Florence: Wineries, Tastings, Lunch & San Gimignano Day Trip

Planning a day out of Florence that combines wine, history, and stunning scenery? This small-group tour offers just that — giving you a flavor of Tuscany that’s both relaxed and immersive. From visiting organic wineries to strolling through medieval streets, it’s a trip that many travelers find balances great value with memorable experiences.

What we really appreciate about this experience is its focus on authentic, family-run wineries and the chance to learn about Chianti wines in a setting that’s intimate rather than commercial. Plus, the stop at San Gimignano — with its breathtaking skyline and renowned gelato — is a highlight for many. That said, one thing to keep in mind is that the lunch is described as “light,” which might not satisfy someone looking for a full meal. Still, the overall vibe and expert guides make this tour ideal for those who want to truly savor Tuscany in a day.

This trip is perfect if you’re after a small, personalized experience with knowledgeable guides, excellent wine tasting, and a scenic visit to a medieval hilltop town. It’s well-suited for anyone looking to deepen their appreciation of Tuscan wine culture, enjoy beautiful countryside views, and explore a UNESCO-listed town without the hassle of self-driving.

Key Points

• Intimate small group size (limited to 8 participants) ensures a relaxed, personalized experience.
• Authentic visits to organic, family-run wineries provide insight into traditional wine and olive oil making.
• Expert guides make the experience engaging, informative, and fun, often with positive reviews about their personality and knowledge.
• Taste a range of Chianti wines, including some aged bottles and special olive oils, that many find excellent quality and good value.
• Visit San Gimignano, famous for its medieval towers and gelato, with plenty of time to explore.
• Includes a “light” Tuscan lunch, paired with wines — a good option for a light snack rather than a full meal.
• Stops at Piazzale Michelangelo at the end offer a panoramic view of Florence, perfect for winding down.
• Flexible booking policies with free cancellation up to 24 hours in advance add peace of mind.

You can check availability for your dates here:

The Breakdown: What to Expect

Meeting Point & Transport

You’ll meet just outside cafe Gamberini, a quick 5-minute walk from Florence’s main train station. This makes it easy to find without fuss, especially after arriving in Florence. The tour includes transportation in a comfortable vehicle, which takes you through picturesque Tuscan landscapes. Given the limited group size, the journey feels cozy, and your guide is available to share insights along the way.

The First Winery Experience

The day kicks off with a visit to a boutique organic farm located in the heart of Chianti. Here, you’ll get a behind-the-scenes look at how Chianti wines are made — from vineyard to cellar — and learn about the process of aging and blending. You’ll also discover how extra virgin olive oil is produced, which adds an extra layer to understanding traditional Tuscan food.

Based on reviews, this first stop is often praised for being informative and welcoming. One guest shared, “Francesco, the owner, had a great spread and the wine was fantastic. You could tell he was passionate about his craft.” Many visitors appreciate the personalized service and the opportunity to buy wines and oils at a good price, which makes the experience even more worthwhile.

Wine Tasting & Olive Oil

The tasting here is more than just sipping — it’s about understanding the characteristics of Chianti wines, and many reviewers mention that the wines exceeded expectations. You’ll sample a variety of wines and have the chance to purchase some at a reasonable price, which is always a perk. The guide’s knowledge really shines here, making the tasting engaging and educational. Multiple reviews mention the quality of the wines as a highlight.

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Exploring San Gimignano

Next, you’ll head to San Gimignano, a UNESCO-listed medieval town famous for its towers and charming streets. You’ll have a good amount of free time to wander, shop, or simply take in the views. Many visitors rave about the gelato at Gelateria Dondoli, which has won global awards. One review called it “the best gelato in the world,” and it’s easy to see why — creamy, inventive flavors, and a lively atmosphere.

The town’s atmosphere is both historic and lively, making it a perfect photo op and a chance to soak in Tuscan architecture. If you’re into history, architecture, or just want some postcard-worthy shots, this stop hits the mark.

The Second Winery & Light Lunch

Your next stop is another local winery, where you’ll enjoy a light Tuscan lunch paired with a curated tasting of Chianti wines. The meal is described as a simple yet delicious selection of local dishes, ideal for a quick refresh. Reviews mention the delicious food and beautiful outdoor seating with views of the vineyards.

This part of the day is more relaxed, giving you a chance to chat with your guide and fellow travelers. You’ll also get to taste an impressive 30-year-old balsamic vinegar and truffle olive oil, elevating the experience beyond just wine tasting. Many reviews highlight the quality of these products and appreciate the opportunity to sample such authentic flavors.

Final Stop: Piazzale Michelangelo

On the way back to Florence, you’ll make a quick stop at Piazzale Michelangelo. The panoramic view of Florence is often described as breathtaking and a perfect way to conclude the day. Visitors have shared that it’s one of Florence’s most romantic spots, and many love taking photos here.

Duration & Group Size

The entire tour lasts about 8 hours, making it a full but manageable day. Being a small group means fewer crowds and more personal interaction, which many reviews confirm enhances the experience. Guides are multilingual, with options in English, Italian, and Spanish, and generally received praise for their friendliness and knowledge.

Price & Value

Considering the visits to two wineries, a guided tasting, a light lunch, and a scenic town tour, many find this tour to be excellent value. The reviews suggest that the quality of the wineries, guides, and scenery far outweigh the cost, especially given the personalized approach.

Real Experiences from Travelers

Many reviews emphasize how much they enjoyed the knowledge and friendliness of the guides. For example, Nicoletta from the U.S. said, “Our driver Daniel made our tour most pleasurable,” highlighting how guides can make or break the experience.

Others appreciated the variety of wineries, noting that the first was very informative, while the second offered a different vibe with a lovely outdoor setting. One guest shared, “The first winery was fantastic — Francesco was passionate — but the second was more laid-back, which was nice after the first.”

The scenery also features prominently in reviews, with travelers mentioning the stunning landscapes and picturesque towns. The tasting quality consistently earns praise, with many noting the wines and oils they tasted were exceptional and a good value for the price.

Who Should Consider This Tour?

This experience is especially suited for wine lovers and those wanting a personalized, small-group vibe. If you’re interested in learning about Chianti wines and olive oils from passionate producers, you’ll find the visits meaningful. It’s also great for history and architecture buffs eager to explore San Gimignano’s medieval streets without the hassle of navigating on your own.

While the lunch is light, it’s perfect for those who prefer a quick, quality meal paired with wine rather than a large banquet. It’s not ideal if you’re looking for a full sit-down dinner or have specific dietary restrictions, as the meal is more of a tasting experience.

Overall, if you’re after a balanced, engaging day that combines tasting, sightseeing, and learning, this tour hits the spot.

FAQs

Is this tour suitable for children or families?
While not specifically marketed as a family tour, children who enjoy wine tasting and exploring towns like San Gimignano could find it enjoyable. The tour is mainly aimed at adults, but it’s not restricted.

How long are the winery visits?
Most of the visits include a guided tour and tasting, with the first winery being quite informative and the second more relaxed, combined with a light lunch.

What is included in the light lunch?
The lunch features simple, authentic Tuscan dishes, paired with wine, balsamic vinegar, and olive oil tastings. It’s designed as a tasting rather than a full meal.

Can I buy wine and oils at the wineries?
Yes, many guests mention they could purchase quality wines and oils at favorable prices directly from the wineries.

Is transportation comfortable?
Yes, the tour includes transportation in a comfortable vehicle, making the journey through scenic Tuscany pleasant.

How flexible is the booking?
You can reserve now and pay later, with free cancellation up to 24 hours before the tour.

What is the group size?
Limited to 8 participants, ensuring a more intimate experience.

Are guides available in multiple languages?
Yes, guides speak English, Italian, and Spanish, and are often praised for their friendliness and depth of knowledge.

Final Thoughts

This small-group tour from Florence offers an authentic taste of Tuscany’s wine and medieval charm. It’s perfect if you want a personalized experience with knowledgeable guides, stunning scenery, and high-quality tastings. Reviewers consistently highlight the passion of the winemakers, the beauty of the countryside, and the deliciousness of the food.

If you’re after a well-rounded, engaging day that combines wine, history, and scenic views, this trip will serve you well. Just keep in mind that the lunch is light, so plan your expectations accordingly. Overall, it’s a fantastic way to experience a slice of Tuscany without the hassle of organizing everything yourself.

Whether you’re a seasoned wine enthusiast or just looking to see more of Tuscany’s countryside, this tour balances fun, learning, and relaxation nicely. Highly recommended for those who want a genuine, personable experience out in the rolling hills of Chianti.

You can check availability for your dates here: