Monteriggioni
Architecture Tours

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Our most recommended Monteriggioni Architecture Tours

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.

Chianti and San Gimignano Sunset Tour from Siena

2. Chianti and San Gimignano Sunset Tour from Siena

Explore the notable wine region of Chianti on a full-day sightseeing and wine tasting tour from Siena. Travel in a small group of no more than 8 people, and enjoy comfortable transfers by air-conditioned vehicle. Depart Siena in the early afternoon, and drive past the vineyards of the Chianti wine lands. See dense forests of oak wood and cypress trees, neat rows of vineyards, and landscapes shaped into works of art by the combined forces of nature and mankind. Go to a Chianti wine estate to tour the grounds and wine cellars. Learn the winemaking process before sitting down to a tasting of Chianti Classico wines and olive oil. Next, descend to the medieval fortress of Monteriggioni, and marvel at its intact ring of walls and turrets. Built in the 13th century, Monteriggioni was mentioned in Dante’s “Divine Comedy.” As the sun begins to set, travel to the legendary village of San Gimignano to enjoy the romantic town after the daytime crowds have departed. Admire the medieval towers at a leisurely pace, and enjoy some free time to visit the cathedral or Civic Museum. Shop for souvenirs in the many leather and hand painted pottery stores. Sample the local produce at food shops and wine bars. Depart San Gimignano for a Tuscan dinner at an organic farm in the countryside. Taste the wines of San Gimignano, such as the notable Chianti red, Vernaccia. Weather permitting, dinner will be served on a terrace overlooking the cultivated fields and skyline of San Gimignano. Watch the sunset as you dine, before your return transfer to Siena.

Siena: Half-day Guided Hike to Monteriggioni

3. Siena: Half-day Guided Hike to Monteriggioni

Give your mind a rest from the noise of the crowded towns, follow your expert guide on a pleasant walk along the Via Francigena, an ancient pilgrim route for the first time plotted down by the Arcbishop ‘Sigeric the serious’ of Cantebury on his return from Rome in the 9th century and considered the main artery to Rome throughout the middle ages. This route, that has for centuries been a highway of men and emotions, a spiritual pilgrimage and a wealthy trade route, has been forgotten and almost entirely relegated to history by the modern paved car roads. Only recently the route has been brought back from the grip of modernity and is today enjoyed by many pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in it's wonderfully preserved castles, villages and ruins.  See the Tuscany you would never want to miss before returning home, pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni. A medieval walled town located on a natural hillock, built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence.  Once in Monteriggioni, enjoy a guided tasting of local organic wines before saying goodbye to your guide for the end of the tour. Feel free to explore the village and the surrounding area at your own pace. You will be given a bus ticket to 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.

Siena San Gimignano Private Full-Day Tour by Deluxe Car

5. Siena San Gimignano Private Full-Day Tour by Deluxe Car

Explore Tuscany on this tour of quaint towns and cities. After pick-up from your hotel, the tour will make its first stop in Monteriggioni. Here you can explore a medieval walled town built by the Sienese in the early 13th century. The tour continues to Siena where you will discover one of the most beautiful cities of Tuscany. Siena is famous for its annual historic horse-race, the "Palio," and for its Duomo, an art-filled cathedral that features works by Michelangelo and Donatello. Make your final stop in San Gimignano, one of the most charming and picturesque Tuscan hill towns. Medieval towers dominate the landscape of this UNESCO World Heritage town in a manner that is strikingly similar to the skyscrapers of our modern cities. During the day, you will have the option to stop in a local restaurant for lunch.

From Florence: Siena, San Gimignano & Chianti Private Tour

6. From Florence: Siena, San Gimignano & Chianti Private Tour

Amongst the vineyards and olive groves of Chianti, lie medieval towns and UNESCO heritage sites. Explore them all on a private, 8-hour tour of the Chianti countryside, Siena and San Gimignano. A truly private tour, you will begin your day with complimentary pick-up at your Florence hotel by chauffeured private vehicle. Your English-speaking driver is at your disposal for a maximum of 8 hours. Your first stop will be in Siena, a medieval town. Here you will meet with your private tour guide, who is at your disposal for a maximum of 2 hours. Your guide will take you through the historic city center, where you may admire the splendid palaces and other points of interest. Your tour of Siena will conclude in the Piazza del Campo, one of the most beautiful piazzas in the world. Here, you will find the Palazzo del Comune and have some free time to enjoy lunch. The journey to your next stop, San Gimignano, will take you through Chianti territory. Along the road you will find panoramic vistas, as well as lush vineyards and olive groves. Along the way to San Gimignano you may wish to stop and admire the fortified hamlet of Monteriggioni. This hamlet is a small jewel built in the 13th-century and still embraced by ancient walls. San Gimignano you will find is a UNESCO designated world heritage site. Here you will be given free time to take in the historically interesting medieval town planning, as well as the numerous towers. You will soon find out why this place is called the “Manhattan of the Middle Ages”. Touring this extraordinary region of Italy is a wonderful experience and the fact that this tour is entirely private makes it even more special.

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.

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What people are saying about Monteriggioni

Overall rating

4.6 / 5

based on 329 reviews

A wonderful tour! We had a lot of fun and joy with our guide Kiko. Kiko went to great lengths to bring the country and the people closer to us. It was very exciting to learn things from the past and from the present time. Wild herbs along our hike on the pilgrimage route and anecdotes from the past made the hike very entertaining. The path was very pleasant to walk. In Monteriggioni we had a very nice wine tasting. We really liked the wine, so we even ordered delivery to our home. Afterwards we had a very good meal in the nice little place. We would have loved to have stayed there. I highly recommend this tour! Thank you dear Kiko!

Bus driver and guide in the bus were very kind and informative. The lunch was unexpectedly large. 3 course meal with typical plate of cheese, salami, ham, olive oil and salad. This was the highlight. Main course was macaroni Bolognese and a small piece of cake as last course. Vegan and vegetarian is also possible. Then we could taste 4 different wines. So lunch was way better than expected. The trip to San Gimignano and Montereggioni were well timed. Enough to see the highlight. Same for Siena. We didn't book any guide in Siena and that was fine as well. I can definatly recommend this journey.

Great 3 hour morning hike with personable and naturalist oriented guide. Lovely lovely scenery. We would have preferred a bit more background on the Via Francigena. Winery to end with was great - we bought the winery’s artisan cheese to go along with the bread and Chianti. Overall, an excellent experience and great value!

Very nice easy hike with many beautiful views of the countryside. Very good hiking guide, who also gave the participants a lot of information about nature, the country and the landscape.

Great day! We’ll worth the money! Siena is a beautiful place and the lunch was fantastic! Marta was the perfect tour leader!!