Monteriggioni Culture & history

Our most recommended Monteriggioni Culture & history

Siena, San Gimignano and Chianti with Wine Tasting and Lunch

1. Siena, San Gimignano and Chianti with Wine Tasting and Lunch

Along the way that will lead you to Siena, stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries. It is renowned for its tall towers, wonderful frescoes and many other valuable works of art.  Here, be led to the heart of the historical center, where you will have free time to explore. Following San Gimignano, stop at the charming historical hamlet of Monteriggioni, an amazing medieval village enclosed by its famous walls, which have remained standing to this day.  Enjoy some free time to visit this village. Then, crossing the gently rolling Chianti hills, arrive at a small and typical winery where you will taste 4 fantastic wines and sample balsamic vinegar and locally produced delicacies. Upon arrival in Siena, after free time for lunch, meet your local guide. Take a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo.  Walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the Museum and Oratory of a Contrada (when open), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race.  The Museum of a ”Contrada”, as well as its Oratory, is therefore the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public.  If you wish, your tour can include a guided visit inside the famous Siena Cathedral, built in the 12th century, to discover the beauty of its treasures and works of art.

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

2. Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

Full-Day Excursion to Siena, San Gimignano & Chianti

3. Full-Day Excursion to Siena, San Gimignano & Chianti

Enjoy a full-day excursion by minivan to see the beautiful Chianti area and to visit the cities of Siena and San Gimignano.  Depart at 9:00 AM from Piazza Cavalleggeri, the meeting point located in the city center of Florence. Stop at Piazzale Michelangelo for few minutes to see the splendid panorama and then in one hour you will arrive in Siena. Take a guided tour of the city center, including Piazza del Campo and the Cathedral. There is free time to walk by yourself in the narrow and ancient streets.  Then leave Siena to arrive in Monteriggioni, an old Medieval little village. After a short stop, continue to San Gimignano where you will have free time to explore the city center on your own. San Gimignano is famous for its towers, vernaccia wine and its characteristic craft articles.

San Gimignano and Volterra: Day Tour from Siena

4. San Gimignano and Volterra: Day Tour from Siena

Start your day tour with a scenic drive from Siena to San Gimignano. Stop in Monteriggioni to see the well-preserved fortress built in the 13th century. Explore San Gimignano, admiring its many medieval towers. Recently listed by UNESCO, the town also boasts numerous artisanal boutiques. Head to a small family-run farm to enjoy lunch made with the farm’s seasonal products. Taste dishes prepared with saffron, and accompanied by Vernaccia wine. Continue to Volterra, stopping at a small alabaster workshop to see the ancient art of sculpting. In Volterra, admire the harmonious blend of Etruscan, Roman, Medieval, and Renaissance styles as you walk along the streets of the historic center.

Best of Tuscany Full-Day Scenic Tour from Florence

5. Best of Tuscany Full-Day Scenic Tour from Florence

Enjoy a sightseeing tour of the towns, villages, and countryside of Tuscany on a full-day private excursion from Florence, and travel back in time to the days of the Romans, Etruscans and Middle Ages. You will start by driving to Pisa, a gentle town that recalls the days of the Pisan Republic. The focus will be on the astonishing Piazza dei Miracoli (Square of Miracles), home to the medieval Duomo, Baptistery, and legendary Leaning Tower. Continue to the Etruscan village of San Gimignano, famous for its Vernaccia wines and medieval towers. Stroll the narrow streets of this pearl of Middle Aged Tuscany, before driving to the walled settlement of Monteriggioni, built in the 13th century by the Sienese to keep watch over the Roman Via Cassia from its hillside location. Siena is the next stop, where you will tour the romantic center, best known for the annual Palio horse race in the shell-shaped Piazza del Campo. The city’s medieval skyline is dominated by the Gothic cathedral and taut needle of the Torre del Mangia. Also not to be missed is the Palazzo Pubblico, home to an important museum, and a great work of architecture in its own right. On the way back to Florence, see the charming Chianti area, characterized by rolling hills dotted with vineyards, cypress trees, olive groves, and small hamlets. You will stop at Panzano and Greve, 2 of the most beautiful Chianti towns. And, time permItting, break at a winery to taste world-famous Chianti wines and locally produced extra virgin olive oils.

Other Sightseeing Options in Monteriggioni

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What people are saying about Monteriggioni

Overall rating

4.5 / 5

based on 1,022 reviews

This was definitely one of the top highlights of the trip. Jon was a wonderful and knowledgeable guide, and everything was perfectly planned out. We had ample time in each place and at the winery to see everything we needed to see.

Thank you to Marta and Lido for making our tour entertaining, informative, and comfortable. Recommendations for wine, gelato, and boar were spot on and much appreciated.

Excellent experience! I highly recommend buying this tour. I did it with the CAF Tour team and the guide Marco is amazing!!!! It was all excellent! Super nominate!

It was wonderful and well worth it. Our guide, Vincenzo, was great and didn’t crowd u. Gave great info and let you explore independently. Highly recommend it.

Great trip, especially Siena and local guide there.