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

Explore the Charm of Chianti and San Gimignano on a Private Day Trip from Pisa

This private tour offers an immersive experience of Tuscany’s most captivating sights, all in a single day. Priced at $288.10 per person, it includes hotel pickup, lunch, two wine tastings, and visits to the iconic San Gimignano and Monteriggioni. With a dedicated driver, the tour maximizes your time, allowing for a relaxed pace and personalized exploration, making it ideal for those who want to avoid busy group travel.

The tour’s 8-hour duration ensures a thorough taste of the region’s scenic beauty, historic towns, and renowned wineries. Its popularity, with bookings averaging 49 days in advance, reflects its value and appeal. While the trip is rich in wine, food, and culture, it is well-suited for those comfortable with a full day of sightseeing and walking in medieval towns.

Key Points

• Private driver and transportation streamline the day, saving hours on logistics.
• Visit San Gimignano, famous for its towers, gelato, and Vernaccia wine.
• Explore Monteriggioni, a nearly impregnable medieval fortress with a weapons museum.
• Lunch at an organic Tuscan farm includes homemade pasta and six wines.
• End the day with a Chianti Classico winery tour and tasting of the Gallo Nero.
• Total duration: approximately 8 hours with flexible sightseeing.

Starting the Day with San Gimignano’s Medieval Charm

The tour begins with hotel pickup in Pisa, around 8:30 am, with a comfortable and air-conditioned vehicle. Your dedicated driver, knowledgeable about the region, sets the tone for a relaxed day. The first stop is San Gimignano, a UNESCO World Heritage site and known as the City of Beautiful Towers.

Here, you enjoy a self-guided walk through its cobblestone streets, exploring historic churches, charming shops, and the distinctive skyline dotted with medieval towers. Don’t miss sampling the famed gelato at Gelateria Dondoli, a two-time world champion, and sampling Vernaccia di San Gimignano wine, made from ancient local grapes. The visit lasts about an hour, enough to appreciate the town’s unique atmosphere without feeling rushed.

Scenic Drive Through Chianti’s Rolling Hills

After San Gimignano, the tour takes you along one of Tuscany’s most scenic wine roads. Your driver navigates through Chianti’s gentle hills, with views of olive groves, cypress trees, and vineyards. The landscape’s peaceful beauty is a highlight, providing perfect photo opportunities and an authentic taste of Tuscany’s countryside.

This drive not only adds to the scenic appeal but also builds anticipation for the upcoming winery visit. The route showcases the region’s natural charm, making this part of the journey as memorable as the stops themselves.

Lunch at Podere La Marronaia- Le Colonne Biodynamic Winery

The next stop is at Podere La Marronaia- Le Colonne, a family-run organic farm set on a hillside overlooking San Gimignano’s towers. Here, the lunch is a classic Tuscan feast featuring bruschetta, homemade pasta such as lasagna, cured meats, pecorino cheese, and a delicious dessert.

Wine lovers will enjoy tasting five wines during the meal, including Chianti, Chianti Riserva, Sangiovese, and Vernaccia. Alongside the wines, you sample extra virgin olive oils, balsamic vinegar, and truffle oil, gaining insight into traditional Tuscan food and wine pairing techniques. The 1 hour 30-minute lunch offers a genuine farm-to-table experience amid breathtaking views of the medieval skyline.

Exploring the Fortress of Monteriggioni

Post-lunch, the tour continues to Monteriggioni, a nearly impregnable medieval castle built by the Sienese between 1213 and 1219 as a defensive outpost. Inside, visitors can explore the medieval weapons museum, which adds a historical dimension to the visit.

The castle’s 30-minute stop provides a chance to walk around the well-preserved ramparts and imagine medieval life. The fortress’s strategic importance and impressive walls make it a highlight for history buffs and photo enthusiasts alike.

Afternoon at a Chianti Classico Winery

As the day progresses, the tour visits Fattoria Lornano or a similar Chianti Classico winery like Guidi or Poggio ai Laghi. These wineries have long histories of wine production and offer an authentic taste of Chianti’s signature Gallo Nero red wine.

Here, a 45-minute tasting session introduces you to Chianti Classico, showcasing its bold flavors and aging potential. This final wine experience emphasizes the region’s dedication to quality, with free tastings included. The visit provides insight into the winemaking process and the heritage behind Italy’s most famous wine label.

End of the Day and Return to Pisa

After the last tasting, the private driver takes you back to your hotel or private residence in Pisa. The tour typically concludes around 5:30 pm, offering a full yet relaxed day of cultural sights, scenic drives, and wine experiences. The private transportation ensures comfort and flexibility, allowing you to enjoy Tuscany without the hassle of public transit or crowded group tours.

Exclusive Inclusions and Practical Details

This private tour includes air-conditioned vehicle, two wine tastings at different farm wineries, lunch with homemade dishes and six wines, and local expert driving. The lunch features a 3-course meal with homemade pasta, bruschetta, Tuscan ham, and Pecorino cheese, perfectly paired with wines and oils.

The tour departs from Pisa at 8:30 am, with hotel pickup arranged, and operates with group discounts available. The full-day experience is suitable for most travelers, with most participants able to participate comfortably.

Why Choose This Tour? The Perfect Blend of Culture, Food, and Wine

This private tour stands out because of its carefully curated stops, balancing historic towns, scenic drives, and wine tastings. The inclusion of a lunch at an organic farm enriches the experience, adding authenticity and flavor. The knowledgeable driver and flexible self-guided exploring time at San Gimignano and Monteriggioni make this a personalized and relaxed option.

The high ratings—both 5 out of 5—reflect the quality, with reviews praising the guides’ expertise and the wines’ authenticity. The famous gelato at San Gimignano and the amazing vineyard views further enhance its appeal.

Who Would Enjoy This Tuscany Day Trip?

This tour suits wine lovers, history enthusiasts, and those seeking a scenic escape from Pisa. It appeals to travelers who prefer a private, tailored experience with the convenience of hotel pickup and luxury transport. The combination of culinary delights and cultural exploration makes it perfect for couples, families, or small groups seeking an authentic Tuscan experience.

While the full day involves walking in towns and some uphill areas, the pace remains comfortable, thanks to the private driver and well-planned itinerary. It’s especially recommended for those wanting to maximize their time with delicious food, fine wines, and stunning views.

Frequently Asked Questions

What is included in the price of this tour?
The tour includes private transportation, hotel pickup, two wine tastings at different wineries, lunch with three courses and six wines, bottled water, and admission to Monteriggioni’s weapons museum.

How long does the tour last?
The total duration is approximately 8 hours, from 8:30 am pickup to return to Pisa around 5:30 pm.

Is this tour suitable for children or non-drinkers?
Yes, the tour is suitable for most travelers, and non-drinkers can enjoy the sightseeing and lunch options. The focus on wine tastings can be skipped if preferred.

Can I customize the stops or meals?
As a private tour, it offers flexibility, and any specific requests can be discussed with the provider, Pek Tuscany in Limo.

Is there a guide or just a driver?
The tour features a local expert driver who shares insights during transport but is not a dedicated guide. Guide services are available upon request for an additional fee.

What should I wear or bring?
Comfortable shoes for walking in towns and towns, sunscreen, and a camera are recommended. The vehicle is air-conditioned, and bottled water is provided.

Can I book this tour last-minute?
Advance bookings are recommended, with an average of 49 days in advance. Last-minute bookings are subject to availability.

What if I need to cancel?
Cancellation is free up to 24 hours before the tour, offering full refund if canceled within this window.

Is the tour accessible for people with mobility issues?
While the tour involves walking through medieval towns and castle ramparts, specific accessibility accommodations are not detailed; contact the provider for assistance.

How far in advance should I book?
Booking at least two months ahead is advisable to secure a spot, especially during peak seasons.

This private “Sweet Hills of Chianti and San Gimignano” tour offers a well-balanced day of Tuscan culture, cuisine, and wine, with personalized service and a relaxed pace. Perfect for those who want an authentic taste of Tuscany’s most enchanting sights without the hassle of group tours.