10 Historical & Heritage Tours in Monteriggioni That You Shouldn't Miss

January 29, 2022 Jacquiline Delozier

Monteriggioni is a comune in the province of Siena in the Italian region Tuscany. It borders on the communes of Casole d'Elsa, Castellina in Chianti, Castelnuovo Berardenga, Colle di Val d'Elsa, Poggibonsi, Siena and Sovicille. The town is architecturally and culturally significant; it hosts several piazzas, and is referenced in Dante Alighieri's Divine Comedy.
Restaurants in Monteriggioni

1. Florence Private Day Trip to Siena and San Gimignano

LuccaLimo
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5.0 based on 1 reviews

A customized day trip of Siena and San Gimignano for the discerning traveller seeking an authentic Italian experience on a small group tour with only the very best of English speaking driver-guides.  Travel from the centre of Florence to discover the one-time capital of Tuscany, Siena and the enchanting hilltop towered town of San Gimignano.  Visit Italy close up in a Mercedes minivan of up to 7 - 8 people that takes you into the very heart of each of these beautiful Tuscan cities.

Inclusions: Bottled water, Driver/guide, Florence hotel pickup and drop-off, Transport by private vehicle

Exclusions: Museum & Monument entrance fees, Lunch, Gratuities

Reviewed By Psinclair12

Super responsive, caring, thoughtful service that I worked with on my most recent Italian vacation. From the first email to the last drop off, they were simply the best. A pick up at the very hard to navigate Florence train station--flawlessly executed. An amazing restaurant recommendation on the trip from Florence to Lucca. Courteous, professional, communicative from Florence to Lucca, to La Spezia, to Lucca, to Pisa. Wonderful!

2. Private Minivan Tour to Siena and San Gimignano from Florence

Piazza dei Cavalleggeri, 50122 Firenze FI, Italy ACCORD Italy Smart Tours & Experiences
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5.0 based on 2 reviews

During this private open-air tour in a comfortable minivan, you will explore the breathtaking towns of Siena, Monteriggioni, and San Gimignano. All are symbols of Medieval and Gothic architecture, characteristic elements are the historic towers, pointed arches, and narrow streets. Moreover this Tuscan area is full of superb food specialties you will surely have the chance to taste, such as Panforte and Pici. The tour lasts 8 hours with 2 hours spent in Siena, a short visit in Monteriggioni for a photo stop, and approximately 1 hour in San Gimignano.You will also get a detailed description from our expert local guide in Siena.

Inclusions: Professional local guide in Siena - 1 hour, Air-conditioned minivan, Hotel pickup and drop-off from central hotels, Light lunch in a restaurant or farmhouse (depending on availability)

Exclusions: Guide in San Gimignano (upon request), Food and drinks, unless specified

Reviewed By sandyc17

My husband and I did this tour and it was fabulous - the driver was great and there were only four of us so you could talk away to the driver - we scooted through the city easily on the golf cart and it was such good fun and we saw loads of amazing stuff, I’d highly recommend this tour

3. Full day wine tour from Florence: Chianti and Badia a Passignano

Via Elio Gabbuggiani, 7, 50144 Firenze FI, Italy My Tour in Italy
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5.0 based on 5 reviews

Spend your day in the Countryside surrounded by Chianti hills and enjoy the view that only this place can offer while tasting and drinking incredible wines and local products. Forget the touristy places and live this authentic experience; your visit to Tuscany would not be complete if you did not experience a traditional wine tasting and meal in the great Chianti area.

Inclusions: Travel by GT coach or minivan, Expert tour guide, 2 wine tastings in 2 Chianti wineries, Typical Tuscan lunch with barbecued meat and vegetables, Visit Badia a Passignano

Exclusions: Gratuities, Pickup and dropoff

Reviewed By Oversunsetplain

I couldn’t put correct date on this review - I did this tour with my two children in August 2019 and originally posted it then. I have had a message to say that I had posted it under the wrong company (one with a very similar name). I would like to re-post the review as we had such a brilliant day with our guide and would like to recommend the tour company to others whenever this type of activity goes ahead again! Our guide Ms Ivanova was very knowledgeable and friendly. The tour took in many places around the city and we also visited the Uffizi in the afternoon. I was with my children aged 6 and 9 and both really enjoyed this day. They felt included and learned a lot. The guide met us at the times planned and gave plenty of opportunities for questions and were able to answer any queries. Everything was organised well and went smoothly. We were unable to book a tour inside the Duomo but actually this one which took us all the way around the outside and to other fascinating parts of the city was perfect for my family.

4. PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

UniqueTuscany private Tours
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5.0 based on 27 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • With this fascinating tour you will discover a unique part of Tuscany in a private day-trip from Florence. With an expert local driver/guide, immerse yourself in the renowned Chianti wine region and explore the cities of Siena and San Gimignano. You will tour historic landmarks such as Piazza del Campo in Siena, home to the annual Palio, and the medieval towers of San Gimignano. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the wine cellars by your guide • Taste Craft Chianti Classico wine at a local vineyard • Pick-up and drop-off at your Hotel or at the address provided • Travel in a Mercedes-Benz minivan

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes-Benz MiniVan, Air-Conditioned, English-speaking licensed driver, Free time in Siena and San Gimignano, Unlimited cold mineral water , On-Board WiFi

Exclusions: Local guides in Siena and San Gimignano, Lunch in farm or winery available at an extra cost 25€pp to 50€pp, depending on option chosen, Entrance fees (Cathedral of Siena ia approx. 7€ pp.)

Reviewed By Gabriel S

This was our 2nd private tour that we did through Uniquetuscany (2017/2020). Our guide, Alessandro was very specific to the covid restrictions and offered us new masks during the day! He did a wonderful job explaining the history of the towns. Our highlight was the visit to Tuscany organic farm where we had our lunch with amazing view. We stopped at Siena, San Gimignano and Pisa. There was a lot of walking and moving from in and out of the minivan so make sure you wear comfortable shoes. I definitely recommend this tour while visiting Florence since you get a lot of history while on the minivan to each town. Just not enough time in all the towns but 10 hours is a long day! still worth the trip! Highly recommended..

5. Semi Private Small Group Best of Chianti Landscapes and Wine Tour from Florence

Via della Scala, 57, 50123 Firenze FI, Italy I Just Drive
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4.9 based on 59 reviews

Chianti wine tour and landscapes. Enjoy an unforgettable day trip in the Chianti Region.Your tour features stops in Monteriggioni, San Gimignano and Siena followed by a visit to a winery with wine tour, wine and olive oil tasting, also pecorino, salami, and prosciutto tastings. You  will venture for a Full Day semi-private Excursion into the Tuscan Countryside. Meander down the Chianti highway with your local English speaking driver, enjoying the vineyard laced hills and the endless olive tree. Your driver, a Tuscan local, can help you pick out the best spot for a truly typical meal.  This is a wonderful opportunity to explore the region outside the city, and to really see how special Tuscany is. Shared small group tour.

Inclusions: Bottled water, Wine tasting and olive oil tasting, Snacks, Pickup and drop-off from designated meeting points, Small-group tour max 8 people in a Mercedes Van, Hotel pickup and drop off for centrally located Florence hotels only

Exclusions: Lunch

Reviewed By nwagenbr1

We had the best day with our driver Daniel for the "Chianti Best" tour. I would recommend this to everybody. Our driver was super knowledgable and friendly and made seeing all these beautiful places so convenient and fun with so much great background information. I would book the "I Just Drive" service for any tour. Financially you get so much for your money - Highly, highly advise.

6. Small-Group San Gimignano and Volterra Day Trip from Siena

Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Tuscan Escapes
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4.9 based on 48 reviews

Embrace the medieval charms of Tuscany's towns on a full-day trip to San Gimignano and Volterra from Siena. With an attentive local guide, walk round the Fortress of Monteriggioni, explore the UNESCO World Heritage-listed town of San Gimignano, and visit an alabaster workshop in Volterra. Enjoy a delicious lunch on a small Tuscan farm and spend time at your leisure exploring these rustic hill towns that are steeped in rich Italian history. Numbers are limited to eight people on this small-group tour, ensuring you'll receive personalized attention from your guide.

Inclusions: Driver/guide, Lunch, Transport by air-conditioned minivan, Visit to alabaster workshop

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By Pioggiola

We did a 3-hour private tour of Siena with Giorgia this summer with our two teenage children. It was just perfect! Giorgia is extremely knowledgeable about all aspects of Siena and beyond, and it clearly showed in the depth of her answers to the very many questions that we asked. She was flexible to adapt the tour based on what we were interested in. Although not originally from Siena, she knows and loves the city like a local and has the ability to make the tour unforgettable. 160 Euros for a fantastic private our of Sienna. Very good value for money. Probably the best private city tour that we have ever done.

7. Private Excursion to Siena, San Gimignano and Chianti Landscapes

Caf Tour & Travel
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4.8 based on 22 reviews

Discover the beauty of Siena and San Gimignano, traveling through the countryside of the Chianti region, with ever changing scenery of vineyards and olive trees on this full day private trip from Florence.

Inclusions: Pick up and drop off at your Hotel if centrally located in Florence, Transport by deluxe air-conditioned vehicle with WIFI on board, English/Italian speaking driver, Local professional Guide at your side in Siena

Exclusions: Gratuities, Guide Service in San Gimignano, Entrance fees to the Cathedral in Siena, Everything not mentioned as Included

Reviewed By aakebe

Only 7 people and the tour was by Van. The driver guided us during the drive but no guide joined us at our stop in Castellina. Professional presentations at the wineries. Especially at Poggio Amorreli with Andrea where we were treated with Spumante, one white and two red Chianti and one supertuscan. We also got bread, cheese, salami with their own balsamic vinegar and olive oil. The driver called for a taxi upon arrival in Florence ????

8. Best of Tuscany Hill Towns semi-private full day tour (Siena & San Gimignano)

Piazza della Repubblica, 50123 Firenze FI, Italy Avventure Bellissime
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4.7 based on 53 reviews

Our tours offer you a more personalised and in-depth experience. This tour of Siena, San Gimignano and Monteriggioni starts at 8am and runs until 5pm in the evening. You will have all the time you need to experience the beauty of the countryside. Since you are in a small group, our very experienced English speaking driver - escorts have far more time to interact with you and answer any questions you may have.

Inclusions: Min 2 people for guaranteed departures / Max 6-7 people, A/C Mercedes vehicle or similar make (max 7 people), Local Expert English Speaking Driver-Escort, Visit Siena, San Gimignano and Monteriggioni Hill Towns

Exclusions: Gratuities, Hotel pickup and drop off, Food and drinks, unless specified

Reviewed By 126albertd

For our honeymoon in July 2017, we purchased the "Semi-Private 12-Day Magic of Italy Vacation Package" that let us savor the best of Italy, including the history and art of the big three (Rome/Vatican City, Florence & Venice), while combining that with two-night stays in Sorrento on the stunning Amalfi Coast and in the classic Tuscan hill town of Siena. In addition to that, we selected stop-overs in Pompeii (Day 4), a private half-day Brunello tour where we got to visit, drink and eat at the famous Montalcino winery (Day 7), a private half-day tour to Pisa where we climbed to the top of the Leaning Tower (Day 8). We also did some unscripted side trips -- first to Naples and later to Burano. All in all, we got to get a very nice and casual taste of Italia, which was equal parts activities/sight-seeing/touring and shopping/leisure/resting. The people who helped put our trip together understood that we'd be strapped for cash after paying for our wedding, so they were very good about working within our budget. Usually to get to see that much of Italy in the summer time, it'd easily be more than $12,000, but we did this entire trip for about half that amount -- and I'm so thankful to them for making that happen for us! Additionally, I guess they informed everybody that it was our honeymoon, because every time we arrived at a new hotel, there was either a bottle of champagne, a fruit bowl or a letter congratulating us on our marriage, which was so very cool and unexpected of them. What happened with us is that once we settled on a price and signed our contract, a week before we were set to fly out to Rome, they e-mailed us all the vouchers. On each voucher, it said a time and place to meet up with our driver/tour guide (usually right in our hotel lobby or near the activity that we'd be doing that day), and almost as if like clockwork, we'd go down at the time they said with our voucher in hand, and the driver/tour guide would be standing right there holding a sign with our names on it. Every time they picked us up, if they were driving us, they'd show up in these black luxury Mercedes-Benz SUVs, and they would literally know the history of everything we passed, telling us all of it as we drove to keep us entertained throughout the rides. We'd ask them random questions, and they seemingly knew the answers to all of them -- it was rather impressive. Though they all spoke English perfectly, I did my best to speak to them in Italian, if only to practice what I'd learned in school years before, and 95% of the time, they understood me well enough. When they didn't, I'd fall back on English or Spanish and that would clear it right up. Nevertheless, they were always so kind to my wife and I. One driver even went so far as to personally call a great restaurant in Sorrento and set it all up for us so that we could have what seemed like a 7-course meal essentially for free (even though I did leave about a 50-euro tip because I would have felt bad not paying anything after the waiters were all so nice and accommodating with us). One driver even stopped to buy us "the best Italian ice in all of Italy." Just for the record, they never expect tips in Italy, but I still always gave them one because it just feels wrong to me to get a service for nothing. And lastly, the hotels that Avventure Bellissime picked out for us (mostly five-star hotels, but we had one four-star hotel within the five we stayed at), were all very well located, super nice looking and central to all our activities -- we stayed one tiny walking bridge away from Piazza San Marco in Venice, on a cliff-side hotel overlooking the ocean in Sorrento, in a Tuscan castle overlooking a beautiful garden in Siena, right next to the Basilica of Santa Maria Novella in Florence (where we'd have people with great voices singing love songs on the street at night for tips), and the only-four star hotel we stayed at was the Diplomat in Rome, which was just a short walk from most everything we wanted to do while there. All these years later, my wife still talks about how awesome and amazing that trip was, so I would definitely recommend this company to anybody considering using them. Thank you all again for making that special occasion that much grander for us, and I wish we never had to take that beautiful boat ride from the Grand Canal in Venice to Marco Polo Airport to head back home because your country is just so beautifully amazing. Grazie!

9. Chianti and Castle Tour from Siena

53100 Siena, Province of Siena, Italy My Tour in Italy
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4.6 based on 43 reviews

Discover the beauty of the Tuscan countryside on this 5-hour tour. Visit two wineries and learn about the process of wine-making. Enjoy a variety of tasting opportunities including wine and oil. Spend free time in the medieval village of Monteriggioni.

Inclusions: Hotel pickup and drop-off, Travel by air-conditioned minivan, Expert multilingual guides, Wine, oil and balsamic vinegar tasting, Snack (sliced cured meats and salami), Visit of an ancient Castle

Exclusions: Gratuities

Reviewed By Oversunsetplain

I couldn’t put correct date on this review - I did this tour with my two children in August 2019 and originally posted it then. I have had a message to say that I had posted it under the wrong company (one with a very similar name). I would like to re-post the review as we had such a brilliant day with our guide and would like to recommend the tour company to others whenever this type of activity goes ahead again! Our guide Ms Ivanova was very knowledgeable and friendly. The tour took in many places around the city and we also visited the Uffizi in the afternoon. I was with my children aged 6 and 9 and both really enjoyed this day. They felt included and learned a lot. The guide met us at the times planned and gave plenty of opportunities for questions and were able to answer any queries. Everything was organised well and went smoothly. We were unable to book a tour inside the Duomo but actually this one which took us all the way around the outside and to other fascinating parts of the city was perfect for my family.

10. San Gimignano, Chianti, and Montalcino Day Trip from Siena

53100 Siena, Province of Siena, Italy My Tour in Italy
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4.6 based on 30 reviews

Enjoy a wine tasting and light lunch in a winery on a full day tour of the Tuscan countryside. Visit San Gimignano a real jewel famous thanks to its stunning towers and discover Orcia Valley with a visit to Montalcino, known all over the world for the production of Brunello di Montalcino.

Inclusions: Pick up service, Travel by minivan with air conditioning for a maximum of 8 people, Expert multilingual escorts, Wine tasting and Light Lunch consisting of typical Tuscan dishes, Snack with sliced cured meats and typical salami, Drop off service

Exclusions: Gratuities

Reviewed By Oversunsetplain

I couldn’t put correct date on this review - I did this tour with my two children in August 2019 and originally posted it then. I have had a message to say that I had posted it under the wrong company (one with a very similar name). I would like to re-post the review as we had such a brilliant day with our guide and would like to recommend the tour company to others whenever this type of activity goes ahead again! Our guide Ms Ivanova was very knowledgeable and friendly. The tour took in many places around the city and we also visited the Uffizi in the afternoon. I was with my children aged 6 and 9 and both really enjoyed this day. They felt included and learned a lot. The guide met us at the times planned and gave plenty of opportunities for questions and were able to answer any queries. Everything was organised well and went smoothly. We were unable to book a tour inside the Duomo but actually this one which took us all the way around the outside and to other fascinating parts of the city was perfect for my family.

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