Chianti isn’t just famous for its bold, Sangiovese-based wines—it’s also a region that offers a rich variety of wine experiences that appeal to every palate and interest. Whether you’re after a relaxed tasting at an organic winery, a private shore excursion with scenic views, or a hands-on cooking and wine pairing, Chianti delivers. One standout is the Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area. It combines intimate vineyard visits with the chance to sample 3-6 wines in a genuine farm setting, earning a perfect 5-star rating. It’s a prime example of how tasting local wines in their authentic environment enhances the experience.
For those in port, the Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour offers a full-day private tour. It’s perfect if you want a personalized exploration of Tuscany’s rolling hills, combined with visits to Greve in Chianti and a scenic drive through classic Tuscan landscapes. This variety across tours ensures you’ll find something that fits your schedule and style.
1. Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
This highly-rated tour offers a 1.5-hour visit to a small organic winery situated between Radda and Panzano, right in the core of the Chianti Classico. You’ll explore the vineyards and learn about organic wine production from passionate staff. The tour culminates in a tasting where you can sample 3 to 6 wines alongside local snacks like bread and olive oil produced on-site. With a perfect 5.0 rating from over 120 reviews, visitors love Francesco’s engaging explanations and the remote, rustic setting that makes you feel like a true insider. Bottom line: this tour is ideal if you want an authentic, relaxed experience without breaking the bank, especially if you’re keen to understand organic wine-making.
2. Livorno Shore Excursion: Chianti and Tuscany Countryside Private Wine Tour
Spending a day in port? This 9-hour private tour is perfect for a personalized exploration of Chianti’s stunning landscape. Starting with a scenic 90-minute drive from Livorno, you’ll visit Greve in Chianti, famous for its lively Piazza Matteotti and historic shops like Falorni butcher. The tour then continues through vineyard-lined roads to a local winery, where your private guide explains the winemaking process, and you sample some of Tuscany’s top wines and olive oils. The overall experience earns top marks thanks to the knowledgeable guide Mario and the flexibility of a private tour. Bottom line: this is ideal if you seek a comprehensive, luxury day out that combines scenic drives, cultural highlights, and wine tasting.
3. Greve in Chianti Wine Tasting and Winery Tour
For a deeper look behind the scenes, the Greve in Chianti Wine Tasting and Winery Tour dedicates roughly 1.5 hours to exploring a family-run, organic winery. You’ll tour the vineyards, learn about Chianti Classico’s history, and taste four different organic wines inside the cellar—paired with regional cheeses and salami. The guide, Maurizio, is praised for his warm hospitality and extensive knowledge, making this tour both educational and personal. Visitors love the authentic atmosphere and the chance to sample wines directly from the source. Bottom line: perfect for those who want an intimate experience and to taste regional products in a friendly setting.
4. Montefioralle Winery – Tour and Wine Tasting in Chianti
This 1-hour 15-minute tour offers a chance to visit a small, family-run winery in Montefioralle, one of Chianti’s most picturesque villages. You’ll explore the vineyard and learn about traditional winemaking methods, then sample four house wines, including Chianti and Vin Santo. The outdoor tasting spot provides scenic views of vines and the historic village, creating a charming setting. Many reviews highlight the warm, welcoming owner and the high-quality wines, with some guests even ordering bottles for delivery. Bottom line: this tour balances intimacy and quality, suited for quiet wine lovers wanting a personal touch.
5. Winery Tour & Gourmet Tasting in Montalcino
Moving slightly south, this 2.5-hour experience combines a guided vineyard walk with a gourmet tasting. You’ll learn about biodynamic viticulture and enjoy 6 wines in three flights, paired with specially crafted Gourmet Bites. The setting offers fantastic views of Montalcino and a chance to understand the nuances of high-quality Brunello wines. The guide’s enthusiasm and the pairing of food with wine make this a memorable, immersive experience. Bottom line: great for wine enthusiasts who want a sophisticated tasting with an upscale flair.
6. Private Tuscan Cooking Class And Wine Tasting in Radda in Chianti
Here, you combine culinary skills with wine in a private setting. Led by local cooks in a scenic Tuscan home, you’ll learn to prepare up to three Italian dishes, including homemade pasta. The class includes a wine and olive oil tasting and a home-cooked meal with vegetarian and vegan options. Guests love the personalized attention and the chance to recreate authentic dishes afterward. At just $166, the value is excellent considering the intimate setting and the skills learned. Bottom line: ideal for foodies who want to deepen their understanding of regional cuisine with wine pairings.
7. Gourmet Wine & Food Tasting
For an elegant, shorter experience, this Gourmet Wine & Food Tasting offers six organic wines paired with six Gourmet Bites, all served during a 1.5-hour guided session. Held in Montalcino, it’s perfect for a quick, high-quality introduction to Tuscany’s wine and culinary delights. The friendly atmosphere and personalized pairings are highly praised. Bottom line: a refined, memorable tasting for those with limited time but high expectations.
8. Winery tour & wine tasting in Montalcino
This 1 hour 45-minute tour combines a walk through the vineyard with a seated tasting of six wines. Visitors rave about the breathtaking location and the in-depth explanation of biodynamic viticulture. The tour offers a chance to taste the wines independently after some guidance, making it flexible. Reviewers mention this being the best vineyard experience they’ve had, with some noting the lack of commercialization. Bottom line: excellent for those who want a comprehensive yet authentic experience with stunning scenery.
9. 3-Hour Private Food and Wine Experience in Montalcino
This private experience combines a visit to the Molino di Sant’Antimo cellar with a 4-course lunch, paired with wines like Gina Rosato and Il Bianco Chardonnay. It’s a great choice for visitors wanting an intimate, full tasting and regional meal. The host Lucilla is praised for her hospitality. At three hours, it’s a good balance of immersion and relaxation. Bottom line: suited for those who want a combination of wine, regional cuisine, and a cozy atmosphere.
10. Private Hike and Wine Experiences in Chianti
If your ideal day involves walking and exploring alongside wine tasting, this full-day tour is perfect. You’ll trek through vineyards, discover hidden corners, and enjoy tastings in scenic spots. It’s best for active travelers who want to combine outdoor adventure with wine. The reviews emphasize the discovery of artistic, gastronomic, and artisanal treasures during the walk. Bottom line: excellent for those seeking an active, immersive experience in Chianti’s landscape.
11. Radda in Chianti: Wine Tasting Tour with lunch at the Winery
This tour provides a guided cellar tour of Monterinaldi Castle and a traditional Tuscan lunch in an 18th-century villa. The 2-hour experience includes wine tasting of three wines, including a Vinsanto, with scenic countryside views. Visitors highlight the informative guide and delicious food, making it a great choice for those wanting a combination of history, scenery, and regional cuisine. Bottom line: suited for travelers who want an educational, relaxing day with good food and wine.
12. Classic Wine Tasting in Montalcino
A quick 45-minute experience, this wine tasting is an ideal introduction. You’ll sample six wines across three flights while enjoying a cinematic journey through Tuscany’s countryside. It’s simple but highly rated for quality and atmosphere. Perfect if you’re short on time but want a taste of Tuscany’s finest wines. Bottom line: best for those after a brief but quality-focused experience.
13. Gourmet Wine Tour
At 5 hours long, this full-day tour is designed for wines and food lovers. You’ll explore Chianti’s vineyards and enjoy the region’s signature Brunello di Montalcino paired with traditional Tuscan dishes. The focus on both wine and culinary traditions makes it ideal for those wanting a deep dive into local flavors. The reviews are glowing, emphasizing the breathtaking scenery and excellent wine and food pairing. Bottom line: best for travelers wanting an all-encompassing, indulgent experience.
$301.24 per person
14. Montalcino: Exclusive Picnic in the Vineyard with Wine Basket
This simple yet charming option offers a picnic in the vineyards with a basket of regional products like bruschetta, cured meats, and cheeses. The experience lets you enjoy nature and wine in a relaxed setting. It’s perfect for couples or quiet days outdoors, especially if you prefer a self-guided picnic with a scenic backdrop. Bottom line: a laid-back, intimate experience for wine lovers who enjoy picnics.
$35.28 per person
15. Wine Tasting, Dinner and Cooking Class Under the Sunset
This 5-hour evening experience combines a cooking class, a 4-course dinner, and wine tastings of Brunello di Montalcino. Led by a chef, it’s perfect for culinary enthusiasts who want to learn regional recipes like homemade pasta (“pinci”) while sipping on regional wines. Hotel transfers make it convenient for evening relaxation. Reviewers mention the unforgettable experience and the chance to learn skills they can take home. Bottom line: suited for foodies seeking a memorable culinary and wine adventure at sunset.
$209
How to Choose the Best Chianti Wine Tour for You
When selecting a wine tour in Chianti, consider your budget, schedule, and interests. For a quick, authentic taste of organic wines, the Tour and Tasting at an Organic Winery is an excellent choice. If you’re arriving via cruise, the Private Shore Excursion offers a full-day, personalized experience with scenic drives. For those wanting a culinary twist, the Private Cooking Class combines hands-on cooking with regional wines, ideal for food lovers.
Budget-conscious travelers can opt for shorter tastings like the Classic Wine Tasting, while serious enthusiasts may prefer full-day tours like the Gourmet Wine Tour. Early booking is recommended, especially for private and small-group experiences, to secure your preferred date and setting.
Final Thoughts
Chianti offers a range of wine experiences that cater to every taste, from casual tastings to immersive culinary days. If you’re looking for authentic, off-the-beaten-path visits, the organic winery tour delivers a genuine experience. For a luxury, personalized day, the private shore excursion ensures you see the best while enjoying the scenery. Meanwhile, those wanting to learn and cook will find the private Tuscan cooking class and sunset dinner to be unforgettable.
No matter your budget or interests, Chianti’s vineyards and wineries promise memorable moments. To avoid missing out, consider booking early—these tours fill up quickly, especially during the peak season in late spring and fall. Now, all that’s left is to choose your adventure and start planning your Tuscan wine escape.