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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. 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. Sample Menu  - Appetizer: cold cuts ( prosciutto, finocchiona, salami ) bruschetta olive oil and truffle oil pecorino cheese with balsamic vinegar and green salad - Main Course:  penne with meat ragout and parmesan cheese - Dessert: homemade tart with jam and vinsanto

From Florence: San Gimignano & Siena Tour with Wine Tastings

3. From Florence: San Gimignano & Siena Tour with Wine Tastings

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.

From Siena: Chianti and San Gimignano Sunset Tour

4. 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.

From Siena: San Gimignano, Montalcino & Wine Tasting

5. 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.

Full-Day Excursion to Siena, San Gimignano & Chianti

6. 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.

Siena: Half-day Guided Hike to Monteriggioni

7. 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 first plotted by the Archbishop Sigeric of Canterbury on his return from Rome in the 9th century. The route was considered the main artery to Rome throughout the Middle Ages and is still a popular trail today. Once a highway of men and emotions, a spiritual pilgrimage as well as wealthy trade route, the via Francigena had been forgotten and almost entirely relegated to history by modern roads and only recently brought back to the grip of modernity, enjoyed by many modern pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in the wonderfully preserved castles, villages and ruins along the route.   Pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni, a medieval fortress built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence, today a fortified but quaint village with many shops of local crafts and products.   Once in Monteriggioni, enjoy a guided tasting of local wines before saying goodbye to your guide. You can then remain to explore the village and the surrounding area further at your own pace or return to Siena right away, as you are given bus tickets to return to Siena in your own time (several return buses available throughout the afternoon).

Siena San Gimignano Private Full-Day Tour by Deluxe Car

8. 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 Rome: Tuscany & Siena with Wine Tasting and Lunch

9. From Rome: Tuscany & Siena with 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.

Chianti and Castles Tour From San Gimignano

10. 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 a wine tasting at a winery in the 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.

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What people are saying about Monteriggioni

Overall rating

4.6 / 5

based on 329 reviews

Tour was extremely value for money. There was only six of us. Meeting point was easy to locate. Our guide, Vincenzo (not sure if I got the name and/or spelling right) was very amiable and experienced. One thing though, I wouldn’t suggest going for the lunch (though the price difference is really negligible). Not that the lunch was bad, it was worth the penny paid but its not everyday that you get to visit Siena. I recommend that you check out other more popular food places in Siena to make the most of your time. Winery we visited was mediocre but nothing to complain about for the price point. If you’re in tuscany for the winery, look elsewhere or go on your own. This experience is suitable for people who want to visit the towns :)

Hello! The trip was wonderful! Our guide Sandro was attentive, cheerful and gave us a lot of information along the route. The chosen itinerary and the proposed objectives are very interesting, and the wine tasting was a unique experience. Leonardo, our coach driver very nice, attentive and very professional. Many thanks to the whole team!

Great tour, we loved it! Constantine was a fabulous guide and Leo was an awesome driver! He was very helpful with pointing out great local places to shop and eat. We highly recommend this tour! One of our favourite days in Italy.

The tour guide was great. Very informative and you could tell he loved his job. Lunch at the winery was delicious, and wine was excellent. Great tour would definitely recommend.

Totally worth it! The destinations, the winery and for sure our guide Sandro made our day pleasant. 100% recommend and if you have the choice ask for Sandro as your guide!