Pisa isn’t just about its famous leaning tower and stunning cathedral; it’s also a great base for exploring Tuscany’s legendary wine country. While many travelers focus on the monuments, savvy visitors know that the Tuscan countryside’s vineyards hold some of Italy’s finest wines, often just a short drive from Pisa’s historic center. We love how some tours offer intimate, small-group experiences that really dig into local wine-making traditions—like the Chianti Half-day Wine Tour in the Tuscan’s Hills from Pisa, which combines picturesque scenery with tasting organic wines and olive oils. Others, such as the San Gimignano and Winery Experience with Light Lunch, give you a full day out with cultural highlights and regional flavors. With options ranging from quick tastings to full-day explorations with gourmet lunches, there’s something for every wine lover.
Here’s a quick summary of the types of tours you’ll find:
– Half-day winery visits with tastings and local foods, perfect for a quick wine fix (example 1).
– Guided tours of Pisa’s iconic monuments combined with wine tastings, ideal for culture and flavor in one go (example 2).
– Full-day excursions to San Gimignano and Chianti wineries, offering a deeper dive into Tuscany’s wine-making roots (example 4).
– Specialized experiences like authentic dinners with a sommelier or learning to make pasta with wine for a hands-on taste of Tuscany’s lifestyle.
Now, let’s explore each of these fantastic options in detail.
1. Chianti Half-day Wine Tour in the Tuscan’s Hills from Pisa
Starting with a true classic, this half-day tour whisks you from Pisa into the heart of Chianti’s vineyards. It’s perfect if you want a taste of Tuscany without sacrificing your entire afternoon. The trip includes visits to a family-run winery focused on organic wine-making methods, where you’ll explore the vineyard and cellar. You’ll sample local wines including Chianti red, along with olive oil, cheeses, and ham—all served in a relaxed, friendly setting. The small group size ensures personal attention, making it easy to ask questions and learn about traditional processes firsthand from the passionate producers.
What’s special? The vineyard visit offers a chance to see grapes growing on picturesque hills, weather permitting. Guests frequently comment on the fabulous views and the informative guides. One reviewer said Adriano’s commentary made the experience both fun and educational.
Bottom line: For around $103, you get a well-rounded experience that combines scenic beauty, authentic tasting, and cultural insight, making this top pick for a quick but meaningful Tuscan wine adventure.
2. From Pisa or Lucca: Half-Day Tuscany Chianti Wine Tasting
Next on our list, this 4-hour tour offers a chance to explore Tuscany’s rolling hills and meet a local winery owner. It’s ideal if you prefer a more flexible, intimate experience that emphasizes learning about organic wine production. The itinerary features a visit to a countryside winery, where you’ll sample the region’s signature wines, perhaps paired with local delicacies. The tour’s small-group format allows for a more personalized experience—perfect for those who want to ask lots of questions or just savor the scenery.
Guests often appreciate the knowledgeable guides and the chance to get up close with the winemakers themselves. One reviewer highlighted that the winery visit and tasting were excellent, with the opportunity to learn about production techniques and sample well-crafted wines.
Bottom line: At a slightly shorter duration and competitive price, this tour offers a rich taste of Tuscany’s wine culture with the added bonus of flexible options and small-group intimacy.
3. Pisa: Cathedral Guided Tour and Tower tickets & wine tasting
This combo experience is perfect if you want to combine Pisa’s iconic sights with a small-group wine tasting. Starting at the Piazza dei Miracoli, a licensed guide will walk you through the Cathedral, Baptistery, and Leaning Tower, with skip-the-line tickets available for climbing the tower (see details). After soaking in the views and learning about Pisa’s architecture and history, you’ll head to a nearby venue for a guided wine tasting featuring three Tuscan reds paired with cheeses and crostini.
Guests appreciate the personalized attention—the tour is capped at 15 people, and headsets help everyone hear the guide’s commentary. Reviewers note that Andrea’s knowledge makes the experience both fun and informative, and it’s a great way to enjoy Pisa’s highlights without feeling rushed.
Bottom line: Ideal for history lovers wanting a combined cultural and culinary experience in just 2.5 hours, with the added option of climbing the famous tower.
4. San Gimignano and Winery Experience with Light Lunch from Pisa
For those seeking a full-day adventure, this tour offers a combo of medieval charm and wine. Starting early from Pisa, you’ll visit San Gimignano, a UNESCO World Heritage Site with its famous medieval towers. Spend about 2 hours wandering the streets, exploring shops, and soaking up history. Then, the tour continues to a Chianti winery where you’ll enjoy a tutored tasting paired with a light lunch. This experience gives a well-rounded glimpse into Tuscan culture, architecture, and winemaking.
What makes this tour stand out? The small-group size and the chance to try wines served at Michelin-starred restaurants, along with regional cheeses and oils. Reviewers consistently praise the friendly guides and the balance of sightseeing and tasting. One noted that the guide Massimo made the day special.
Bottom line: Perfect for those wanting a comprehensive day trip that combines cultural exploration with wine and food.
5. Pisa guided tour and Wine tasting with Leaning Tower ticket (option)
This 2-hour guided walking tour offers a deep dive into Pisa’s landmarks with the chance to climb the Leaning Tower (if you choose). The guide will share fun facts and stories about Piazza dei Miracoli’s monuments before ending with a wine tasting featuring three Tuscan reds paired with local cheeses and crostini (see more).
Guests enjoy the compact, informative format, especially those who want a taste of history and local flavors in a short period. The optional tower climb is a big bonus, though some find it a bit rushed.
Bottom line: Excellent for travelers who want a quick yet rich overview of Pisa’s highlights combined with wine.
6. Authentic Full dinner & Wine Experience with a Sommelier in Pisa
If you’re after an evening of genuine Tuscan flavors, this full dinner experience delivered by a friendly sommelier is hard to beat. Over about 3 hours, you’ll enjoy over 15 authentic products—from family farm cheeses to regional wines, charcuterie, pizza, and gelato—across four different locations. The guide shares insider insights into Tuscany’s wine and food traditions, making it both delicious and educational.
One reviewer appreciated how Ariela “made us feel at home” despite the last-minute travel chaos caused by train strikes. The tour is limited in size for a more personal experience that feels like a dinner among friends.
Bottom line: Best suited for travelers craving a gastronomic immersion—a perfect end to a day exploring Pisa or Tuscany.
7. Tuscan Wine Tour in Pisa by van
This 6-hour tour dives deeper into wine production, starting with a visit to a hidden 18th-century wine cellar. Led by the vintner himself, you’ll see vineyard grounds, bottling rooms, and taste wines served at Michelin-starred restaurants. The experience emphasizes behind-the-scenes access, making it ideal for those who want a more immersive look at Tuscany’s wine culture.
Guests praise the personalized tour style and the delicious wines they sampled. One reviewer said it’s a great way to escape the tourist trail and learn what makes Tuscan wines special.
Bottom line: Perfect for serious wine enthusiasts wanting an intimate, detailed look at production and regional flavors.
8. Wine Tasting with Local Bites in Pisa near the Tower
For a quick, relaxed taste, this one-hour wine tasting in Pisa offers four wines paired with local cold cuts and cheeses. Located in a charming wine “warehouse” bar close to the Leaning Tower, it’s a great way to unwind after sightseeing.
Many reviewers enjoy the friendly service and knowledgeable staff who share insights about each wine. The pairings are well thought out, and the atmosphere feels authentic and inviting.
Bottom line: Best for travelers who want a casual, local experience with quality wines and good bites without a long commitment.
9. Learn the art of fresh pasta in the real heart of Pisa + Wine
Combine Italy’s two greatest passions—pasta and wine—with this 3-hour cooking class in Pisa. You’ll learn to make two types of fresh pasta in an atmospheric setting at the oldest hotel in Italy. The class includes a tasting of local wine and regional delicacies. It’s perfect if you want to get hands-on and leave with new skills and authentic recipes.
Reviewers note Claudio’s enthusiastic teaching style and the intimate setting make this a memorable experience. It’s great for foodies and families alike.
Bottom line: Ideal for those who want a fun, practical way to connect with Tuscany’s culinary traditions.
10. Pisa: Winery Tour and Wine Tasting with Local Food Pairing
This short but sweet 2-hour tour offers a guided winery visit with tastings of three wines paired with local foods. It’s a good option for travelers on a tighter schedule who want a taste of regional flavors without sacrificing too much time. The wines include IGT Costa Toscana Rosso 2022 and Merlot, making it a solid choice for those interested in varietals.
Though the reviews are mixed, the overall impression is that it provides a decent introduction to Tuscany’s wine culture.
Bottom line: Suitable for a quick palate-pleasing experience especially if you’re nearby and short on time.
11. Chianni: wine and oil tasting with lunch or dinner
For a full meal with wine, this tour offers a tasting of four Tuscan wines along with organic extra virgin olive oil and a lunch or dinner. It’s a flavorful way to enjoy local products in a relaxed setting, perfect for foodies who want to dive into Tuscan flavors. Reviewers note that the food and wine pairing is authentic and generous, and the experience is both educational and delicious.
Ideal for those who want to combine gastronomy with wine in an immersive experience.
Bottom line: A solid choice for food lovers seeking a comprehensive tasting and meal.
12. Soiana: Vineyard & Cellar Tour with Wine Tasting near Pisa
Finally, this family-run winery offers an intimate tour through vineyards and cellar, culminating in a tasting of five wines paired with bread and bruschetta. The guided visits give insight into both traditional and innovative winemaking.
Guests frequently mention the friendly hosts and the quality of the wines, making it a top pick for those wanting a personal touch in their wine experience. The tour lasts about 1.5 hours, making it perfect for a short but meaningful visit.
Bottom line: Excellent for wine lovers who prefer personal stories and authentic tastes straight from the producers.
How to Choose Your Ideal Wine Tour in Pisa
Picking the right experience depends on your schedule, interests, and budget. If you want a quick taste of Tuscany with stunning scenery, the Chianti Half-day Wine Tour offers excellent value. For a cultural combo, the Pisa Cathedral, Tower, and Wine Tasting provides a compact dose of Pisa’s iconic sights alongside local flavors. Those craving a full day of exploration should consider the San Gimignano and Winery Experience, which combines history, scenery, and wine in one seamless trip.
Budget-conscious travelers might prefer shorter experiences like the Pisa Wine Tasting with Bites, while foodies and connoisseurs will appreciate the Authentic Dinner & Wine Experience. Always book early, especially for popular tours, and consider your fitness level—some tours involve walking or climbing, like the Tower.
Final Thoughts
Pisa offers a surprising variety of wine-related experiences that will satisfy most tastes and schedules. For a quick introduction to Chianti wines, the half-day winery tour is hard to beat. If you prefer more immersion, the full-day San Gimignano and winery trip provides a lovely blend of sightseeing and tasting. For those seeking a culinary adventure, the full dinner with a sommelier promises an authentic and delicious evening.
Whatever your choice, remember that booking in advance ensures availability, and many tours offer flexible cancellation policies. Whether you’re a casual sipper or a serious enthusiast, Pisa’s wine tours are an excellent way to deepen your appreciation of Tuscany’s rich flavors—so don’t delay, raise your glass, and enjoy the journey.
