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Discover Tuscany’s finest with a semi-private Chianti wine tour, featuring three wineries, expert tastings, and a delicious Tuscan lunch, all in a small group setting.
A Taste of Tuscany: The Chianti Wine Tour with Tastings (Semi-Private Experience)
If you’re dreaming of sipping some of Italy’s most iconic wines while soaking up the stunning Tuscan scenery, this Chianti Wine Tour with Tastings ticks all the boxes. Offering a carefully curated journey through three different wineries, expert insights on Super Tuscans, and a hearty Tuscan lunch, this tour promises an engaging and delicious day out from Florence. The small group size—limited to just eight—sets the scene for personalized attention and a more relaxed atmosphere.
What we really love about this experience is the combination of intimate, expert-led tastings and the chance to explore charming Tuscan villages along the way. Plus, traveling in a luxury Mercedes van with onboard Wi-Fi makes the day comfortable and convenient. One consideration? Since bookings are made on average 61 days in advance, it’s wise to plan ahead if you want a spot, especially during high season. This tour will appeal to wine lovers, foodies, or anyone craving a small-group, authentic taste of Tuscany without the crowds.


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This 7-hour tour kicks off in Florence at 9:30 AM, giving you plenty of time to soak in the day’s experiences. You’ll be picked up in a luxury Mercedes minivan, a move that immediately elevates the experience from the start. With a maximum of eight travelers, the ambiance is cozy, and your guide—an English-speaking wine expert—can tailor the commentary to your interests.
Stop 1: Castello di Gabbiano
Your first stop is at the picturesque Castello di Gabbiano, a historic estate with sprawling vineyards. Here, you’ll have around 50 minutes to explore and taste wines directly from the source. Reviewers mention that this visit offers a beautiful setting and “good wines,” setting a promising tone for the day. The estate’s history and the chance to see the vineyards up close give an added layer of authenticity.
Stop 2: Greve in Chianti
Next, you head to Greve in Chianti, a charming town known for its quaint piazzas and traditional vibe. Visiting a winery here, you’ll again enjoy a 50-minute tasting. Travelers praise the delicious lunch and the opportunity to wander through a local town—it’s the perfect blend of tasting and sightseeing.
Stop 3: Diadema Wine & EVO
The third stop is at Diadema, a boutique winery specializing in EVO (extra virgin olive oil) and fine wines. The tasting here lasts about 50 minutes and is described as intimate, with visitors appreciating how the host shares insights into wine-making techniques. Multiple reviews emphasize how this stop provides access to wines that some guests even shipped home afterward, highlighting their quality.
Stop 4: Ristorante Diadema
Your day culminates with a gourmet Tuscan lunch at Ristorante Diadema, lasting about an hour. Guests describe the meal as delicious and the atmosphere as charming. Pairing regional dishes with more wine, this sit-down meal is a great way to relax and reflect on the day’s tastings.
Throughout the day, you’ll sample a variety of Tuscan wines, including whites, rosés, Chiantis, and Super Tuscans—the region’s prized red blends. The tours include olive oil and typical local products for tasting, adding to the food & wine experience. One review noted how “the wines are delicious” and that two wineries were so good they shipped bottles home, proving the quality is genuine.
Traveling in a small group enhances the experience significantly. Several reviewers mention how the intimate setting allowed for more interaction, personalized explanations, and a less rushed visit. As one guest put it, “Our tour guide, Lorenzo, was informative and fun,” which really highlights how the guide’s personality can turn a good tour into a memorable one.
The guide, a very knowledgeable sommelier named Matteo in one review, is praised for being patient, friendly, and informative. He shares insights into why certain wines are considered Super Tuscans and provides tips on developing your palate. Traveling in a luxury Mercedes minivan helps keep the group comfortable, and the included Wi-Fi is a thoughtful perk, especially if you want to share updates or photos during the day.
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At $227.93 per person, the price might seem steep at first glance, but considering it covers transportation, expert guidance, three wine tastings, olive oil, a gourmet lunch, and the chance to visit three wineries, the value is clear. Guests consistently mention that the quality of wines, the lunch, and the personalized experience more than justify the cost.
This experience is ideal for wine enthusiasts eager to deepen their understanding of Tuscan varietals, especially Super Tuscans. Food lovers will appreciate the gourmet lunch and regional tastings, while those seeking a more intimate, less commercial tour will find the small-group setting refreshing. It’s also perfect for travelers who value comfortable transportation and expert guidance without the crowds.
However, consider that it’s not a large-group party—so if you prefer a more lively, social scene with many participants, this might not be your best fit. Also, children under 18 are welcome but will only be served non-alcoholic beverages, and the tour requires a certain level of mobility to enjoy the sights and tastings fully.

The Chianti Wine Tour with Tastings offers a well-rounded, authentic glimpse into Tuscany’s famed wine country. Small-group size, expert guides, and a carefully curated itinerary make it a standout choice for those who want more than just a bus ride and a few tastings. You’ll experience the scenic beauty of the Chianti countryside, learn about regional wines—including the coveted Super Tuscans—and enjoy a delicious Tuscan meal that complements the day’s wines perfectly.
This tour strikes a nice balance between education and enjoyment, making it especially suitable for wine lovers, foodies, or anyone looking for a relaxed, intimate experience just outside Florence.

Is transportation included?
Yes, the tour includes pickup and drop-off in Florence via a luxury Mercedes minivan with Wi-Fi onboard.
How many wineries will I visit?
You’ll visit three wineries, each offering tastings and insights into their wine-making process.
What does the lunch include?
The lunch is a traditional Tuscan meal served at Ristorante Diadema, paired with more wine. Reviewers describe it as delicious and well-organized.
Are children allowed on this tour?
Children under 18 are permitted but will only be served non-alcoholic beverages, and minors must be accompanied by at least one adult.
How long is the tour?
The entire experience lasts about 7 hours, starting at 9:30 AM and returning to Florence.
What wines will I taste?
Expect a selection of regional whites, rosés, Chiantis, and Super Tuscans, with some wineries offering the chance to sample high-quality wines.
Is this a good tour for wine novices?
Absolutely. The knowledgeable guide shares tips on developing your palate and explains wine styles clearly, making it suitable for all levels.
How far in advance should I book?
On average, travelers book about 61 days ahead, especially during peak seasons, to secure a spot given the small group size.
In summary, this semi-private Chianti wine tour offers a genuine, relaxed, and educational adventure into Tuscany’s renowned wine scene. Perfect for those who want to enjoy the scenery, taste exceptional wines, and have a memorable day in good company.