8 Walking Tours in Monteriggioni That You Shouldn't Miss

April 12, 2022 Randal Brittian

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. Private Tour: Guided Hike in Tuscany with Transport from Siena

Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Tuscan Escapes
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5.0 based on 5 reviews

Explore Tuscany's picturesque rolling hills on a private, full-day hiking tour with transport from Siena. With your expert guide, enjoy a scenic, full-day adventurous hike through the beautiful Chianti region in Tuscany, full of forests, olive groves, vineyards and quaint villages, stopping halfway to relax over a picnic of classic Tuscan specialties. Continue in the afternoon by minivan to the medieval hill town of San Gimignano for a walk around its UNESCO World Heritage-listed city center. Spend time at your leisure browsing the main sights and boutique stores in this gorgeous town before your relaxing drive back to Siena.

Inclusions: Private guide, Round-trip transportation from Siena to Chianti, Transport by air-conditioned minivan (maximum 8 passengers), Picnic lunch with glass of wine, Hotel pickup and drop-off

Exclusions: Gratuities, Food and drinks (unless specified)

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.

2. Siena, San Gimignano and Monteriggioni: Medieval Tuscany Experience

Via del Trebbio, 8r, 50123 Firenze FI, Italy Keys of Italy
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5.0 based on 5 reviews

Discover 3 of the most authentic towns nestled in the heart of the tuscany countryside. Siena, the famous Palio city, San Gimignano, UNESCO heritage and Monteriggioni, one of the most enchanting italian walled town. "Explore the essence of Tuscany:Siena, San Gimignano and Monteriggioni are waiting to be discovered!!!" WHY CHOOSE US? Secure bookings, Guaranted Departures! 48 hours Cancellation policy, best rates guaranted! Group of maximum 8 people.

Inclusions: Professional guide in Siena, Free time in all the cities, Luxury van at disposal, Semi private tour, Lunch, Air-conditioned vehicle

Exclusions: Hotel pickup and drop-off, Gratuities

Reviewed By E1429NCbarbaraf

Apartments by Fair Winds tour operator. We had booked an apartment for April 2021 and due to Corona virus we had to cancel. Despite the financial difficulties of these times we received a refund this month and found the company very amenable and willing to bring to Florence the good reputation it deserves.

3. Full day to San Gimignano, Siena and Chianti with Lunch and Wine Tasting

Florence, Florence (Villa Costanza Tram T1), 50018 Scandicci, Metropolitan City of Florence, Italy My Tour in Italy
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4.5 based on 632 reviews

Enjoy a full-day tour into the heart of the beautiful Tuscan countryside. Visit the town of San Gimignano, the wine territory of Chianti, the medieval town of Siena and the Monteriggioni fortress.

Inclusions: Travel by GT air-conditioned coach, Expert multilingual escorts, Guided Tour of Siena with monolingual guide in English or Spanish , Typical lunch in Chianti area accompanied by Wine tasting, Free time in San Gimignano, Visit of Monteriggioni fortress

Exclusions: Hotel pickup and drop-off, 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.

4. Siena, San Gimignano and Chianti tour

Piazzale Montelungo, Firenze FI, Italy Albatravel Florence Day Tours
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3.3 based on 3 reviews

Spend a memorable day touring Tuscany. You’ll sample Chianti wines and Tuscan foods and enjoy the scenic landscape of vineyards and olive groves. Visit Romanesque churches, farmhouses, castles, and medieval city squares on this full-day excursion.

Inclusions: Wine tasting, 3-course lunch, Live commentary on board, Professional guide, Alcoholic Beverages

Exclusions: Hotel pickup and drop-off

Reviewed By K00lK00kie

I walked straight from plane to exit - but driver didnt wait for me. I was not late! They were unable to offer a later shuttle. Told to get a cab.. disgusting service. Have not offered a refund and after no response from Expedia. I am now trying to dispute this via my credit card company.

5. Discover Tuscany Private vehicle Full day tour from Florence.

Firenze Santa Maria Novella railway station, P.za di Santa Maria Novella, 50123 Firenze FI, Italy Moro Tuscany Travel

This is a private tour with a private vehicle so relax while we are crossing the beautiful Chianti hills we arrive at the Medieval hilltop gem of Monteriggioni, with its beautiful walls. Here you can enjoy the history and relive the atmosphere of olden times. Our beautiful day will continue in Siena, famous for its splendid examples of Gothic architecture and the Palio horse race. We will visit the suggestive Piazza del Campo with its Torre del Mangia. Visit Piazza del Duomo and be impressed by the imposing Cathedral, one of the finest achievements of Italian Gothic. Before leaving Siena, you will discorver local shops where, together with genuine Tuscan products wines, and Traditional Tuscan lunch. Next stop will be SAN GIMIGNANO, famous for its white wine, the world renowned Vernaccia, and its mediaval towers, also declared a World heritage Site by UNESCO! The visit is free for independent sightseeing, strolling around the narrow streets and admiring the relaxing landscape.

Inclusions: Air-conditioned vehicle, Private transportation, Bottled water, Lunch, Personal Shopping assistance, Wi-Fi on board, Licensed Tour Guide , Possibility to customize your tour, Free pick up from Florence Airport (if requested)

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6. Kid-Friendly Siena & San Gimignano Day Tour from Florence w/ Driver & Guide

Raphael Tours in Florence

Explore the heart of Tuscany on this full-day kid-friendly excursion through the cities of San Gimignano and Siena. Expect to see the gorgeous Tuscan countryside and two very different, yet both equally beautiful cities and both listed as UNESCO World Heritage Sites. Get picked up from your centrally located hotel in Florence and head towards Siena, known for the Palio horse races in Piazza del Campo. Learn all about the history of the area and the architectural jewels like the cathedral, which represents one of the most important examples of Gothic architecture in Italy. Visit the small, medieval, and walled town, Monteriggioni, before heading to San Gimignano. This charming hilltop village is known as the "City of a Thousand Towers", though only 14 can be seen today. Climb the bell tower to get marvelous views and take in the many sights as you wander around. Kids will be engaged with activities throughout and everyone will go home, knowing more about this fascinating region.

Inclusions: Private transportation

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Reviewed By kix2mix2

It was a nice walk around the city, and the guide was also very nice. I think it was somewhat lacking in information, like the tour could have been a bit more filled with nuggets of information... But maybe i'm just picky! it was a rainy day so part of the time we were sheltering from rain :)

7. Private Transfer from Rome to Florence: stops in Orvieto, Siena & Monteriggioni

Vatican Tours inc

The safe and comfortable door to door transfer in chauffeured air conditioned Mercedes E-Class ( 2 pax) or V-Class ( max. 7 guests ) from Rome to a hotel in Florence. Umbria and Tuscany with a stop in Orvieto, Siena for a guided or self guided visit and Tuscan village of Monteriggioni. Lunch in a sienese trattoria, at one of the most beautiful square of Italy.

Inclusions: private driver from Rome to hotel or BB in Florence, stop in Orvieto for 1 hour, stop in Siena for over 3 hours for visit and lunch, stop in Monteriggioni for approx. half an hour

Exclusions: gratuity, optional private guide in Siena for 2.5 hour visit at E 240/group

Reviewed By Grainne D

We booked the Underground Colosseum tour in March but then Italy was placed under covid19 restrictions & our trip was cancelled We cancelled our tour a week before it was supposed to happen and contacted the company to request a refund. The CEO Piotr replied and requested that we wait 3 months for our refund due to the financial impact that covid19 had taken on their business. As I work in the hospitality industry in Ireland, I understood their difficulties, so with great trust, we agreed to wait 3 months for our refund. 9 months later, several unanswered phone calls & emails later, I have to accept that we were conned and will never receive our money back. Avoid booking tours with this company as they are crooks!

8. From Florence Private Full Day Tour to Siena, San Gimignano and Wine Country

Vatican Tours inc

Many consider Siena the most beautiful town in Tuscany. Your guide allows you to form your own opinion when you enter this hypnotic hill town. This is a city steeped in history and culture and boasts the monuments, churches and palazzos to prove it. Perhaps the most famous site is the Piazza del Campo where the great horserace "Palio" has been held since medieval times. Your guide points out treasures and allows time for souvenir shopping prior to your picturesque lunchtime break. Then, for a lunch stop on to Monteriggioni, the medieval fortress mentioned in Dante Alligieri's Inferno surrounded today by vines and olives. After a short stop you go to San Gimignano, a high-rise hamlet of the dark ages with more than a dozen stone towers. The narrow streets, charming churches and captivating shops and art galleries make this visit a mind-tattoo of memories. The day will also include the stop at Antinori ultra modern winery, if not for tasting and visit.

Inclusions: private English speaking driver/guide from Florence

Exclusions: lunch , wine tasting at Antinori winery at approx. Euro 20/person, optional private local guid in Siena for 2 hours at Euro E 220/group

Reviewed By Grainne D

We booked the Underground Colosseum tour in March but then Italy was placed under covid19 restrictions & our trip was cancelled We cancelled our tour a week before it was supposed to happen and contacted the company to request a refund. The CEO Piotr replied and requested that we wait 3 months for our refund due to the financial impact that covid19 had taken on their business. As I work in the hospitality industry in Ireland, I understood their difficulties, so with great trust, we agreed to wait 3 months for our refund. 9 months later, several unanswered phone calls & emails later, I have to accept that we were conned and will never receive our money back. Avoid booking tours with this company as they are crooks!

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