Monteriggioni
Castle & Palace Tours

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Our most recommended Monteriggioni Castle & Palace Tours

From Siena: San Gimignano, Montalcino & Wine Tasting

1. 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.

Siena: Half-day Guided Hike to Monteriggioni

2. 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.

Chianti and Castles Tour From San Gimignano

3. Chianti and Castles Tour From San Gimignano

Experience the region of Chianti and immerse yourself in picturesque Tuscan scenery on this guided, multi-stop trip from San Gimignano. Visit ancient churches, medieval castles, and small villages where the rhythms of traditional life remain unaltered. Stop at 2 wineries for tours and tastings. Explore the home of one of the most famous wines in the world, with its beautiful ruby-red color and characteristic violet-scented bouquet: Chianti. This wine results from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. Get picked up directly from your accommodation in San Gimignano, then set out to discover the breathtaking landscapes that have cradled the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in this region. After some sightseeing, the tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and you'll take part in a guided tour of the castle gardens. When the tour of the garden ends, enjoy a tasting of two different wines. During this tour, you'll see the characteristic Castle of Brolio from the outside as well as the inner garden of the castle. Later, move on to another winery in the middle of the Chianti Classico area, where you'll savor a second wine tasting paired with extra virgin olive oil. The tour ends with drop-off back in San Gimignano.

Florence: Private Siena, San Gimignano and Chianti Tour

4. 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.

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What people are saying about Monteriggioni

Overall rating

4.4 / 5

based on 886 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!

Great company although we didn't know each other; driver-guide (Carlo) courteous and helpful. visited two different wineries but with excellent hospitality and excellent wines. Clear presentation. Close-knit and fun group. San Gimignano beautiful and fascinating, short time but only 90 minutes. Montalcino also a beautiful town adequate time for the visit.

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.

The best tour ever!! Our guide even added a stop to another very tiny Tuscan town.