Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

Traveling through Tuscany without tasting its famous wines and wandering its charming towns leaves a lot on the table. This full-day tour from Florence offers a solid introduction to the region’s viticulture, scenery, and small-town allure. Although it’s a structured experience, it balances guided tastings with free time, making it adaptable to different travelers’ pace.

What we love about this tour is the chance to sample up to 7 different wines across two distinctive wineries—one larger and more commercial, the other intimate and family-run. Both stops give insight into different approaches to winemaking, and the tasting sessions include more than just wine: extra-virgin olive oil, balsamic vinegar, and local delicacies truly enhance the experience. And of course, the visit to San Gimignano is a highlight, offering gorgeous views and a chance to browse its picturesque streets.

One thing to keep in mind is the timing in San Gimignano—with just about 90 minutes, you’ll need to prioritize what to see and do. For those craving a more leisurely pace or additional time in the town, this could feel a little rushed. However, for most, the balance of tastings and sightseeing hits the sweet spot.

This tour suits wine lovers, history enthusiasts, and those looking for an authentic taste of Tuscany without fuss or long drives. It’s perfect if you want a well-organized day that packs in flavor, scenery, and culture.

Key Points

• Two distinct wineries provide variety in wine styles and atmospheres
• Tasting up to 7 wines, including Chianti Classico, Super Tuscan, and Vernaccia
• Professional wine tasting lessons help develop your palate
• Includes olive oil and balsamic vinegar tastings
• Time in San Gimignano allows a quick but immersive visit to this iconic town
• Comfortable transportation with a small group creates a relaxed environment

You can check availability for your dates here:

An In-Depth Look at the Experience

Starting Point and Transportation

The day begins at the Church of San Giovanni Battista della Calza, conveniently located near “Porta Romana” in Florence. The guide in purple T-shirt makes it easy to spot. For those arriving from the train station, options include walking, bus, or taxi—just make sure you’re on time to start the day smoothly. The coach ride to the Tuscan hills lasts about an hour, giving you your first glimpses of the rolling vineyards and cypress-lined roads.

First Winery: A Larger, Luxury Experience

The first stop is at a luxury winery with a reputation for quality and efficiency. Here, you’ll try four different wines, including the famed Chianti Classico with its characteristic black rooster label, along with some Super Tuscan wines—a category that’s often richer and more complex. The tasting includes a 30-year-old balsamic vinegar and truffle extra virgin olive oil, adding layers of flavor and craftsmanship to the experience.

Guests consistently praise the guides’ ability to explain the wines and production processes clearly, turning each tasting into a mini-lesson. One reviewer noted, “We developed our taste buds with a professional wine producer,” highlighting the educational aspect. The atmosphere is lively, with music and a charismatic host, ensuring everyone feels comfortable.

Second Winery: A Family-Run Gem

Next, the group moves to a smaller, family-run winery facing the iconic towers of San Gimignano. Here, the focus is on Vernaccia white wine and Chianti Colli Senesi D.O.C.G., which you’ll taste alongside local oils and products for sale. The intimate setting allows more personalized interactions with the winemakers, who share their secrets of tradition and craft.

Reviewers often mention how this smaller winery’s stunning views of San Gimignano make the tasting even more memorable. One reviewer shared, “The view of the towers in the background was incredible,” emphasizing that this stop offers both delicious wine and picture-perfect scenery.

More Great Tours Nearby

Exploring San Gimignano

The free 1.5-hour window in San Gimignano is a highlight for many. With its medieval towers and narrow streets, the town exudes charm. You can wander at your own pace, shop for souvenirs, or indulge in the world-champion gelato — a treat highly recommended by visitors. This brief visit, though tight, allows a taste of Tuscan history and ambiance without feeling rushed.

Return Journey

Departing around 3:45 PM, the group heads back to Florence, arriving roughly at 5 PM. This timing makes it feasible to include the tour in a full day of sightseeing without it feeling overly long. The coach ride offers reflection time, and many reviews mention how the experience exceeded expectations for value and enjoyment.

What Makes This Tour Stand Out?

Expert Guides and Personal Touches

Reviews consistently highlight the knowledgeable, friendly guides who make the day both educational and fun. One traveler said, “Alessandro was fun, very informative, and kept the group engaged,” while others appreciated the small group size for a more personal experience.

Quality Wine and Local Food

The emphasis on quality tastings — from Chianti to Vernaccia — ensures you’re sampling authentic and well-selected wines. Plus, the addition of balsamic vinegar and olive oil elevates the tasting experience, giving you a real sense of Tuscan culinary traditions.

Stunning Scenery and Town Charm

Both wineries are situated in beautiful settings with sweeping views of hills and vineyards, and San Gimignano’s towers are rightly famous. Visitors repeatedly mention how the scenery enhances the tasting and creates unforgettable memories.

Value for Money

Considering the transportation, expert guides, multiple tastings, and time in San Gimignano, many reviewers feel this tour offers excellent value. For a full day of entertainment, education, and scenery, the price is reasonable.

Practical Details and Tips

Duration and Timing

At about 7 hours, this is a full but manageable day trip. Starting around 9:45 AM and returning by 5 PM fits well into most travelers’ schedules. Do note that in summer, the group size is capped at 50, which helps keep the experience intimate.

Group Size

The tour offers a small group option, which many reviews say makes for a more relaxed and personalized experience. This can be especially helpful at wineries, where you can ask questions and interact more freely.

What to Bring

A passport or ID is needed, particularly for the wine tastings. Comfortable shoes are recommended for wandering San Gimignano’s cobbled streets.

Accessibility and Suitability

The tour isn’t suitable for pregnant women, wheelchair users, or children under 18, mainly due to the nature of tastings and walking involved. If you’re traveling solo, the small group size makes it easier to connect with others.

Other Considerations

If you’re planning to stay overnight in Siena, ask your guide about dropping you off there instead of Florence. That way, you can continue exploring without doubling back.

Authentic Experiences Highlighted by Travelers

Based on reviews, many visitors appreciated the knowledge and charisma of guides like Antonello and Lorenzo, who made the day lively and informative. The diversity of wineries—one large, one small—was appreciated for offering contrasting insights into Tuscan winemaking. Visitors also praise the stunning vineyard views, generous wine selections, and friendly hosts.

Some mentioned the short time in San Gimignano felt a bit rushed but still enough for a quick exploration and gelato. Several reviews noted that the quality of wines and the enthusiasm of guides made this trip memorable.

This Tuscany wine tour from Florence proves to be a solid choice for wine enthusiasts and culture seekers alike. The combination of two distinct wineries, offering both depth and variety, allows travelers to appreciate different sides of Tuscan winemaking. The inclusion of local products like olive oil and balsamic vinegar adds a flavorful dimension, and the visit to San Gimignano offers a perfect taste of Tuscan medieval charm.

The small group setting and knowledgeable guides ensure that the experience feels personal and engaging, making it easier to ask questions and connect. The scenic views and the opportunity to taste seven wines make this a satisfying and worthwhile day trip.

While the brief time in San Gimignano might be a drawback for those wanting a more leisurely stroll, most find that the balance of tastings, scenery, and free exploration hits the right note. If you’re looking for a well-organized, fun, and flavorful way to discover Tuscany’s wine country, this tour delivers impressive value.

This experience suits first-time visitors who want a comprehensive taste of Tuscany, as well as seasoned wine lovers eager to sample different styles in a stunning setting. It’s ideal for travelers seeking a guided, enjoyable, and authentic journey through Italy’s most famous wine region.

How long is the tour?
It lasts approximately 7 hours, from the meeting point in Florence to returning in the late afternoon.

Is transportation included?
Yes, the tour includes transportation by bus or van, with a comfortable ride through the Tuscan countryside.

Where does the tour start?
The meeting point is at the Church of San Giovanni Battista della Calza, near Porta Romana in Florence.

Is there enough time in San Gimignano?
You’ll have about 1.5 hours in San Gimignano, enough to explore briefly, shop, or enjoy gelato.

Can I buy wine and products during the tour?
Yes, at the second winery, you can purchase local wines, olive oils, and balsamic vinegars at favorable prices.

Is this tour suitable for children or pregnant women?
No, it’s not suitable for children under 18 or pregnant women, mainly due to wine tastings and walking.

What should I bring?
A passport or ID is necessary, and comfortable shoes are recommended for walking in San Gimignano.

Can I be dropped off in Siena instead of Florence?
Yes, if you are staying overnight in Siena, ask your guide about being dropped off there, saving travel time back to Florence.

In essence, this tour offers a taste of Tuscany’s finest wines, picturesque towns, and warm hospitality—all wrapped into a day designed to delight, inform, and inspire.

You can check availability for your dates here: