Small Intimate Group: San Gimignano – Two Wine Tours with lunch

Exploring Tuscany’s Charm: A Detailed Look at the Small-Group San Gimignano and Wine Tasting Tour

If you’re dreaming of a day filled with rolling vineyards, medieval streets, and authentic Italian flavors, this small-group tour from Florence promises just that. It combines a scenic walk through the UNESCO-listed town of San Gimignano with visits to two family-run wineries in the Chianti region — all wrapped up in about eight hours of leisurely, personalized discovery.

What we love most about this experience is the personalized attention that comes with the small group size, capped at just eight travelers. It allows for more flexible pacing and genuine interactions. Plus, the inclusion of lunch, wine tastings, and olive oils makes it a fantastic value, especially considering the convenient hotel pickup and drop-off. One thing to keep in mind is that some attractions, like museums or towers, are not included in the ticket price, so if you’re eager to climb the towers of San Gimignano, you might want to explore those separately.

This tour is ideal for those who want to enjoy Tuscany’s highlights without feeling rushed or lost in a large crowd. It’s perfect for couples, small groups of friends, or solo travelers who appreciate intimate experiences and quality wines. If you’re seeking authentic flavors, stunning views, and expert guides, this trip is likely to tick all the right boxes.

Key Points

• Small Group Experience: With only up to 8 travelers, expect personalized attention and a relaxed pace.
• Authentic San Gimignano: Free time to explore this historic hilltop town’s medieval streets and spectacular views.
• Two Family Wineries: Enjoy visits to two different wineries in Chianti, with tastings of wines, olive oils, and food pairings.
• Hassle-Free Transportation: Includes round-trip pickup and drop-off from Florence, making logistics simple.
• All-Inclusive Value: Lunch, wine tastings, taxes, and fees are covered in the price, providing a seamless experience.
• Flexible and Balanced Itinerary: Each stop lasts about two hours, enough for exploration without feeling rushed.

A Deep Dive into the Experience

The Journey Begins: Pickup and San Gimignano

Your day kicks off at 9:00 am with hotel pickup in Florence, a real godsend if you’re staying centrally. The comfortable transport whisks you out of the city and into the scenic Tuscan countryside, giving you glimpses of vineyards and cypress-lined roads en route. It’s a stress-free start, especially for those who dislike figuring out public transport or navigating narrow Italian streets with a rental car.

Once in San Gimignano, you get a guided introduction to this UNESCO World Heritage site, known for its medieval towers and well-preserved architecture. The tour’s pace allows you to absorb the history and take plenty of photos, especially of the iconic skyline dotted with historic towers. The free time here (about two hours) is ample for wandering the cobblestone streets, browsing local shops, or simply savoring a gelato while soaking in the views.

San Gimignano: A Medieval Marvel

The town’s charm lies in its well-preserved medieval character, with narrow alleys and stone buildings that seem untouched by time. Reviewers like Linda B mentioned that “this tour was the highlight of our family vacation,” emphasizing how the town’s atmosphere is both picturesque and immersive. The guide provides insights into its history, but you’re free to explore at your own pace afterward. If you’re a fan of architecture or history, you’ll appreciate how San Gimignano’s towers once symbolized wealth and power — a perfect photo backdrop.

Castellina In Chianti: Family Winery Visit

After soaking up San Gimignano’s charm, the tour continues to Castellina In Chianti, a small, family-run winery. Here, you’ll enjoy a food and wine pairing session that goes beyond simple tastings. The host is often a family member, sharing stories about their heritage and winemaking process, which adds a layer of authenticity to the experience.

Reviewers like Rodrick P appreciated the intimate atmosphere, describing Anna Marie (the guide) as “the best,” and noting that “this was one of the highlights of our trip.” The tasting includes Tuscan wines paired with local foods, which are described as delicious and well thought out. Many mention the quality of the wines and the olive oils, often noting how the flavors are notably fresh and authentic. This stop offers more than just tasting — it’s about understanding the passion behind each bottle.

Radda in Chianti: The Second Winery

The second winery visit in Radda continues the wine journey. This town’s setting offers sweeping views of vineyards and rolling hills, making it a perfect backdrop for more tastings. Expect to sample a variety of wines, which are carefully selected to showcase the region’s diversity.

Guests frequently mention the “excellent wine selection” and the “delicious tapas,” which enhance the tasting experience. The guide’s explanations help you appreciate the nuances between different wines, and some reviewers noted that they discovered new favorites they hadn’t tried before. The approximately two hours here allow for a relaxed tasting session, providing plenty of time to ask questions and soak in the countryside ambiance.

Lunch: Savoring Tuscan Flavors

Included in the tour is a hearty lunch, often featuring local specialties and farm-fresh ingredients. Guests have praised the meal for its quality and authenticity. It’s the perfect way to refuel after a morning of exploration and wine tasting. Vegetarian options are available if you request in advance, ensuring all dietary needs are met.

The Return Journey

After the last tasting, the transport takes you back to Florence, typically arriving around 5 pm. The tour’s structure ensures you’re never rushing, allowing genuine relaxation and enjoyment of the day.

Analyzing the Value

At a price of roughly $276.57 per person, this tour offers significant value, considering everything included. The small group size enhances the experience, providing a more personalized touch that larger tours can’t match. The hotel pickup and drop-off eliminate transportation worries, and the all-inclusive tastings and lunch mean you won’t be constantly reaching for your wallet.

While the tour doesn’t include entrance tickets to towers or museums, the focus on tasting and sightseeing is more than enough for most travelers seeking an authentic, flavorful day. The reviews highlight the quality of the wine and food, often calling out the delicious tapas and the excellent selection of wines that cover a broad spectrum of local flavors.

Who will love this tour?

It’s perfect for wine enthusiasts, food lovers, or travelers who want a deeper, more intimate experience in Tuscany without the crowds. Small groups mean you can ask questions and engage with your guide, Anna Marie, who is praised for her warmth and knowledge. If you enjoy picturesque towns, scenic drives, and authentic wine and food experiences, this is a great pick.

The Sum Up

This small-group wine tour from Florence strikes a wonderful balance between structured sightseeing and flexible exploration. It’s especially well-suited for those seeking intimacy, quality wines, and authentic Tuscan flavors in a relaxed setting. The visits to San Gimignano and two local wineries provide a taste of Tuscany’s rich terroir, complemented by delicious food and a comfortable, hassle-free transport experience.

For travelers who value personalized attention, authentic tastings, and scenic views, this tour delivers on all counts. Plus, the positive reviews and high ratings reflect its quality and the genuine care of the guides—making it a memorable highlight of any Tuscan adventure.

FAQ

Is hotel pickup included in the tour?
Yes, the tour offers hotel pickup and drop-off from Florence, making logistics simple and stress-free.

How long is the entire tour?
The experience lasts approximately 8 hours, from 9:00 am pickup to return in the late afternoon.

What’s included in the price?
All taxes, fees, handling charges, lunch, wine tastings, and the guide are included. Entrance tickets to towers or museums are not.

Is there a minimum group size?
Yes, a minimum of 4 people is required for the tour to operate, with a maximum of 8 travelers.

Can I participate if I don’t drink alcohol?
Yes, most travelers can participate, but note that the minimum drinking age is 18. Non-alcoholic options are likely available upon request.

How much free time do I have in San Gimignano?
You’ll have about two hours for self-guided exploration, shopping, or just soaking in the views.

Are dietary restrictions accommodated?
Vegetarian options are available, but it’s best to advise at the time of booking.

What should I wear?
Smart casual attire is recommended, along with comfortable walking shoes for cobblestone streets.

What happens if the weather is poor?
The tour requires good weather; if canceled due to rain, you’ll be offered an alternative date or full refund.

This tour is a fantastic way to experience Tuscany’s flavors, history, and scenery in a relaxed and intimate setting. Whether you’re a wine lover or simply seeking a memorable day outside Florence, it’s an experience worth considering.