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Monteriggioni
Culture & history

Culture & history

Our most recommended Monteriggioni Culture & history

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

1. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and choose a guided tour in your language to learn even more about the historic area. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Begin with Pisa and visit its stunning Piazza dei Miracoli. Admire the Baptistery, the Cathedral of Santa Maria Assunta, and, of course, the famous Leaning Tower of Pisa. After your free time in Pisa, head to a typical Tuscan winery in the Chianti Area and enjoy a delicious lunch with some local wine. Explore the city of Siena and visit to Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. Enjoy your last stop in San Gimignano, a UNESCO medieval town, world-known for its Vernaccia di San Gimignano. The system of towers of San Gimignano tells the glories of the powerful families. Between saffron fields and typical indigenous vineyards, the city knows how to offer postcard views.

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

2. Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

Embark on a scenic guided tour from Florence to the charming Tuscan towns of San Gimignano, Monteriggioni, and Siena. Stroll around the historic villages and enjoy a delicious Chianti Hills wine and balsamic vinegar tasting. Upgrade your experience with tickets to Siena Cathedral. Start at San Gimignano, the world-famous walled town located on a hilltop, which has remained intact through the centuries and is known for its tall towers, frescoes, and many other works of art. Take around 2 hours of free time to explore the city center. Visit the historical walled hamlet of Monteriggioni. Cross Chianti’s rolling hills to a cozy winery where you can relax and enjoy three wines and balsamic vinegar, followed by a Chianti-style three-course lunch. Enjoy a guided tour of Siena’s historic center (if selected in the option), starting with the 13th-century Basilica of San Domenico. Stroll along the narrow medieval streets of the city, flanked by splendid palaces and historic shops. Pass through the Piazza del Campo and visit the cathedral, if you select the option.  Take some free time in Siena before returning to Florence. The order of the visit may change.

From Florence: Siena, San Gimignano & Monteriggioni Tour

3. From Florence: Siena, San Gimignano & Monteriggioni Tour

Experience the charm of Tuscany on a day trip to Siena, San Gimignano, and Monteriggioni from Florence. Try a variety of Chianti wines paired with snacks and admire the picturesque Tuscan hills.  Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT bus. The first stop is at Monteriggioni, a medieval hilltop town that is famous for its intact medieval city walls. After some free time, head to the world famous Siena. Explore the Piazza del Campo, that is known for the Palio Horse Race and for its splendid examples of Gothic civic architecture. Have time to visit the magnificent Palazzo Pubblico.  Arrive in San Gimignano, a medieval town declared a World Heritage Site by UNESCO. Take time to wind your way through the narrow streets and admire the lush landscape. Finally, head to the Chianti area and enjoy postcard-perfect landscapes. Conclude your day at a famous wine estate and taste fine Chianti red wine along with homemade snacks.

From Florence: Chianti Half-Day Afternoon Tour

4. From Florence: Chianti Half-Day Afternoon Tour

Discover the Tuscan wine region of Chianti on a scenic guided tour by van from Florence. Visit a local wine estate, tasting its wines and local produce. Immerse yourself in the surrounding picturesque landscape, with a visit to a medieval village in the region. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Visit a charming Chianti wine estate, enjoy a guided tour of its wine cellars, and gain an insight into the various stages of wine production. Afterward, enjoy some wine tastings. Visit a winery that not only offers a tasting that even true connoisseurs will enjoy with great pleasure, paired with some Tuscan samples, but you will also get to enjoy the wonderful surrounding landscape, immersed in an enchanting and welcoming atmosphere. Visit a real Medieval architecture village in Chianti hills, enjoy some free time to stroll out, and breathe in the local atmosphere. You'll also have the opportunity to buy Italian wine, Chianti Classico, olive oil, balsamic vinegar, cheese, and herbs to take home.

From Florence: San Gimignano, Siena, and Monteriggioni Tour

5. From Florence: San Gimignano, Siena, and Monteriggioni 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. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. 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.

From Siena: San Gimignano, Montalcino & Wine Tasting

6. 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. Visit San Gimignano, 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. Afterwards, stop at a winery for a lunch of salami, cheese, and other local products, accompanied by Chianti tasting.  Discover 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. Finally, enter 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.

San Gimignano and Volterra: Day Tour from Siena

7. 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. 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.

From Siena: Chianti and San Gimignano Sunset Tour

8. From Siena: Chianti and San Gimignano Sunset Tour

Explore the Chianti wine region and the hilltop town of San Gimignano on a sightseeing and wine-tasting tour from Siena. Travel in a small group and enjoy comfortable transfers by air-conditioned vehicle. Depart Siena in the early afternoon, and drive past the vineyards of the Chianti wine lands: neat rows of vineyards, and landscapes shaped into works of art by the combined forces of nature and mankind. Head to a Chianti wine estate to tour the grounds and wine cellars. Learn the winemaking process before sitting down to a tasting of local Chianti wines and olive oil. Explore the medieval fortress of Monteriggioni and marvel at its intact ring of walls and turrets. Travel to the village of San Gimignano to enjoy the charming streets and laneways as the sun begins to set and daytime crowds have departed. Admire the medieval towers at a leisurely pace, and explore the many streets and squares. Visit the boutique stores of local crafts and products. Enjoy a typical Tuscan dinner at a local farm in the countryside. Taste the white wine of San Gimignano, the Vernaccia, or have some local Chianti red wine. Weather permitting, dinner will be served outdoors. Return to Siena after dinner.

Full-Day Excursion to Siena, San Gimignano & Chianti

9. 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.

From San Gimignano: Chianti by E-Bike with Wine Tasting

10. From San Gimignano: Chianti by E-Bike with Wine Tasting

There is no better way than by bicycle to discover the beauty and richness of this part of Italy, sharing in the passion for cycling, art, food and wine. The tour takes place in Tuscany, more specifically, in the magnificent landscapes surrounding Siena. There are, in fact, the most beautiful areas and also the most suitable for a cycling trip through Tuscany. From the seat of your electric bike, you will discover how Tuscany life flow slowly yet incessantly, creating a natural equilibrium among art, culture, and nature. Tuscany is paradise for a cycling tourist, who will be greeted by gently rolling hills embellished with winding dirt roads, curving pathways, vineyards, and shaded country roads. All of these splendors are framed by a surprisingly varied landscape where you will be able to discover abbeys, rural churches and castles. The landscape is characterized by the deep red earth, and alternates between fields of sunflowers and vineyards, and is punctuated by ancient castles and medieval hamlets. Many panoramic views allow you to see all the way to San Gimignano, overlooking forests of beautiful Italian oak and corbezzoli. The tour is crowned with a visit to the splendid medieval for tress of Monteriggioni. 

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What people are saying about Monteriggioni

Overall rating

4.5 / 5

based on 1,022 reviews

This has got to be the best value tour in all of Italy!! My family (w/ 3 teens) had the BEST time with our friendly guide, Naz. We got to see SOOO much of Italy—three stops plus an amazing lunch at a a winery. Naz was very good at sharing interesting information about every stop, making recommendations of highlights, and making sure everyone was having the best time!! The stops in Pisa, Siena, and San Gimignano were amazing!! I couldn’t recommend this tour more!!!

The whole trip was a dream, the guides where very accommodating and even when I was late due to transport issues, they were kind enough to wait for me. I loved the whole itinerary and the information provided was very insightful and useful, I loved it all from start to finish.

Mahnaz and Luciano and Alessio were the best group to see this tour with! Such a fun and loving group and very knowledgeable about the history of Florence! I highly recommend everyone to book this tour and experience Italy to its fullest!!!

Everything was at the exact time. We had a wonderful time enjoying the astonishing scenery. The guides were very helpful, cooperative and very nice. The wine tasting was super and it is worth the money that we paid Such an amazing tour

It was a great way to see Tuscany in a short amount of time. The lunch at the winery was excellent!