Chianti and San Gimignano – 2 Wineries with Pairing Lunch

This experience made our article of Our 15 Favorite Siena Lunch Experiences.

A Day in Tuscany: Wineries, Medieval Towns, and Gourmet Food

If you’re dreaming of a perfect Tuscany day trip, this tour from Siena hits all the right notes. For around $324 per person, you get approximately eight hours of exploring the Chianti wine region, visiting two carefully selected wineries, tasting a variety of top Chianti Classico and white wines, and enjoying a gourmet Tuscan lunch. Plus, you’ll get a chance to stroll through San Gimignano, one of Tuscany’s most iconic medieval towns, or visit the charming Monteriggioni.

Two things we especially love: First, the guided wine tastings at two different estates—each with its own unique character—offer real insight into Tuscan winemaking. Second, the lunch with wine pairing in San Gimignano is both generous and sophisticated, giving you a true taste of regional cuisine.

A potential consideration is the winding, sometimes narrow roads between stops; if you’re prone to motion sickness, bring some remedies. This tour suits travelers who appreciate authentic wine experiences, love history and scenery, and prefer not to rent a car. It’s especially ideal for those who want a well-organized, informative day that combines wine, culture, and crisp Tuscan air.

Key Points

• All-in-one experience including two winery visits, gourmet lunch, and medieval town explorations
• Guided by knowledgeable English-speaking drivers who share insights about Tuscany’s culture and wines
• Convenient pickup and drop-off from Siena, Florence, or the Chianti region
• Intimate group size (max 8), ensuring personalized attention and a relaxed atmosphere
• Authentic visits to different types of wineries, from historic to boutique family-run estates
• Flexible itinerary with stops in San Gimignano or Monteriggioni, balancing wine with cultural sightseeing

Why This Tour Stands Out

Tuscany’s allure is in its beautiful landscapes, historic towns, and, of course, its wine. This tour captures that perfectly by combining a scenic drive with engaging visits to two distinct wineries. The first stop near Monteriggioni offers a glimpse into Chianti’s historic roots, with a knowledgeable guide sharing stories that bring the land to life. The second visit, in San Gimignano, feels like stepping back in time—its medieval towers and cobblestone streets are postcard-perfect.

What sets this experience apart is the way it balances organized visits with free time—you’ll have enough time in San Gimignano or Monteriggioni to wander, enjoy a gelato, or snap photos of those iconic medieval towers.

The guided tastings are a highlight. Guests have raved about the expertise and friendliness of the guides, like Camilla and Stefan, who make the wine stories engaging. Many reviewers mention how much they appreciated the variety of wines, including Chianti, Vernaccia, sparkling Sangiovese, and Vin Santo at lunch, which helps you learn about regional specialties beyond just red wine.

The Itinerary in Detail

Monteriggioni: A Medieval Fortress

Starting near Monteriggioni, you’ll visit a historic Chianti Classico winery. This area is famed for its medieval walls and towers, which create a fairy-tale setting. The winery, often small and family-run, provides a personalized tasting experience. Reviewers love this first stop for its peaceful setting and excellent wines, with one describing the winery as beautiful and historic.

Scenic Drive Along Chiantigiana

Your driver-guide, typically an English speaker, will share stories about the region’s geography, wine-making, and history as you enjoy a comfortable ride through the rolling hills. This part of the tour is often praised for the spectacular scenery and the informative commentary that enriches your understanding of Tuscany’s landscape.

San Gimignano: A Medieval Marvel

Next, you’ll stroll through San Gimignano’s narrow streets, with its famous towers and well-preserved architecture. This UNESCO-listed town feels like a living museum, and many visitors mention how much they loved the free time to explore, visit local shops, or simply soak in the atmosphere.

Gourmet Lunch & Wine Pairing in San Gimignano

The highlight for many is the lunch in a renowned winery. Here, you’ll taste a selection of Tuscan specialties such as local cheeses, cured meats, fresh pasta, and regional desserts. They pair these with both red and white wines, including Vernaccia, Sparkling Sangiovese, and Vin Santo. Reviewers consistently mention that the lunch exceeded expectations with outstanding food and wine in a welcoming setting.

End of Day: Return to Your Hotel

After the last tasting and a leisurely stop at San Gimignano or Monteriggioni, your driver will return you to your hotel or nearby location. The small group size makes for a relaxed, intimate experience—you won’t feel lost in a crowd, and your guide can answer all your questions.

Transportation and Group Size

The tour provides an air-conditioned vehicle, which is appreciated on hot days or winding roads. Pickups and drop-offs from Siena, Florence, or the Chianti area add to the convenience, especially if you’re staying in one of these places.

With a maximum of 8 travelers, the experience maintains a personal touch. Many reviews highlight how this small-group format fosters friendly conversations and a more tailored experience, unlike larger bus tours that can feel rushed or impersonal.

Price Analysis and Value

At $323.94 per person, this tour might seem like a splurge, but considering the two winery tours, lunch, transportation, and guided commentary, it offers excellent value. Many reviews emphasize that the quality of the wineries and food makes it worthwhile, especially for those who want a comprehensive, authentic taste of Tuscany without the hassle of self-driving or booking multiple separate experiences.

The included tastings and lunch with wine pairings give you a chance to try a wide range of wines, making your day both educational and delicious. Plus, the small group size ensures you’re not just another face in a crowd, but a welcomed guest at each stop.

Authentic Experiences According to Travelers

Reviewers consistently praise the guides’ knowledge and friendliness, often mentioning how guides like Stefan and Camilla made the day special by sharing stories and answering questions.

The scenery’s beauty gets almost universal praise—rolling vineyards, medieval towers, and scenic drives—making every moment picture-worthy.

Many travelers highlight the variety of wineries—from historic estates with tombs dating back to the 6th century BC to boutique family-run farms—giving a real sense of regional diversity.

The lunch experience stands out as a real highlight. Guests describe it as “more than expected,” with delicious food and excellent wine pairings that showcase Tuscan culinary traditions.

Who Will Love This Tour?

This experience is best suited for wine enthusiasts who want to deepen their understanding of Chianti wines and enjoy Tuscany’s landscape. It’s ideal for those who prefer small-group tours with personalized attention rather than large bus setups.

If you’re someone who appreciates authentic, off-the-beaten-path wineries, this tour checks that box. It’s perfect if you want some cultural sightseeing as well, with stops in medieval towns that look like they’ve frozen in time.

Travelers who value delicious food and educational tastings will find it especially rewarding. However, if you’re prone to winding roads or seeking a more relaxed pace, that’s worth considering.

FAQ

What is included in the tour?
The tour includes visits to two wineries with guided tastings, a gourmet lunch with wine pairing, pick-up and drop-off from your hotel or nearby, bottled water, and an English-speaking driver-guide.

How long does the tour last?
It is approximately eight hours from start to finish, giving you plenty of time at each stop as well as sightseeing in San Gimignano or Monteriggioni.

Can I customize the stops?
The itinerary is fixed, but the small group size and knowledgeable guides often lead to a flexible and engaging experience.

Is this suitable for all ages?
Most travelers can participate. However, those sensitive to winding roads or with mobility issues should note the scenic drives and cobblestone streets.

What wines will I taste?
You’ll sample Chianti Classico, Vernaccia, Sparkling Sangiovese, Vin Santo, and other regional varietals, depending on the winery and season.

What is the dress code?
Casual but tidy is fine—think comfortable shoes for walking, especially in towns like San Gimignano.

How does the transportation work?
You’ll ride in an air-conditioned vehicle, with pickup and drop-off arranged from specified locations, ensuring convenience.

Are the wineries family-owned?
Many of the wineries visited are small, often family-run estates, providing a more authentic and intimate experience.

What do reviews say about the guides?
Guests consistently praise the guides’ knowledge, friendliness, and ability to make the day enjoyable and informative.

Final Thoughts

This Chianti and San Gimignano day tour offers a rich taste of Tuscany’s wine, history, and scenery in a well-organized, intimate setting. With visits to historic wineries, a delicious lunch, and free time in picturesque towns, it truly captures the essence of the region.

It’s a highly recommended choice for wine lovers, history buffs, or anyone wanting a relaxed, behind-the-scenes look at Tuscany’s iconic landscape. The combination of guided insight and free exploration means you’ll leave with both a fuller glass and a fuller heart.

If you value authentic experiences, expert guides, and the convenience of small-group touring, this tour is worth considering for your Tuscan adventure.