PRIVATE TOUR “Sweet Hills of Chianti and San Gimignano” with Lunch & 2 Tastings

Exploring Tuscany’s rolling hills doesn’t have to be complicated. This private tour from Pisa promises a smooth, personalized way to soak up the region’s most iconic sights, flavors, and history—all in a single day. With a dedicated driver, flexible stops, and thoughtfully curated experiences, it offers a well-balanced taste of what makes Tuscany special.

What we love about this tour:

• The convenience of a private driver making logistics effortless.
• The opportunity to explore two enchanting medieval towns at your own pace.
• The delicious, authentic Tuscan lunch with wine pairings that elevate the experience.
• The chance to visit two wineries, tasting Chianti and other regional wines directly from local producers.

A possible consideration:
The day is packed and involves a fair amount of driving, so it might feel a bit rushed if you prefer more leisurely, in-depth exploration. Also, the tour’s price reflects its private nature, which might be on the higher side for some travelers.

Who is this for:
This experience suits travelers looking for a full-day, curated immersion into Tuscany’s landscapes, towns, and wines without the hassle of planning. It’s perfect for those who prefer comfort, local authenticity, and a flexible itinerary.

Key Points:

• Private transportation ensures comfort and efficiency.
• Self-guided exploration in San Gimignano allows for personalized discovery.
• Tastings at two wineries showcase regional varieties like Chianti and Vernaccia.
• Authentic Tuscan lunch with regional specialties and wine.
• Visit historic sites like Monteriggioni Castle and learn about medieval defenses.
• Expert guides and drivers add local insights and smooth the day.

An In-Depth Look at the Chianti & San Gimignano Experience

Starting Your Day in Pisa with Private Pickup

The tour kicks off early at 8:30 am with a private, air-conditioned vehicle ready to whisk you away from your Pisa accommodation. Having your own driver, as noted by reviewers like Michael F., “made the day so special,” sharing not just the logistics but also tidbits of regional history and culture. This personalized approach means you won’t be stuck with strangers, allowing for a relaxed atmosphere and flexible pacing.

Exploring San Gimignano: Medieval Marvels and Gelato

Your first stop is San Gimignano, often called the “Town of Beautiful Towers”—a nickname well-earned by its skyline of medieval bell towers. The town’s narrow streets, historic churches, and charming shops make it a favorite for visitors. The self-guided exploration means you can linger over sights like the main square or the ancient walls, soaking up the town’s timeless atmosphere.

One standout feature here is the gelato. Thanks to Gelateria Dondoli, a two-time world champion, you can indulge in some of the best gelato in the world. Reviewers mention that this is a must-try, and it’s easy to see why—creamy, inventive flavors that cap off your visit to this fairy-tale town.

Along With its sweet treats, San Gimignano is renowned for its saffron, Prosciutto d’Oro, and Vernaccia di San Gimignano wine. The town’s wine, made from ancient local grapes, pairs beautifully with the region’s cuisine and provides a taste of its storied viticultural traditions.

Scenic Drive Through the Chianti Hills

Leaving San Gimignano, your journey continues through one of Tuscany’s most famous landscapes. The wine road winds through gentle hills dotted with olive groves, cypress trees, and vineyards. This drive alone is worth the trip—reviewers like Scott B. appreciated the “beautiful wine road in Tuscany” and noted that their driver, Mario, was “very knowledgeable about the area.” The scenery is quintessential Tuscany, with picture-perfect views at every turn.

Lunch at Podere La Marronaia: A Tuscan Farmhouse Feast

At Podere La Marronaia, a family-run organic farm, you’ll enjoy a three-course Tuscan meal. The food is aligned with what reviewers describe as a “traditional Tuscan feast”—think bruschetta, homemade pasta (lasagna or similar), cured meats, Pecorino cheese, and delicious desserts. Authenticity and freshness are the key here, along with the farm’s breathtaking views of San Gimignano’s towers.

The lunch also features wines: Chianti, Chianti Riserva, Sangiovese, and Vernaccia. Tasting multiple wines from the region allows you to appreciate the subtle differences and craftsmanship that go into each bottle. Accompanying oils like extra virgin olive oil, pepper olive oil, balsamic vinegar, and truffle oil bring out the flavors of your meal, making it a true sensory experience.

Medieval Monteriggioni: A Fortress of the Past

Post-lunch, your next stop is the medieval fortress of Monteriggioni. Founded between 1213 and 1219, this walled town was built as a defensive outpost against Florence. Inside, you can visit the medieval weapons museum, giving a glimpse into the town’s military history. The short 30-minute stop allows you to walk its ramparts and imagine what life was like in medieval times.

A reviewer mentions how Monteriggioni’s “impregnable fortress” still evokes the old-world charm, and the compact size means it’s perfect for a quick visit that leaves you feeling transported back centuries.

Afternoon at a Chianti Classico Winery: Savoring the Gallo Nero

The final stop of the day is at Fattoria Lornano or a similar Chianti Classico winery, where you’ll experience the “king of wines”, Chianti Classico. This 45-minute tasting includes the iconic Gallo Nero (Black Rooster) label, and you’ll learn about the region’s winemaking traditions.

Guests like Michael F. appreciated the “knowledgeable guides” and the chance to sample a diverse selection of wines—from Chianti Riserva to Super Tuscans—directly from the producers. The relaxed tasting atmosphere allows you to savor the wines and ask questions about how they’re made, adding educational value to the experience.

Wrapping Up and Returning to Pisa

After a full day of sightseeing, eating, and tasting, your private driver will return you to your Pisa accommodation around 5:30 pm. The convenience of door-to-door service is highly valued, especially after a day of sensory overload.

Why This Tour Offers Great Value

When you consider the price of $288.10 per person, it covers a lot: private transportation, expert driver, guided visits, multiple tastings, and a hearty lunch. The combination of logistical ease and authentic experiences makes it a standout choice for travelers who want to truly enjoy Tuscany without the fuss of planning every detail.

The tour’s reviews emphasize the quality of guides and drivers, like Andrea and Mario, who make the day informative and fun. The small group or private format ensures a more personalized experience and flexibility in how you spend your time.

Who Should Consider This Tour?

This experience is ideal for couples, small groups, or solo travelers seeking a curated day in Tuscany with minimal hassle. Food and wine lovers will appreciate the tastings and farm-to-table lunch, while history buffs will enjoy exploring medieval towns and castles. If you want a comprehensive, comfortable taste of Chianti’s highlights in one day, this tour fits the bill perfectly.

Frequently Asked Questions

What is included in the tour?
The tour includes private transportation, two wine tastings at different wineries, a three-course lunch with regional wines, bottled water, and pickup from your Pisa accommodation.

Can I request a guide?
A guide isn’t included by default but can be arranged with a one-week notice and a surcharge.

What are the stops during the day?
Stops include San Gimignano, Podere La Marronaia farm for lunch and tastings, Monteriggioni Castle, and a Chianti Classico winery.

How long do we stay at each stop?
San Gimignano is about an hour for self-guided exploration, lunch lasts around 1.5 hours, Monteriggioni is approximately 30 minutes, and winery visits are about 45 minutes each.

Is this tour suitable for children?
Most travelers can participate, but the focus on wine tastings and medieval history may be more appealing for adults.

What is the pickup time?
Pickups are scheduled for 8:30 am from your Pisa hotel or residence.

How long does the tour last?
The tour is approximately 8 hours, returning around 5:30 pm.

What if I want to cancel?
You can cancel for free up to 24 hours in advance for a full refund.

Are the wines tasted included in the price?
Yes, two tastings at different farm wineries are included, featuring Chianti, Vernaccia, and Super Tuscan wines.

Is this tour a good value?
Given the private transport, high-quality tastings, and authentic meals, many find this tour offers excellent value for a full-day guided experience in Tuscany.

To sum it up, if you’re after a day that combines scenic beauty, culinary delights, and historical charm—all with ease and comfort—this private Chianti and San Gimignano tour ticks all the boxes. It’s especially suited for those who want a personalized journey without the stress of planning or navigating on their own. Whether you’re a wine enthusiast, history buff, or simply looking to experience Tuscany’s signature towns and tastes, this could become a highlight of your trip.