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

There’s something undeniably magical about Tuscany—its rolling hills, medieval towns, and world-class wines evoke a sense of timeless beauty. This private tour from Pisa promises to condense that magic into a single day, taking you through some of the region’s most iconic sights and flavors. It’s designed for those who want a seamless, personalized experience without the hassle of planning every detail themselves.

We love how this trip carefully balances sightseeing, tasting, and relaxation, all wrapped up with the comfort of private transportation. The inclusion of a dedicated driver means you can truly enjoy the sights without the stress of navigation or timetables. But, of course, with a full day packed with stops, it’s a fairly intensive experience—so be prepared for a busy, yet incredibly rewarding, day.

A potential consideration might be the price, which sits around $288 per person. While that’s a significant investment, the value is amplified by the personalized service, quality tastings, and authentic Tuscan meals included. This tour is best for travelers who crave a relaxed, yet comprehensive, taste of Tuscany’s highlights—perfect for those who want to see a lot without the hassle.

Who Would Love This?

If you’re a lover of good wine, charming towns, and authentic Italian cuisine, this tour hits all the right notes. It’s especially ideal for first-timers to Tuscany who want a curated experience with local insights, or for couples and small groups seeking a private getaway filled with memorable moments.

Key Points

• Private transportation ensures comfort and allows you to enjoy the scenery without stress.
• Flexible sightseeing at San Gimignano and Monteriggioni gives you time to explore at your own pace.
• Authentic Tuscan lunch paired with six wines offers a true taste of regional flavors.
• Two wine tastings at different wineries deepen your appreciation of Chianti’s variety.
• Guided insights from knowledgeable drivers enrich your understanding of Tuscany’s history and culture.
• Stunning landscapes of olive groves, cypress trees, and medieval towers create picture-perfect moments.

An In-Depth Look at the Itinerary

San Gimignano: The Towered Jewel of Tuscany

The journey kicks off with a pickup from your accommodation, setting the tone for a day of effortless exploration. Your driver, Andrea (as noted in reviews), is praised for sharing engaging stories and making the day feel personalized. With about an hour allocated, you’ll get plenty of time to wander this UNESCO-listed town.

San Gimignano is famed for its medieval towers, which rise dramatically above the narrow streets and give the town its nickname, the “City of Beautiful Towers.” Visitors often find themselves lost in its charming alleyways, lined with boutique shops, historic churches, and cafes. Reviewers have particularly raved about the gelato from Gelateria Dondoli, a two-time world champion, which is a must-try when in town.

What makes this stop shine is not just the scenery but the atmosphere—an authentic step back into Italy’s medieval past. The reviewers appreciated the self-guided approach, which allows for spontaneous discoveries and leisurely strolls.

Driving Through the Chianti Hills: The Scenic Route

Next, expect a scenic drive along one of Tuscany’s most picturesque roads, winding through olive groves and vineyards. This part of the trip offers breathtaking views that make every photograph feel like a postcard. It’s a treat for anyone who loves nature and landscape photography.

Lunch at Podere La Marronaia: A Tuscan Farm Feast

The highlight for many is the lunch stop at Podere La Marronaia, a biodynamic farm run by a friendly local family. Here, you’ll indulge in a three-course Tuscan meal, featuring homemade pasta, bruschetta, cured meats, pecorino cheese, and more—each dish bursting with traditional flavors. The meal is paired with six different wines, including Chianti, Chianti Riserva, Sangiovese, and Vernaccia.

Reviewers have described this as “an authentic Tuscan feast,” with some noting the breathtaking views of San Gimignano from the farm—truly a picture-perfect setting. Alongside the food, you’ll taste various oils, balsamic vinegar, and truffle oil, adding layers of flavor to the experience.

This stop isn’t just about eating and drinking; it’s also about learning. The hosts share insights into Tuscan winemaking and culinary traditions, making each sip and bite more meaningful.

Monteriggioni: A Fortress Frozen in Time

Post-lunch, you’ll visit the medieval fortress of Monteriggioni, founded between 1213 and 1219. This tiny town packs a punch with its perfectly preserved medieval walls and towers. Walking through Monteriggioni feels like stepping into a fairy tale, and the castle’s museum of medieval weapons adds a fun, tactile element to your visit.

Reviews highlight that the short stop here is a highlight—an ideal spot for photos and a quick history lesson. The town’s fortress status made it a formidable outpost against invading forces, making it a fascinating peek into Tuscany’s turbulent past.

Chianti Winery Tour & Tasting: The Grand Finale

In the late afternoon, your tour concludes with a visit to a Chianti Classico winery, such as Fattoria Lornano, for another round of tastings. This is where you get to sample the famous Gallo Nero (Black Rooster) wine, renowned worldwide. The winery’s long-standing tradition of winemaking shines through in the quality of the wines, which reviewers describe as “delicious” and “authentic.”

Here, you’ll learn about the production process and sample several wines in a relaxed setting. The combination of beautiful winery views and excellent wines makes this a memorable way to end your day.

The Practicalities: Transport, Pricing, and Timing

The entire experience is designed to be smooth and convenient. The private vehicle is air-conditioned, making the roughly 8-hour day comfortable even in warmer months. The tour starts at 8:30 am, giving you plenty of time to soak in the sights without feeling rushed.

At $288.10 per person, this tour offers good value for a full day of guided sightseeing, tastings, and a delicious meal included. It’s well worth the cost for those who prefer a curated, hassle-free experience rather than navigating on your own.

While the tour is private, it can accommodate most travelers, and the group size remains small enough for a personalized feel. If you wish, a professional guide can be arranged for an extra fee—though many reviewers appreciated their driver’s local insights.

Authentic Experiences and Hidden Gems

One of the tour’s biggest strengths is its ability to blend cultural sights with authentic flavors. The hosts and guides share stories that bring the places to life—like the tale of San Gimignano’s saffron and prosciutto, or the history behind Monteriggioni’s formidable walls.

The lunch at Podere La Marronaia isn’t just a meal; it’s a chance to connect directly with a Tuscan family, savoring homemade recipes and regional wines. The tastings at two distinct wineries provide a layered understanding of Chianti’s diversity, from classic Sangiovese blends to more unique offerings.

Reviewers have praised the guides for their knowledge and friendliness. Andrea’s storytelling and Mario’s local expertise have made the experience more than just sightseeing—they’ve turned it into a memorable journey through Tuscany’s soul.

Final Thoughts

If you’re after an all-in-one day trip that covers the highlights of Tuscany’s picturesque hill towns, delicious food and wine, and historic sites, this tour checks all boxes. The private aspect ensures a relaxed pace and personalized attention, making it suitable for couples, small groups, or anyone who appreciates comfort and authenticity.

The combination of scenic drives, engaging history, and delicious culinary experiences makes this a comprehensive introduction to what Tuscany has to offer. While it’s a bit of an investment, the value is clear when you consider the convenience, quality tastings, and memorable sights included.

For travelers craving a full, relaxed immersion into Tuscany’s iconic landscapes and flavors—without the stress of planning—this tour offers a thoughtfully curated, authentic day out.

FAQ

Is pickup offered for this tour?
Yes, the tour includes pickup from your hotel, B&B, or private apartment in Pisa, ensuring a hassle-free start to your day.

What is the duration of the tour?
The tour lasts approximately 8 hours, giving you plenty of time to enjoy each stop without feeling rushed.

Are the wine tastings included in the price?
Yes, you’ll enjoy two tastings at different wineries, including a variety of Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Super Tuscans.

Can I customize the itinerary?
Since this is a private tour, the itinerary is flexible to some extent, allowing your driver to tailor the experience to your preferences.

What’s the best time of year to book this tour?
While the tour operates year-round, spring and early autumn tend to offer the best weather and scenery.

Is a guide included during the sightseeing stops?
The driver is a local expert with good knowledge of the region, but a dedicated guide can be arranged for an extra fee if you prefer more in-depth commentary.

Are children or non-drinkers welcome?
Absolutely. The tour is suitable for most travelers, and non-drinkers can participate in all tastings and enjoy the sightseeing at their own pace.

What should I wear or bring?
Comfortable shoes are recommended for walking around towns and castles. Don’t forget sun protection and a camera to capture the stunning views.

This private tour from Pisa offers a stellar blend of scenic views, historic towns, and authentic flavors. It’s an excellent choice for those wanting an immersive, relaxed, and personalized taste of Tuscany’s best.