Tuscany is famous for its rolling hills, historic towns, and, of course, its exceptional wines. While you could spend days exploring the region’s vineyards, what really makes a wine tour special is its authenticity—touching the land, tasting the wines where they’re made, and learning about centuries-old traditions. We’ve picked out some of the best options to help you decide which Tuscan wine adventure suits your style. Whether you prefer a day trip to San Gimignano and Volterra or a private winemaker experience, this list has you covered.
Of the options, we especially like the Wine Tasting & Tuscany Countryside tour because it combines visits to must-see towns with wine tasting in an intimate setting, and the 3-day private winemaker experience for those wanting an immersive stay. For a quick, budget-friendly taste of Tuscany’s wine culture, the Visit to the Cellar with Wine & Food Tasting over the Val d’Orcia offers a flavorful introduction. If you prefer something unique, the Carriage ride among the vineyards provides a charming, organic experience. Keep reading for detailed reviews and picks.
1. Wine Tasting & Tuscany Countryside, San Gimignano & Volterra
At number one on our list, this full-day small-group tour captures the best of Tuscany’s countryside, combining history, scenic towns, and wine tasting. You’ll meet your guide in a central location and hop into an air-conditioned vehicle for the roughly 9-hour adventure.
The journey starts with a visit to Volterra, an ancient Etruscan city filled with Roman ruins and a fortress that offers stunning views. From there, you’ll head to a local winery for a tasting featuring multiple wines and snacks—an ideal way to learn about Tuscan varietals in a relaxed setting. The final stop is San Gimignano, a UNESCO World Heritage site famous for its medieval towers and vibrant atmosphere.
Rated 5.0/5 based on 77 reviews, travelers love how this tour offers a more authentic experience outside the tourist traps. Many mention the passionate hosts and the chance to sample high-quality wines while enjoying the countryside. One reviewer said, “The wine tasting experience was unexpectedly special,” highlighting the personal touch of this tour.
Bottom Line: If you want a comprehensive day that combines history, iconic towns, and excellent wine, this tour is hard to beat. It’s especially suited for those who want a relaxed, small-group experience with knowledgeable guides.
2. Visit to the Cellar with Wine & Food Tasting over the Val d’Orcia
At around $44.71, this short, two-hour group tour is a budget-friendly way to taste some of Italy’s finest wines and enjoy authentic Tuscan cuisine. Here, all the details are taken care of, making it ideal for travelers seeking a straightforward, educational experience.
The tour includes a visit to a Montecucco DOCG winery, where your connoisseur guide explains the region’s grape-growing process. You’ll enjoy a laid-back lunch overlooking the Val d’Orcia, featuring artisanal cured meats, cheeses, and Seggiano’s best wines. The scenic views of rolling hills provide the perfect backdrop for this tasting.
Reviewers praise this experience for its informative guide and delicious food pairings. One noted, “Learning about the wine process while enjoying the view made for a perfect afternoon.” It’s perfect if you’re short on time but still want a taste of Tuscany’s wine and culinary traditions.
Bottom Line: A fantastic introduction to Tuscan wines combined with local flavors, this tour is ideal for travelers on a budget or those with limited time who want a genuine, small-group experience.
3. Livorno Shore Excursion: Pisa, Florence and Chianti Wine Private Day Trip
For around $480 per person, this private 9-hour tour is perfect for cruise travelers who want a tailored experience. It’s the only tour on our list that combines iconic cities with a wine tasting in a single day.
Your guide will take you from Livorno to Pisa to snap photos of the Leaning Tower and explore Piazza dei Miracoli. Then, a scenic drive brings you to Florence, where you can admire the Duomo and Michelangelo’s view from Piazzale Michelangelo. The highlight is a visit to a local winery, where you’ll sample renowned Tuscan wines like Chianti, paired with regional snacks.
Reviews highlight how this tour offers customizable schedules and a personalized experience. One traveler shared, “Our guide Massimo was waiting when we arrived, making the day seamless,” reflecting the convenience of a private trip.
Bottom Line: This tour suits those arriving by cruise or visitors who want a comprehensive, private day with city highlights and wine in one package — ideal for those who appreciate flexibility and personalized attention.
4. In a carriage among the vineyards, visit of the cellar, tasting of organic wines
Price at $89.01, this unique experience lets you see Tuscany’s Upper Maremma in style—via an elegant carriage ride pulled by horses. It’s perfect for travelers seeking something a little different from typical winery visits.
The tour starts with a warm carriage ride through Casadei estate’s biodiverse landscape, followed by a visit to the cellar where organic wines are produced using biodynamic practices. You’ll taste three wines accompanied by local artisan products, all while soaking in the peaceful scenery. The experience lasts about two hours and has received rave reviews for its authenticity and charm.
One review states, “Beautiful experience, back to nature at the Casadei estate, with wines and staff that made us feel very welcomed.” It’s especially good for those who want a relaxed, scenic outing with an emphasis on organic and sustainable practices.
Bottom Line: If you enjoy combining quiet countryside views with organic wines, this elegant carriage tour offers an intimate, memorable experience that’s perfect for couples and small groups.
5. Sorano and its wonders, The Vie Cave and wine cellars
Priced at about $97.44, this 2-3 hour tour is a fascinating blend of Etruscan history, myth, and wine. Starting from the Hotel della Fortezza, it walks you through Sorano’s ancient streets and underground caves, following the paths carved by the Etruscans.
You’ll explore the Vie Cave, underground roads that once linked Tuscana’s necropolises, and enjoy panoramic views from the hilltop. The highlight is a visit to a local cellar where young winemakers will introduce their methods and showcase regional wines. The tour combines history with a relaxed tasting, perfect for history buffs or those interested in authentic, small-scale producers.
One reviewer called it a “once-in-a-lifetime hike and wine tasting,” emphasizing its unique mix of adventure and flavor.
Bottom Line: Ideal for those who want an active outing with cultural insights, this tour balances history and wine in a way that’ll leave you both educated and satiated.
6. La Maliosa Farm Experience & Wine Tasting
At just $45.10, this 1.5-hour experience offers a quick, intimate look into natural and organic wines from La Maliosa. You’ll start with a walk through the vineyard, learning about the Méthodo Cosino and the region’s historic grape varieties.
The tasting includes two natural wines paired with local cheeses and cured meats, plus homemade bread and Tuscan extra-virgin olive oil. The guide is a local expert who shares insights into organic farming and winemaking. The setting is relaxed, and reviews praise the friendly atmosphere and high-quality wines.
This tour is perfect if you want a small, private experience that emphasizes sustainability and authentic flavors.
Bottom Line: For travelers looking for a short, rich tasting with a focus on organic wines, La Maliosa offers excellent value and a memorable experience for small groups.
7. Tuscany: Ripalte Design Winery Wine and Cheese Tasting Tour
Costing around $67.97, this 2-hour tour explores one of the 14 Design Wineries of the Toscana Wine Architecture Circuit on Elba Island. It combines wine and cheese tasting with spectacular sea views.
You’ll learn about the winemaking process and the drying of grapes, then enjoy a tasting of three different wines paired with cured meats and cheeses. The panoramic terrace offers stunning views of the sea, making it a unique setting for a tasting tour. The guide shares insights into the regional wine culture, making it engaging and informative.
Reviewers appreciate the friendly guide and the beautiful location. One noted, “Julia made the tour very enjoyable with her explanations,” reflecting the personal touch.
Bottom Line: This tour is ideal for travelers wanting a scenic, relaxed tasting experience with a focus on Tuscan wines and local flavors on Elba Island.
8. 3-day private experience as a winemaker at a wine resort in Tuscany
Priced at $1,155.66 per group, this immersive 3-day experience is perfect for those serious about wine. Staying in an authentic Tuscan village, you’ll learn winemaking techniques from experts, visit the vineyards, and participate in red wine tastings.
You’ll have access to the cellar and learn about Sangiovese grapes, with plenty of hands-on activities. The stay includes accommodation, breakfast, and dinners, making it a complete experience. It’s best suited for travelers who want to dive deeply into Tuscan winemaking rather than just tasting.
Reviews mention the personalized guidance and the chance to learn real winemaking. It’s a rare chance to spend multiple days in Tuscany, gaining skills and memories that last.
Bottom Line: Best for wine lovers ready to invest time and money into a comprehensive, hands-on experience; ideal for those who want to go beyond tasting.
9. Pisa and Wine Tasting in Tuscany from Livorno
This 6-7 hour private trip at about $1,023.94 for up to eight people combines Pisa’s iconic landmarks with a scenic Tuscany winery visit. It’s perfect for travelers who want a blend of city sightseeing and wine tasting.
The day begins with the Leaning Tower, then moves to a Tuscan vineyard for a light lunch and wine tasting. The experience balances cultural sightseeing with relaxing wine immersion, making it suitable for those who want a taste of both city and countryside.
Reviews mention how well-organized and informative the trip is, with one traveler saying, “Our guide made the day seamless and memorable.”
Bottom Line: Suitable for those seeking a flexible, yet curated day exploring Pisa and experiencing Tuscan wines, especially if you prefer private tours.
10. Wine tasting and guided tour of the cellar
Costing just $23.17 per person for about an hour, this historic farm experience in Montecatini offers a basic but authentic introduction to wines and oils.
The tour includes tasting three wines with local bruschetta, cheeses, and cold cuts. The guide explains the winemaking process and the farm’s history, making it a straightforward, no-frills option for those seeking a quick, authentic experience.
Reviews are limited but positive, emphasizing the personal attention and quality of the wines.
Bottom Line: Great for travelers on a budget or those who want a quick, authentic insight into Tuscany’s wine and oil traditions without a lengthy commitment.
How to Choose Your Perfect Tuscan Wine Tour
When selecting a wine tour, think about your budget, time, and what experience appeals most. If you want a full-day adventure with sightseeing and tastings, the Wine Tasting & Tuscany Countryside is unbeatable. For those focused on learning the craft, the 3-day private winemaker experience offers hands-on involvement. Budget travelers might prefer the Val d’Orcia wine & food tour or the small guided cellar tastings. If you’re after something unusual, consider the carriage ride among the vineyards for a charming, organic experience.
Also, consider logistics—are you arriving by cruise, or staying in Florence? For cruise visitors, the private Pisa and Florence day trip offers flexibility. Book early—especially in peak season—since Tuscany’s wine tours fill up quickly, and many experiences are private or small-group.
Final Thoughts
Tuscany offers a diverse array of wine adventures that range from simple tastings to full immersion in winemaking. Couples looking for romantic moments will love the carriage ride or small-group tastings, while serious wine enthusiasts can’t go wrong with the 3-day private experience. For a quick taste, the Val d’Orcia tour provides excellent value, while the private city excursions serve those with limited time but high expectations.
No matter what you choose, booking in advance ensures you won’t miss out on these memorable experiences. Tuscany’s wines are as rich as its landscapes—so take your pick and enjoy a truly flavorful journey.