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Monteriggioni

UNESCO sites

Our most recommended Monteriggioni UNESCO Sites

Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

1. Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

Discover Tuscany on a guided day tour from Florence to the medieval cities of Siena, San Gimignano, and Monteriggioni. Enjoy views of rolling hills and vineyards, with a stop at a Chianti winery for a traditional Tuscan lunch and wine tasting. First arrive in San Gimignano, a tiny medieval town that has remained intact through the centuries. Sitting upon a hilltop, it is famous for its numerous towers, frescoes, and other art treasures. Enjoy more free time to discover this fascinating city on your own. Next, visit the charming historical hamlet of Monteriggioni, a medieval village enclosed by its famous walls, which remained standing to this day. Afterward, you will cross the Chianti rolling hills and then arrive at a small and typical winery. There, taste 4 wines, and sample balsamic vinegar and other locally produced products. Your final stop is in Siena, where you will have free time to walk along the narrow medieval streets, admiring the splendid palaces, the Cathedral, Libreria Piccolomini, and the famous shell-shaped Piazza del Campo.

From Siena: San Gimignano, Montalcino & Wine Tasting

2. From Siena: San Gimignano, Montalcino & Wine Tasting

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation. The final stop of the day will be a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines. Sample other typical local products as well.

Chianti and Castles Tour From San Gimignano

3. Chianti and Castles Tour From San Gimignano

Immerse yourself in the picturesque Tuscan scenery on a sightseeing trip to the beautiful region of Chianti. Visit the Castellina in Chianti before enjoying wine tasting at a winery in the Chianti area. The beautiful ruby-red color and the characteristic bouquet with scents of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine results from the wise blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. On this trip, discover the breathtaking, uncontaminated landscapes that have been cradling the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in the hills of this region. The sounds, scents, and flavors of this land will capture your senses through a unique experience. Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Later, move on to a winery in the middle of the Chianti Classico area, where you’ll have a wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

From Rome: Siena, Chianti, Wine Tasting and Lunch

4. From Rome: Siena, Chianti, Wine Tasting and Lunch

This tour has been designed to showcase the very best of Tuscany in just one-day and is perfect for travelers who only have a short amount of time. The day begins with departure from Rome at 6:45am on a fast speed train to Florence. Upon arrival in Florence, head to the meeting point sent to your email to meet your guide and set out on your sightseeing adventure. The first stop of the day is the historic city of Siena, which is bursting with rich architectural styles, best showcased at the cathedral and the old palace. After a brief guided walking tour of Siena, enjoy free time to explore on your own. Wander around the quaint streets of this magical town, have a traditional Italian lunch at one of the many cafés, or shop for handmade crafts and souvenirs. Continue the tour to the walled town of Monteriggioni next, which was the filming location of the blockbuster movie, Gladiator. Arrive at the UNESCO World Heritage Listed San Gimignano next, which is the most famous walled medieval town in Tuscany, and nicknamed the ‘Manhattan of Tuscany’ due to its many towers. Armed with tips and recommendations from your guide, head out on your own adventure in the town and visit the sights and attractions that interest you most. Don’t forget to stop by the store of the world-champion gelato maker, and treat yourself to a seriously sweet treat. During the day, ride through the rolling countryside of Chianti and soak up the charming scenic views on the way to an authentic Tuscan winery. Against the backdrop of luscious vineyards and olive groves, enjoy a spectacular lunch with a wine and olive oil tasting session. At the end of a truly unforgettable day, head back to Rome, arriving at approximately 8 PM.

Florence: Private Siena, San Gimignano and Chianti Tour

5. Florence: Private Siena, San Gimignano and Chianti Tour

Explore the beauty of Tuscany in this tour from Florence to Siena, Castello di Monteriggioni, Chianti, and San Gimignano. Visit medieval towns and villages, and drive through idyllic vineyards, with the option to stop at an organic farm and winery for lunch. Meet your friendly guide at your accommodation and drive in an air-conditioned minivan to see the distinguished medieval architecture in Siena, like the seashell-shaped Piazza del Campo and Siena Cathedral before enjoying a scenic drive to Castello di Monteriggioni. Enjoy the small, fortified village and take a short stroll after lunch at one of the local restaurants. Travel along the Chianti wine road which is rich with castles and villages with a stop to admire a small medieval village surrounded by endless vineyards. Experience a unique dining setting while taking in an amazing Tuscan panorama with lunch at an organic farm in Castellina, with the lunch option. Journey to historic center of the picturesque medieval town of San Gimignano and see its ancient towers.

Siena & San Gimignano Day Tour & Wine Tasting from Rome

6. Siena & San Gimignano Day Tour & Wine Tasting from Rome

Visit the cities of San Gimignano and Siena on a full-day trip from Rome. Begin by crossing the beautiful hills of Chianti to arrive first in San Gimignano, a picturesque, fascinating, medieval town declared a UNESCO World Heritage Site, and famous for its white wine, the world-renowned Vernaccia. You will have time to wind your way through the narrow streets and admire the landscape surrounding the village. Then continue to Monteriggioni, a medieval town with well-preserved walls and towers. Here you can taste Chianti red wine along with homemade snacks. Finally, make your way to Siena and visit the historic center, also a UNESCO World Heritage Site. See Piazza del Campo, one of the most splendid examples of Gothic civil architecture in the world. View the magnificent Palazzo Pubblico with its bell tower, Torre del Mangia. Then walk to the Siena Cathedral, a church representative of Italian Romanesque-Gothic architecture. In the late afternoon, begin your return trip to Rome.

From Florence: 4-Day Tuscany Highlights Tour

7. From Florence: 4-Day Tuscany Highlights Tour

Day 1: After checking in to your hotel, begin your day with a guided tour of the Uffizi Gallery and learn more about the oldest and most famous art collection in the world.  Following the Uffizi, join a tour of Florence's most iconic streets and squares with a professional guide. Stroll through the stunning Santa Maria del Fiore Cathedral, the Old Bridge, the Signoria Square with its replica of Michelangelo’s David, the Republic Square and more. Day 2: Crossing the beautiful Chianti hills, arrive at the walled town of Monteriggioni. Drink in the town's century-old history and relive the Medieval atmosphere before continuing to Siena, famous for its splendid examples of Gothic architecture, and enjoy a light lunch in a cozy restaurant where you can try traditional Tuscan products.  Next, drive to San Gimignano, a UNESCO World Heritage Site famous for its wine. At the end of the day, head to the Chianti area and marvel at its picture-perfect landscapes. Sample the region's best red wine in a rustic wine estate along with home-made aperitifs and olive oil tastings. Day 3: After breakfast, begin the journey to Cinque Terre National Park for an unforgettable day in one of the most enchanting landscapes in the world. Discover five villages suspended between sea and land, where you can sunbathe or swim in one of the area's many beaches before taking the boat to Vernazza, a seaside town surrounding a small natural port. Day 4 Today, enjoy a guided tour of the Florentine Dome and enjoy panoramic views of the entire city from its peak. Afterward, enjoy a guided tour of the Accademia, where you can see Michelangelo's masterpiece, David.

Siena, San Gimignano and Chianti Experience

8. Siena, San Gimignano and Chianti Experience

Explore the essence of Tuscany: Siena, San Gimignano and Monteriggioni are waiting to be discovered. The first step is Siena. Here, be welcomed by a local guide that will lead you through the most typical spots such as Piazza del Campo and Piazza del Duomo, where you can appreciate the authentic medieval atmosphere which makes this town special and unique. After that you will have an hour of free time that you can spend to visit the Duomo, do some shopping or simply enjoy the local deliciousness. Back in the minivan, head to the lovely town of Monteriggioni. Built in 1213, its fame was so big that the great poet Dante Alighieri made a sign to his round enclosure in the Divine Comedy. Here, finally, have lunch in a typical restaurant and have the chance to taste local food and wine. In the afternoon, reach San Gimignano, where you will have free time to discover the town and admire the amazing landscape. The city of beautiful towers, has been nominated as a UNESCO world heritage site as an example of a medieval town. At the end of the visit, come back to Florence in full comfort just in time for the sunset.

From Florence: Private GUIDED tour, Siena & San Gimignano

9. From Florence: Private GUIDED tour, Siena & San Gimignano

• Stop At: Siena, Tuscany. Experience Siena through the expert and knowledgeable lens of a professional tour guide! Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore with your guide Siena’s rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts! Duration: 3 hours • Stop At: Castello di Monteriggioni, Tuscany. Make a lovely stop in the small, fortified village, which is still surrounded by its original medieval walls. Located not far from Siena, Monteriggioni is a great spot for a short walk after lunch at one of the local restaurants. Duration: 2 hours • Pass By: Village of Fonterutoli, Siena. Fonterutoli has been an important village ever since the Roman times. The Via Romea passes here, and is still today traveled by pilgrims from all over the world. Location of the historic Mazzei family since 1435 (for 24 generations), the village of Fonterutoli maintains its medieval appearance intact. Stroll in the village to stretch your legs and take some beautiful photos. Duration: 30 minutes •Stop At: Organic Farm/Winery Tenuta Casanova, Tuscany. (*optional) *OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will show you around the property, his wife will prepare a delicious and unforgettable lunch for your private group. The owner will show you to his cellar to admire his Super Tuscans and Chianti Classico wines -Craft Wine- and to the nearby Acetaia, a vinegar cellar, with old vinegar. Afterwards, experience a unique dining setting while taking in an amazing Tuscan panorama. You will taste organic specialties, such as the typical Lasagna with traditional sauces, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses seasoned with an incredible aged balsamic vinegar. Wine will accompany this lunch every step of the way. Each of the four main courses and desserts will be paired with a different and distinctive glass of wine. We will conclude with ice cream and balsamic vinegar or other desserts. (This option will slightly reduce your time to visit the cities of Siena and San Gimignano, and exclude the possibility to visit the fortress of Monteriggioni). Duration: 2 hours •Stop At: Historic Center of San Gimignano, Tuscany. The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany. San Gimignano is a treasure of medieval architecture, frozen in time at 1300 AD. Above all, it is famous for its ancient towers, which still stand out from its skyline, earning it the nickname Manhattan of the Middle Ages. This is the last destination of the day, before returning to Florence. Duration: 1h30m

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Frequently asked questions about Monteriggioni UNESCO Sites

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Other Sightseeing Options in Monteriggioni

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What people are saying about Monteriggioni

Overall rating

4.5 / 5

based on 57 reviews

The guide (Kike ?) gave us the necessary information for each spot we visited and gave some useful tips along the way. The driver (Leonardo) was the perfect and smoothest driver I ever had on a tour. The bus was clean and air-conditioned (which was important on a hot sunny day). We stayed exactly the right amount of time at each spot (although a thorough visit of Siena would require at least a day in my opinion so don't expect to see everything, this is a "bullet point tour"). The highlight was the meal and wine tasting experience (which is one and the same thing). The meal had three courses as promised and did fill us up for the next leg of the journey. The wine was great and the "entertainer" at that spot was amazing ! The cat at the entrance was also a great addition

A fantastic day was had by all. Well worth the money, our guide was amazing. Each place was as spectular as the next. Lunch at Chanti was delicious and wines, vinegars etc, were explained really well by the host.

We had a great day. Great driver, great wine tasting and gorgeous villages and scenery, definitely recommend.

Nice tour, Lisa is the excellent tourguide. Definitely deserves for the money and I recommend.

A fantastic tour and a highlight of our holiday in Siena!