
  • Confirmation will be received at time of booking
Departure Point

Piazzale Montelungo, Firenze FI, Italy


Departure Time

08:45 AM


Return Details

Returns to original departure point

Voucher info

You can present either a paper or an electronic voucher for this activity.

Duration

10 hours 30 minutes


User's Reviews

Y6835TZdianew

19 Apr, 2024

You will visit 3 areas by bus with a bathroom stop before Siena. The driver and the tour guides were awesome. They are all multilingual and tailor the tour to make sure everyone is in included and understands. The bathroom stop was a very cool medieval castle. Wish we could have stayed a little longer as there was not enough time to explore the castle. Siena was a long stop and we took the 1-hour guided tour to begin. I would not recommend it. It was scratchy and I couldn’t hear 75% of the time. You are better off exploring on your own. Siena is a lunch stop. We chose Restaurante Al Mangia. DON’T go there! Food is so-so, prices are high and at the end they provide you with a $10 “cover charge” and we’re unable to explain what it “covered.” Stick with the restaurant the tour guides recommend. The next stop was wine tasting and it was the highlight of the trip. I live near Napa California so I expected a wine tasting with hundreds of people to be pretty lame, but I was wrong. It was awesome, very entertaining and fun. Hint: they give you food also so keep your lunch light. The wine tasting alone was worth the price of the tour. The 3rd stop is another Midieval town for some free time exploring. The town looked very interesting, but the weather turned cold and rainy so I didn’t see as much as I would like. (This is not the tour operators fault though.) The bus was comfy, but has no bathroom so plan accordingly. Bottom line: it was a nice tour and you absolutely get your money’s worth. Don’t forget to tip your hosts. It is a loooong day of work for them and they do an excellent job.

Barbara_T

17 Apr, 2024

The sights were absolutely amazing, the wine tour informative and entertaining. Lots more walking than I expected

Rodney_H

15 Apr, 2024

As a fan of Ezio Auditore & Assassin's Creed, this Tuscany tour was a real highlight of our Italy trip. We thoroughly enjoyed exploring the fortified cities of Monteriggioni, Sienna & San Gimignano. (Personally, I could have done without the vineyard wine-tasing.) It was such great value as we did not need a tour guide to explore the places on our own.

Alex_N

15 Apr, 2024

We informed the company via telephone we would be a little bit late, to see if they could wait for us because we were coming from another city. The attendant said she would try to reach out to the guide and see what they could do. We were late 15 minutes, despite all the efforts to make it on time. I understand it can be a problem with the schedule, but no one called us back to inform us it wouldn't be possible to wait. To make it even more frustrating, when we got to the stop where the bus departed, other companies were providing the same service, including another group that was exactly waiting for a couple who were late, trying to call them and waiting until they had some information. We met the group in Siena, as the attendant said on the phone it would be the first stop. It wasn't, it was the second stop, so we missed 1 city. Additionally, the bus broke down after the wine visit. We spent an extra 30 to 1 hour waiting for other buses to arrive, which made us lose half an hour in the last city visit, which would be short anyway. We don't have much to say about the guides though. They were nice during the whole trip. I would recommend going to this square and getting the tickets from other companies there. The place is close to the train station and it's called Piazzale Montelungo (Firenze).

mandyscott4

12 Apr, 2024

Friendly, knowledgeable tour guides. First stop Monteriggioni was far too short, a toilet stop, the guide described it as. Wine tasting was fun, siena was stunning as was San Gimignano. Seats need to be allocated at booking, I did not get to sit with my husband. Far too many people on the trip, this made it difficult to take things in and look around. You had to concentrate on who we were following. Shame as it is well worth doing but just felt too rushed. Due to the number of people , information was given in 3 languages. This meant that there was talking nearly all the time, not relaxing. Again, the guides and driver were good. 😊

User's Picture Gallery

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Nice Experience

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Would definitely recommend this tour and would take it again!

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Exceptional and beautiful Tuscany

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Our guide, Gabriel gave...

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Amazing Trip. Well worth the journey.

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The bus tour is a MUST! You cover so much ground this way!

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Interesting experience

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Beautiful way to see the medieval towns.

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Wonderful day in Tuscany 🇮🇹

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Good introduction to Tuscany

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Amazing Day Trip to Tuscany Region

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Couples Day trip to Tuscany

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Beauty and History

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Best Tuscany Tour

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Wonderful day

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Under the Tuscan Sun.

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Personalized tour of Siena, medieval towns, winery, lunch and more!

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Beautiful Italian history and landscape

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Worthy day trip and value worthy too.

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Great Experience. Fantastic sights and places. Should not be missed.

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Nice day trip to Tuscany region.

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Well planned and comfortable

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Sienna Medieval Majestic Magical

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Worth it

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