This full-day tour from Florence offers travelers a captivating exploration of Tuscany’s medieval gems and renowned winemaking traditions. Visitors will discover the historic charm of Siena, with its iconic cathedral and lively piazza, before delving into the rolling hills of the Chianti region. A visit to a family-run farm includes a gourmet Tuscan lunch and guided wine tastings, providing an authentic taste of the local lifestyle. The tour culminates in the UNESCO-listed town of San Gimignano, renowned for its impressive medieval towers and enchanting streets. For those seeking to enjoy the rich cultural and culinary heritage of Tuscany, this tour promises an unforgettable experience.
This experience made our list of the 20 Best Wine Tours In Florence.
Key Points

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Full-day small-group tour from Florence to explore the medieval towns of Siena, Chianti region, and San Gimignano, with guided visits and wine tastings.
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Discover the architectural wonders of Siena, including the iconic Cathedral and Piazza del Campo, and learn about Tuscany’s medieval history.
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Experience the Chianti winemaking traditions with a visit to a family-run farm, gourmet lunch, and guided tasting of renowned Chianti wines.
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Indulge in the charming medieval atmosphere of San Gimignano, known for its impressive network of towers and famous saffron-infused gelato.
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Enjoy a seamless and immersive tour experience led by an expert English-speaking guide and professional driver throughout the day.
Overview of the Tour
This full-day tour takes visitors from Florence to the picturesque Tuscan countryside, providing a small-group experience limited to 14 people or fewer.
Guests will explore the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race.
Next, they’ll visit a family-run farm in the Chianti region for a gourmet lunch and wine tastings.
The tour then continues to the UNESCO-listed storybook village of San Gimignano, where an expertly guided walking tour brings the town’s history to life.
Throughout the day, an expert English-speaking guide and professional driver ensure a seamless and enjoyable experience.
You can also read our reviews of more wine tours in Florence
Exploring the Medieval Siena

Stepping into the captivating medieval town of Siena, visitors are immediately struck by its remarkably well-preserved architecture and vibrant piazzas.
The centerpiece of the town is the iconic Siena Cathedral, a stunning Gothic masterpiece adorned with intricate marble and mosaic details.
Wandering through the winding streets, one can’t help but marvel at the striking 14th-century buildings that line the town’s main square, Piazza del Campo.
This lively plaza is also the site of the famous Palio horse race, a centuries-old tradition that draws crowds from around the world.
With its rich history and enchanting atmosphere, Siena offers a glimpse into the heart of Tuscany’s medieval past.
Discovering Chianti Region

The Chianti region, nestled in the heart of Tuscany, beckons visitors with its rolling hills, picturesque vineyards, and family-owned wineries.
Guests on this tour have the opportunity to explore the rich winemaking traditions of this renowned area, savoring the flavors of its world-renowned Chianti wines.
The tour includes a visit to a family-run farm, where travelers will indulge in a gourmet lunch paired with a guided wine tasting. This intimate experience allows guests to learn about the production process and appreciate the nuances of the region’s terroir.
With knowledgeable experts leading the way, the Chianti portion of the tour promises to be a highlight, offering a taste of the authentic Tuscan lifestyle.
Lunch and Wine Tasting

Guests will savor a gourmet lunch and indulge in expert-led wine tastings at a family-run farm in the heart of the Chianti region.
They’ll enjoy a delicious spread of local specialties, including fresh-baked bread, cured meats, and regional cheeses.
The farm’s passionate vintners will guide them through a tasting of their renowned Chianti wines, sharing insights into the region’s winemaking traditions.
Visitors will have the opportunity to purchase bottles to take home, ensuring they can relive the flavors of Tuscany long after the tour has ended.
This immersive culinary experience provides a true taste of the Chianti countryside.
Visiting San Gimignano

After savoring the flavors of Chianti, the tour heads to the UNESCO-listed town of San Gimignano, known for its impressive medieval towers that dot the skyline. Visitors explore the charming streets and squares, marveling at the remarkably preserved Gothic architecture that transports them back in time. The guide provides insights into the town’s history and points out notable landmarks, ensuring guests gain a deeper appreciation for this storybook Tuscan gem.
The highlights of visiting San Gimignano include:
- Admiring the 14 remaining medieval towers that were once part of a network of 72 towers.
- Exploring the quaint Piazza del Duomo and its striking Cathedral.
- Indulging in the town’s famous saffron-infused gelato.
- Shopping for local handicrafts and artisanal products in the charming shops.
You can also read our reviews of more tours and experiences in Florence
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- Siena and San Gimignano: Small-Group Tour With Lunch From Florence
- Chianti Wineries Tour With Tuscan Lunch and San Gimignano
- Essence of Chianti Small Group Tour With Lunch and Tastings From Florence
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Expert English-speaking Guide

An expert English-speaking guide leads the tour, providing invaluable insights and commentary throughout the journey. Their extensive knowledge of the Tuscan region enhances the experience, bringing the history, culture, and traditions of each destination to life.
Whether it’s explaining the intricate architecture of Siena’s magnificent cathedral or sharing local legends about San Gimignano’s iconic towers, the guide ensures guests leave with a deeper appreciation for the area. Their fluency in English makes it easy for all participants to engage and ask questions, fostering a more personalized and enriching experience.
With the guide’s expertise, guests can sit back, relax, and fully enjoy the beauty of the Tuscan countryside.
Transportation and Accessibility

The tour provides air-conditioned transport to whisk guests comfortably between the picturesque Tuscan destinations.
While the walking tours in Siena and San Gimignano require a moderate level of mobility, the tour can’t accommodate wheelchairs or strollers.
Guests with any special needs should contact the tour provider after booking to ensure the experience meets their requirements.
The tour highlights include:
- Air-conditioned transportation for a comfortable journey
- Professional driver to navigate the scenic Tuscan roads
- Walking tours in Siena and San Gimignano that require moderate mobility
- Inability to accommodate wheelchairs or strollers on the tour
Booking and Confirmation

Guests receive confirmation of their booking at the time of purchase. The tour provider requires contact after booking for those with dietary restrictions to accommodate their needs. Infant seats are available upon request, and the tour complies with local government regulations.
Unfortunately, the tour can’t accommodate those with mobility limitations, wheelchairs, or strollers. Guests should be prepared for walking during the guided tours of Siena and San Gimignano.
The small-group size is limited to 14 people or fewer, ensuring a more intimate and personalized experience. With an expert English-speaking guide and designated professional driver, guests can look forward to a seamless and enjoyable day exploring the picturesque Tuscan countryside.
Frequently Asked Questions
Can I Request a Specific Dietary Preference?
Yes, travelers with dietary restrictions can contact the tour provider after booking to request a specific meal preference. The provider will accommodate these requests to the best of their ability.
Is It Possible to Join the Tour at a Different Location?
Yes, it’s possible to join the tour at a different location. Travelers should contact the tour provider after booking to coordinate an alternate meeting point. The tour provider will accommodate requests within reason.
What Happens if I Am Late for the Meeting Point?
If you’re late to the meeting point, the tour won’t wait for you. You’ll miss the transportation and guided portions of the tour. Contact the tour provider to see if you can join the group at another location, but this isn’t guaranteed.
Can I Bring My Own Wine on the Tour?
No, you cannot bring your own wine on the tour. The tour includes wine tastings at a family-run farm, so bringing your own wine is not permitted. The tour provider’s policy is to provide the wine tastings as part of the tour experience.
Is It Possible to Extend the Tour Duration?
The tour duration can be extended, but it would require additional arrangements and costs. Customers should contact the tour provider after booking to inquire about extending the tour and get a quote for the additional time and services.
Recap
This Tuscan day trip from Florence offers a captivating blend of medieval history, scenic countryside, and culinary delights.
Visitors will explore the charming towns of Siena and San Gimignano, indulge in a gourmet Tuscan lunch and wine tasting, and enjoy the region’s rich winemaking traditions.
With an expert guide and comfortable transportation, it’s an excellent way to discover the essence of Tuscany in a single day.
More Lunch Experiences in Florence
- “Good Morning Chianti Classico” – Tour in 2 wineries with lunch
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- PRIVATE TOUR: Pisa & Chianti in one day with Lunch and Wine tasting Experience
- Heart of Chianti Classico – 2 Wineries Lunch included – Chianti Wine Tour
- San Gimignano with lunch and wine tasting on a local winery
- Florence: Brunello Wine Tour with Lunch at the Winery
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