“Ramble Through The Rolling Hills Of Chianti” with lunch & Wine Tastings

Ramble Through The Rolling Hills Of Chianti with lunch & Wine Tastings

Imagine a day spent wandering among cypress-lined roads, lush vineyards, and medieval villages—that’s exactly what this private tour offers. Starting from Pisa, for about 8 hours, you’ll explore iconic sights like San Gimignano, taste delicious Tuscan food, and savor some of Italy’s best wines.

What we love most is the chance to experience authentic local flavors with a homemade pasta lunch paired with a variety of wines, along with expert-guided tastings at family-run wineries. Plus, the views of Tuscany’s famous medieval towers and rolling hills are truly breathtaking.

One thing to keep in mind is that this tour is quite full and involves a fair amount of driving, which might be a consideration if you’re sensitive to long bus rides. Still, it’s perfect for those who want a comprehensive, insiders’ look at Chianti’s wine, food, and history—all in one day.

This experience suits wine enthusiasts, history lovers, or anyone eager to see Tuscany beyond the usual tourist spots. If you enjoy learning from passionate guides and tasting local specialties in a relaxed setting, this tour is a winner.

This experience made our article of The 5 Top Lunch Experiences In Pisa: Which Is Best?.

Key Points

• Authentic Experience: Enjoy a genuine taste of Tuscany’s food and wine from family-run farms and cellars.
• Expert Guides: Knowledgeable guides like Andrea enhance the day with stories and insights.
• Stunning Scenery: Pass through beautiful landscapes full of vineyards, olive groves, and medieval towers.
• Cultural Highlights: Visit the medieval hilltop town of San Gimignano, famous for its towers and Vernaccia wine.
• Tasty Meals & Tastings: Savor a homemade pasta lunch paired with multiple wine tastings, including Chianti, Sangiovese, and Super Tuscan.
• Flexible & Private: The tour is private, with pickup from your Pisa accommodation, ensuring a personalized experience.

A Detailed Look at the Tour Experience

Starting with San Gimignano

Your day begins with a pickup at your hotel, B&B, or private apartment in Pisa. From there, your driver, such as Andrea in reviews, takes you on a scenic drive through Tuscany’s sigh-worthy landscapes—think rows of olive trees, lush vineyards, and cypress-lined roads. This part of the journey is as much about the views as it is about the anticipation of what’s to come.

The first stop is the medieval village of San Gimignano, often called the “Town of Fine Towers”. Once boasting over 70 towers, today fewer remain, but those that do create an almost fairy-tale skyline. The town is a UNESCO World Heritage site, and wandering its narrow, cobbled streets feels like stepping back in time.

You’ll love the sense of walking among history, with medieval walls, towers, and ancient piazzas. The reviews highlight how Andrea’s passion and knowledge make this visit particularly memorable—“a great village,” one reviewer notes, emphasizing the authentic experience.

While here, you’re free to explore at your own pace, perhaps popping into local artisan shops or enjoying some saffron or white Vernaccia wine, which the town proudly produces.

Scenic Drive Through Chianti’s Heartland

After your visit to San Gimignano, you’ll continue through what many call the “most beautiful wine road” in Tuscany. The drive itself is worth the journey—it’s lined with vineyards, olive groves, and picturesque farmhouses. This landscape is exactly what many travelers envision when dreaming of Tuscany.

The Farm and Lunch Experience

Next, you arrive at Podere La Marronaia- Le Colonne, a family-run, bio-dynamic farm. Here, you’ll step into the Tuscan countryside lifestyle. The setting is perfect for a relaxed, authentic meal, with options to sit in a lush garden or a cozy tasting room.

Lunch is a three-course affair featuring homemade pasta, bruschetta, Pecorino cheese, and cold cuts. As you eat, you’ll enjoy wine pairings including Chianti, Chianti Riserva, Sangiovese, and Vernaccia, as well as extra virgin olive oils, balsamic vinegar, and truffle oil tastings. This is a highlight for many, especially those who appreciate local food and wine.

One reviewer mentions how the quality of the food and wine made the experience truly special: “A beautiful Italian experience to learn the best combinations between wine & food.” The opportunity to taste small-batch, authentic products makes this meal stand out.

Final Stop at a Classic Chianti Winery

As afternoon approaches, it’s time for another wine experience at a traditional Chianti estate—likely a well-established winery like Poggio ai Laghi, Lornano, or Guidi. Here, you’ll learn about the history and production of the famous Chianti Classico, marked with the Black Rooster seal.

Expect a second tasting session, where you can savor the elegant, full-bodied flavors of Chianti and Super Tuscan wines. The reviews again praise the knowledgeable guides—“Andrea shared so much great information,” says one—and the opportunity to taste different wines helps you understand what makes Chianti so globally beloved.

Return Journey

After these tastings, your driver will take you back to Pisa, usually arriving around 5 pm, giving you a full day of sightseeing, eating, and drinking without feeling rushed.

What This Tour Means for You

Transportation & Logistics

The tour uses private, air-conditioned vehicles, ensuring comfort during the scenic drives. Pickup is from your accommodation, making logistics simple and stress-free. The total duration is about 8 hours, giving ample time to soak in the sights without feeling overwhelmed.

Value and Inclusions

At $289.40 per person, this tour offers a significant amount of value, especially considering the two wine tastings, a three-course lunch, and visits to two distinct wineries. The inclusion of bottled water, expert driver, and private transportation adds convenience to the experience.

Authenticity & Personal Touch

What sets this tour apart is its focus on local, family-run farms and wineries. The reviews highlight the guides’ passion and knowledge, which elevate the experience from a typical group tour to a more personalized visit.

For Whom Is This Best?

If you crave authentic Tuscan food and wine, love historical towns, or want to learn directly from passionate locals, this tour hits the mark. It’s especially suited for wine lovers, history buffs, or anyone who enjoys scenic drives and charming villages.

Final Thoughts

This private Chianti day trip offers a well-rounded, immersive experience in the Tuscan countryside. You’ll visit the medieval towers of San Gimignano, taste home-cooked pasta paired with premium wines, and explore a traditional Chianti estate—all with expert guides making the journey informative and enjoyable.

For those wanting a balanced mix of sightseeing, food, and wine, it’s hard to beat the combination of authentic charm, stunning scenery, and culinary delights packed into one day. The tour’s private nature ensures a tailored experience, ideal for travelers who value comfort, flexibility, and genuine local insights.

Keep in mind, the day is quite busy, and some may find the driving a bit long, but the payoff is a true taste of Tuscany’s heritage and flavors. This experience offers excellent value for those eager to explore Italy’s famous wine region in a relaxed, authentic manner.

FAQ

Is this tour suitable for families or children?
Yes, most travelers can participate, and since it’s a private tour, it can be tailored for families. Just consider the long driving hours and meal portions for younger children.

What is included in the price?
The price covers private transportation, two wine tastings at different wineries, a three-course Tuscan lunch, bottled water, and expert guidance throughout the day.

How many wineries will we visit?
You’ll visit two wineries: one family-run farm with a lunch and tasting, and a second traditional Chianti estate for a second tasting.

What kind of wines will we taste?
Expect to sample Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Super Tuscan wines.

Can I customize the stops or itinerary?
Since this is a private tour, there’s flexibility to discuss your preferences with your guide, but the core itinerary is designed to showcase the best of Chianti.

What time does the tour start?
The tour begins at 9:00 am, with pickup from your Pisa accommodation.

This detailed, authentic day in Tuscany promises a perfect blend of scenic beauty, historical charm, and flavorful experiences—ideal for those looking to truly taste and see the heart of Chianti.