San Gimignano Monteriggioni Tuscany Chianti Wine Tasting Fullday from Florence

San Gimignano, IT
San Gimignano, IT
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Embark on a journey through the enchanting landscapes of Tuscany with this unforgettable tour. Explore the medieval gems of San Gimignano and Monteriggioni, where time seems to stand still amidst towering ancient walls and impressive architecture. Travel along the picturesque Chianti Road, surrounded by rolling hills and vineyards, and indulge in a delightful wine tasting experience. Immerse yourself in the rich history and captivating beauty of this renowned region, all while being guided by expert professional English-speaking drivers. Choose between a private or shared tour option, and rest assured that your safety and comfort are a top priority with fully-insured air-conditioned vehicles. Upgrade your experience with a licensed local guide, who will unveil the secrets and stories of each destination. Take the plunge and book this worry-free and captivating journey through the heart of Tuscany.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 12 hours
  • Suitable for 1-8 Participants
  • Private Tour
  • Guided Experience
  • Explore the picturesque town of San Gimignano
  • Experience the beautiful Chianti countryside
  • Enjoy a wine tasting in the Tuscany countryside
  • Discover the medieval walled town of Monteriggioni
  • Experience the landscapes and small towns of Tuscany
  • Air-conditioned, fully insured and licensed legal vehicle with professional English-speaking Driver
  • Hotel pickup and dropoff
  • Dedicated Local Licensed Expert Tour Guide (upgradable in Private option)
  • Wine Tasting
  • Lunch, Food and drinks
  • Tipping is not included in our service fees, it is never mandatory although it is always appreciated

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More about this experience


Experience the magic of Tuscany with the San Gimignano Monteriggioni Tuscany Chianti Wine Tasting Fullday Tour from Florence. This tour will take you on a journey through the picturesque landscapes and artistic small towns that define the beauty of this region. Immerse yourself in the history and charm of Italy as you explore the medieval hilltop town of San Gimignano, known for its breathtaking towers and impressive architecture. Traverse the rolling hills of the Chianti countryside, where endless vineyards and green valleys await. Discover Monteriggioni, a fortified town with a rich history and stunning views.

What to expect?

During this tour, you can anticipate a memorable day filled with breathtaking sights and enriching experiences. Marvel at the well-preserved medieval towers and encircling walls of San Gimignano, immersing yourself in its unique atmosphere. Journey through the Chianti region, known for its picturesque landscapes and delicious wines. Engage in a wine tasting experience, savouring the flavors of Tuscany's renowned wines. Explore Monteriggioni and uncover its medieval charm and fascinating history.

Who is this for?

This tour is ideal for anyone seeking a captivating exploration of Tuscany's treasures. Whether you're a history enthusiast, a wine lover, or simply someone who appreciates the beauty of unique landscapes, this experience is perfect for you. It welcomes individuals, couples, families, and groups of friends alike, offering something for everyone. Discover the wonders of Tuscany together and create cherished memories.

Why book this?

Embark on this remarkable tour to discover the true essence of Tuscany. The San Gimignano Monteriggioni Tuscany Chianti Wine Tasting Fullday Tour presents an opportunity to witness the captivating beauty of San Gimignano's towers, immerse yourself in the rolling hills of Chianti, and delve into the history of Monteriggioni's fortified walls. With expert English-speaking drivers and optional licensed local guides, you will benefit from a worry-free and safe experience. Travel in comfortable, air-conditioned vehicles as you navigate through picturesque landscapes. This enchanting journey promises to be a highlight of your trip to Italy.

Good to know

As you embark on the San Gimignano Monteriggioni Tuscany Chianti Wine Tasting Fullday Tour, be prepared for a duration of approximately 720 minutes. The itinerary includes visits to San Gimignano, Chianti Road, and Monteriggioni, with specific durations for each destination. Marvel at the architecture of San Gimignano for 120 minutes, indulge in a wine tasting experience along the Chianti Road for 60 minutes, and explore the medieval walls of Monteriggioni for another 60 minutes. This tour offers a comprehensive experience of the region's highlights, giving you a taste of its rich history and breathtaking landscapes.


Customers who have embarked on this tour have been captivated by the beauty and charm of Tuscany. They have praised the knowledgeable and friendly drivers, who have provided insightful commentary and made the journey enjoyable. The wine tasting experience in the Chianti countryside has been a particular highlight, allowing travelers to savor the flavors of the region and enhance their visit. The well-preserved medieval towns of San Gimignano and Monteriggioni have left visitors in awe, offering a glimpse into Italy's fascinating history. Overall, individuals have expressed their satisfaction and recommended this tour as a must-do when visiting Florence and Tuscany.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

San Gimignano

San Gimignano is one of Tuscany’s prettiest and most famous small medieval hilltop towns. With a name that translates as the ‘Town of Fine Towers,’ it’s best known for its well-preserved medieval towers and encircling walls, which give it an unmistakable skyline. Inside the walls, its impressive buildings include notable examples of Romanesque and Gothic architecture.

Chianti Road

Travel through the Chianti region. This area of Tuscany boasts of endless rolling hills covered with grain or sunflowers, a rich green valley with vineyards. It is no wonder that this territory is protected as a World Heritage Site by UNESCO like Castellina. The quaint Etruscan village is home to a fortress that dates back to the 15th century. Wine Tasting included.


Monteriggioni is a medieval walled town, located on a natural hillock, built in 1214–19. During the conflicts between Siena and Florence in the Middle Ages, the city was strategically placed as a defensive fortification. It also withstood many attacks from both the Florentines and the forces of the Bishop of Volterra.

2024-05-18 10:01