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Things to do in
Monteriggioni

Our most recommended things to do in Monteriggioni

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

1. 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, listed as UNESCO World Heritage Sites. 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

2. 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

3. 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 Siena: Chianti and Castles Tour with Wine Tastings

4. From Siena: Chianti and Castles Tour with Wine Tastings

Immerse yourself in picturesque Tuscan scenery on a sightseeing day trip from Siena to the region of Chianti. Visit the Castellina in Chianti before partaking in a wine tasting experience at a wine estate.   Board a spacious and climate controlled van in a centrally-located meeting point in Siena. Admire the Italian countryside on the ride as you pass thorugh pristine landscapes that have been cradling the Chianti vineyards for centuries. Discover a harmony of colors that can only be found in the hills of this region. Delight your senses as you dive into the sounds, scents, and flavors of this land will capture your senses through this unique experience.  Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Continues to a charming wine estate.  Indulge in a wine tasting paired with typical Tuscan food. View the beautiful ruby-red color and the characteristic bouquet with scents of violet are the special to Chianti wine. Savor this blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second optional wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

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 an optional 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

6. 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

7. 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.

Florence: 24-Hour Noleggio Vespa, Scooter & Moped

8. Florence: 24-Hour Noleggio Vespa, Scooter & Moped

Enjoy an amazing trip around Tuscany, Florence, Siena and the Chianti area. Discover all most famous sights of Florence such as Piazzale Michelangelo, Fiesole, the Duomo, international museums, David and the fashion streets. Then, head to the countryside area, Chianti and Siena, where you will be introduced to delicious foods like cheeses, Florentine steak and the best wines of Italy. Along the way, you'll be able to capture colorful, pristine, natural and fantastic viewpoints with your camera. With your Vespa 125, you will not be obliged to eat near your hotel, but can go to the best restaurants with the best reviews without effort or spend 40 EUR for a short trip in a taxi. This service is not like the usual tourist tour but an amazing adventure through the real Tuscany and Florence.

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 Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine

10. From Siena: Chianti Countryside E-Bike Tour w/ Lunch & Wine

Cycle through the lush Chianti scenery on a rewarding e-bike tour departing from Siena. Take in views of vineyards, olive groves, and picturesque villages as you ride. Visit an ancient fortress and stop by a local farm to enjoy lunch, seasonal products, and wine. Meet your guide for the day in front of the pharmacy next to the main entrance of Siena's train station. Familiarize yourself with the E-Bikes and equipment before heading out into the Chianti, one of the world’s most famous cycling areas! The assistance from the E-bikes makes biking in Tuscany accessible to all! Easily set the difficulty of your ride and decide whether you would like the bike to do most of the work, or do the workout yourself. The silent electric motor, allows you to enjoy the smells, sounds and tranquility of the Tuscan countryside. Finally begin your ride on secondary roads with limited traffic for a 20km long cycle. During the 3 hour ride, cross neat rows of vineyards, pretty olive groves, dense and shaded forests, and sleepy villages along the road. Immerse yourself in the traditional Chianti landscape with frequent stops throughout the morning to take in the views, breathe in the clean air and to stretch your legs. Visit a beautifully restored fortress dating back to the 13th century, cited by Dante in his Divine Comedy, an imposing Sienese bastion of defense against rival armies. Monteriggioni is now a fortified town where you can leisurely walk the alleys and squares to take in the medieval charm but also visit the church or local shops of crafts and products. Return to your E-bikes for a short ride to a local farm to sit down to a delicious lunch with local wine and extra virgin olive oil while learning about the local wines. Taste the extra virgin olive oil accompanied by platters of tasty local and seasonal products and traditional wines. After lunch, pedal the last leg back to Siena train station after a rewarding, up close experience with nature and wine, some of the best that Tuscany has to offer!

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What people are saying about Monteriggioni

Overall rating

4.4
(6,022 reviews)

Alissandri was awesome! thanks for the great tour, highly recommended for new visitors wanting to tour Tuscany. loved the experience and I will definitely use their tours for other Italy adventures. thank you Michel, Alissandri, and Jay for the wonderful hospitality and guidance. Go for this!

Great trip, well organised, and our guide was very knowledgeable, giving just enough bite-sized fun facts for us to get to know the cities with context. Not too rushed. We could have had a little more time at the first stop, but I understand they were necessary for the long car journeys.

Patricia and Alexandra were very friendly, the group was large but everything was orderly and they had a lot of experience. The places were spectacular. In the vineyard the best was the balsamic, it is a unique experience. The best ice cream is consumed in San Gimignano

We liked visiting Pisa and San Geminniano but we didn't like that we had little time in both places, we felt that we needed more time to explore the

Great experience with our amazing hosts. The trip was planned and not rushed at all , beautiful locations and absolutely great wine tasting session.