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

A Taste of Tuscany: Wineries, San Gimignano & More

This Florence-based tour offers a deep dive into Tuscany’s celebrated Chianti wine region. You’ll visit two family-run wineries, each with its own story and style, enjoy a typical Tuscan light lunch, and stroll through the enchanting medieval streets of San Gimignano. With a small group limited to just eight people, the experience feels intimate and personalized, giving you a chance to really connect with local producers and the scenery.

Two things I particularly love about this experience are the guided tastings that reveal the secrets behind Chianti’s famous wines and the opportunity to buy some of the best Tuscan wines at reasonable prices. Plus, the visit to San Gimignano, with its iconic towers and the chance to savor the world champion gelato at Gelateria Dondoli, makes this trip stand out.

A potential consideration is the full day’s schedule—with visits, tastings, and sightseeing packed into eight hours, it’s a busy day. You’ll want to wear comfortable shoes and be prepared for some walking and standing, especially in town and winery settings. Also, the lunch at the second winery might not satisfy everyone’s palate equally, according to reviews, so if food is a priority, plan accordingly.

Key Points / Takeaways

• Small Group Size: Limited to 8 participants, making it easier to ask questions and enjoy a more personal experience.
• Expert Guides: Guides like Christian and Daniel are praised for their friendliness and knowledge, adding a lot of value.
• Authentic Wineries: Visits to family-run, organic farms provide genuine insights into traditional wine and olive oil production.
• San Gimignano: This medieval hilltop town with its famous towers is a highlight, along with the chance to taste award-winning gelato.
• Tasting and Shopping: You’ll sample Chianti wines, balsamic vinegar aged up to 30 years, and truffle olive oil—and have the opportunity to purchase them at good prices.
• Price and Value: At around $215 per person, this tour offers excellent value, combining tastings, sightseeing, and a meal in one well-organized package.

Entering the World of Tuscan Vineyards

The tour’s core is a visit to a small organic farm in Chianti, where you get a close look at wine production and aging. Guides there take time to explain secrets of olive oil making too, which adds another layer of appreciation for Tuscany’s culinary riches. According to reviews, you can try most of the available wines at the first winery, along with their olive oil, honey, saffron, and even basaltic vinegar produced right on the farm—imagine the taste of saffron from local saffron fields!

One reviewer appreciated the behind-the-scenes glimpse into distilling processes and the chance to purchase aged balsamic vinegar at a bargain. Such insights aren’t just for wine lovers; they give you a fuller understanding of the region’s food culture. The tasting sessions are praised for being generous and informative, often led by passionate hosts.

San Gimignano: A Medieval Jewel

After the first winery, the tour heads to San Gimignano, where the main attraction is its medieval skyline with fifteen towers that have earned it the nickname “Medieval Manhattan.” You will have free time to wander the narrow streets, shop for local crafts, or just soak in the scenery. One of the standout moments, according to reviews, is sampling the world champion gelato at Gelateria Dondoli, voted the best gelato shop worldwide in 2024.

The town’s atmosphere is lively yet laid-back, and many travelers find it a genuine highlight—especially those who like cute towns with a bit of history and flavor. Just be aware that the time in San Gimignano can be brief, so if you want a thorough exploration, it’s best to go with the understanding that this visit is more about a taste than a deep dive.

Visiting the Second Winery & Tuscan Lunch

The second stop is another family-owned vineyard, where you’ll enjoy a Tuscan light lunch paired with wine tastings. This is a more relaxed setting, often praised for the delicious meat and cheese pairings and the stunning vineyard views. Be mindful, though, that some reviews found the wines at this second stop less exciting, with less detailed explanation. Still, the meal and the setting make it worth the visit.

During the tasting, you’ll encounter a 30-year-old balsamic vinegar and truffle-infused olive oil, which many find fascinating and a true taste of Tuscany’s culinary heritage. You might find yourself wanting to buy these products to take a piece of Tuscany home.

Panoramic Views & Final Stop at Piazzale Michelangelo

On the way back to Florence, the tour makes a stop at Piazzale Michelangelo, a spot renowned for its panoramic view of Florence’s rooftops and the Duomo. Many reviews mention this as a romantic or inspiring way to end the day, appreciating the stunning vistas and the chance to reflect on your Tuscan adventure.

Who Will Love This Tour

This experience is best suited for wine enthusiasts, curious food lovers, and travelers who enjoy small-group, authentic experiences. The guides are praised for their friendliness and knowledge, making it especially good for those who want to learn about Chianti wines and Tuscan food. It’s also ideal for those who appreciate scenic towns and history, with San Gimignano providing a perfect snapshot of medieval Italy.

If you’re after a luxurious, high-end tour with gourmet meals, you might be disappointed. But if you want a well-rounded, friendly, and genuine day out that combines wine, scenery, and local flavor, this tour hits the mark.

Price & Practicalities

At about $215 per person, the tour offers a lot of value considering the inclusions—two winery visits, tastings, a meal, and sightseeing. The small group size makes it feel exclusive and avoids the crowds common in larger tours. It lasts about eight hours, starting outside a cafe near Florence’s train station, making logistics straightforward.

Be sure to wear comfortable shoes and casual clothes, as you’ll be walking and exploring outdoor areas. The tour is available in English and Italian, and booking can be flexible with free cancellation up to 24 hours before.

Final Thoughts

This day trip from Florence is a well-reviewed, engaging way to explore Tuscany’s wine culture and medieval towns. The combination of organic wineries, small group charm, and the chance to savor world-class gelato makes it stand out. The guides’ knowledge and friendly approach elevate the experience, making it more than just a sightseeing tour.

While the lunch may not be gourmet, the overall value, scenic stops, and authentic immersion make it a worthwhile day. It’s especially suited for those who want to learn about Chianti wines, enjoy Tuscany’s landscape, and have a relaxed yet informative experience with new friends.

If you love wine, scenic towns, and local food, this tour delivers a satisfying slice of Tuscany in just one day.

FAQs

How many wineries will I visit on this tour?
You’ll visit two family-run wineries, each offering their own wines and stories.

Is the tour suitable for people with mobility issues?
Yes, it’s wheelchair accessible, but you should wear comfortable shoes and be prepared for some walking.

How long is the tour?
The entire experience lasts about 8 hours, starting and ending in Florence.

What is included in the price?
The price covers visits to both wineries, tastings, a typical Tuscan light lunch, San Gimignano exploration, and a stop at Piazzale Michelangelo.

Can I buy wine and products at the wineries?
Yes, you’ll have the chance to purchase wines, aged balsamic vinegar, olive oils, honey, and saffron at reasonable prices.

Are the guides knowledgeable?
Yes, reviews highlight guides like Christian and Daniel for their friendliness and depth of knowledge about wine, Tuscany, and local culture.

What should I bring?
Comfortable shoes and casual clothes are recommended; sunscreen and water are also useful in summer months.