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

A Taste of Tuscany: The “Sweet Hills of Chianti and San Gimignano” Private Tour

Imagine a day where you get to explore medieval San Gimignano, drive through the famously beautiful Chianti hills, and visit two different wineries. All of this is possible on the private “Sweet Hills of Chianti and San Gimignano” tour, priced at around $288 per person, lasting about 8 hours. Your experience begins with a personal driver who picks you up from your accommodations in Pisa, saving you the hassle of navigating busy streets or organizing transportation. The day is packed with stunning scenery, historic towns, and wine tastings that promise to satisfy your senses.

What we love about this tour is how it balances authentic Tuscan charm with convenience. First, the dedicated driver means you won’t waste precious time figuring out public transport or worrying about directions. Second, the self-guided exploration of San Gimignano allows you to soak in the medieval ambiance at your own pace — a rare luxury in guided tours. However, keep in mind that this tour does not include a professional guide, so if you’re craving detailed historical commentary, you might want to prepare some background info beforehand. This experience suits travelers who want a seamless, immersive taste of Tuscany without the crowds or complicated logistics.

Key Points

• Private transportation ensures a relaxed, flexible day with your own driver.
• Self-guided time in San Gimignano offers freedom to explore at your own pace.
• Authentic Tuscan lunch paired with six wines provides excellent value.
• Multiple wine tastings showcase the region’s renowned Chianti wines.
• The tour combines scenic drives with cultural visits, making it a well-rounded experience.
• Suitable for most travelers, especially those wanting comfort and flexibility without sacrificing authenticity.

An In-Depth Look at the “Sweet Hills of Chianti and San Gimignano” Tour

Starting the Day: From Pisa to the Tuscan Hills

Your adventure kicks off bright and early at 8:30 am, when your personal driver will come to pick you up from your hotel, B&B, or private apartment in Pisa. From there, it’s a short drive into the heart of Tuscany’s famous rolling hills, a landscape marked by olive groves, cypress trees, and vineyards. The scenery alone justifies the journey — you’ll see why Tuscany’s landscapes have inspired painters and writers for centuries.

First Stop: San Gimignano — The Medieval Skyscraper Town

Your first destination is San Gimignano, often called the “City of Beautiful Towers”. It’s renowned for its skyline of medieval towers that have survived since the 12th century, giving travelers a fairy-tale feel. With about an hour for self-guided exploration, you can wander through narrow stone streets, visit historic churches, browse charming shops, and indulge in a scoop of the famous gelato from Gelateria Dondoli, a two-time world champion.

Our experience aligns with reviews praising this stop for its stunning architecture and atmospheric charm. One traveler noted, “We loved the way you can explore at your own pace, and the gelato is truly the best in the world.” It’s a perfect introduction to Tuscany’s medieval heritage and a chance to sample Vernaccia di San Gimignano, a local white wine that pairs beautifully with the town’s culinary offerings.

Scenic Drive Through Chianti’s Iconic Landscape

After your time in San Gimignano, you’ll hop into the vehicle to cruise through one of Tuscany’s most picturesque routes. The drive takes you along the famous Chianti wine road, where olive groves and vineyards stretch as far as the eye can see. This stretch is worth it just for the views, but it’s also a window into the region’s agricultural traditions that have shaped its identity.

Lunch at Podere La Marronaia- Le Colonne: A Farm-to-Table Experience

Next, you’ll arrive at Podere La Marronaia, a family-run organic farm offering a delicious Tuscan feast. The lunch is a highlight, with homemade pasta, bruschetta, cured meats, and pecorino cheese, all served with a selection of six wines including Chianti, Chianti Riserva, and Vernaccia. The meal is complemented by tastings of extra virgin olive oils, balsamic vinegar, and even truffle oil.

Reviewers rave about this stop for its authenticity and delicious food. One said, “The farm’s view of San Gimignano with its medieval towers is breathtaking, and the food was like a home-cooked feast.” The farm’s breathtaking panoramic views create a sense of genuine Tuscan life that’s often missing in larger, commercial experiences.

Exploring Monteriggioni — The Fortress Town

Post-lunch, your driver takes you to Monteriggioni, a tiny fortress town founded in the early 13th century. The medieval castle was built as an outpost against Florence and remains remarkably intact. Inside, you can visit a small museum of medieval weapons and walk along the city walls, taking in views of the countryside.

This spot gets praise for its authentic medieval atmosphere and imposing fortifications. As one reviewer commented, “Walking around Monteriggioni feels like stepping back in time, and the castle’s history is palpable.”

Final Stop: Chianti Classico Winery

The day wraps up with a visit to a Chianti Classico winery, where you’ll enjoy your second wine tasting session. This part of the tour is especially appealing for wine lovers, as you’ll sample the “Gallo Nero”—the iconic symbol of Chianti Classico wines—and learn about winemaking traditions. The winery’s long history and hands-on approach ensure you get a taste of genuine Tuscan wine craftsmanship.

Returning to Pisa

After the winery visit, your driver will take you back to Pisa, usually arriving before sunset. The convenience of private transport means you can relax and reflect on the day’s highlights without the stress of navigating.

Who Will Love This Tour?

This experience is ideal for travelers who want a comprehensive, easy-to-join day trip from Pisa, combining cultural sights, gourmet food, and excellent wines. If you prefer to explore at your own pace and value authentic local experiences over large tour groups, this private tour hits the mark. It’s particularly well-suited for couples, small groups, or anyone who appreciates scenic drives, medieval towns, and delicious Tuscan cuisine.

Pricing and Value

At $288.10 per person, this tour offers a good balance between luxury and value. The inclusion of private transportation, lunch with wine, and multiple tastings makes it a comprehensive package. Without the need for a guide, you’re free to explore at your own pace, making it a flexible option for those who enjoy a personalized experience. The reviews reinforce this value, with travelers praising the knowledgeable guides and delicious food, noting that they felt they received a lot for the price.

Final Thoughts

This private tour is best for those who want a relaxed, authentic Tuscan experience without the hassle of organizing logistics. The combination of beautiful scenery, medieval towns, and wine tastings makes it a memorable day for lovers of history, food, and wine. The self-guided exploration in San Gimignano gives you freedom, while the lunch and winery visits add depth and flavor to the trip.

If you’re looking for a well-organized, value-packed day that immerses you in the heart of Tuscany’s landscape and culture, this tour will deliver. Just be prepared for a full day of sightseeing and indulgence, and you’ll come away with plenty of stories and, of course, some excellent bottles of Chianti.

FAQ

Is this tour suitable for all ages?
Yes, most travelers can participate, as it’s designed for comfort and flexibility. It’s a full day, so bring comfortable shoes and be prepared for some walking.

Are meals included?
Yes, you’ll enjoy a three-course lunch with homemade Tuscan dishes paired with six wines. The meal features pasta, cured meats, cheese, and more.

How many wineries will I visit?
You’ll visit two different farm wineries for tastings, and there’s also a visit to a Chianti Classico winery later in the day.

Is a guide provided during the stops?
No, this is a self-guided experience at San Gimignano and during your lunch. However, your driver is knowledgeable and can share insights.

Can I customize the itinerary?
The tour is private, so you may discuss with the operator if you wish to adjust the stops or timing.

What’s the best time to book?
Most travelers book about 49 days in advance; mornings tend to be cooler and more comfortable for sightseeing.

How long is the drive between stops?
The drives are scenic and typically short, giving you plenty of time to enjoy the views and relax.

Is transportation air-conditioned?
Yes, your private vehicle is air-conditioned, ensuring comfort throughout the day.

Can I bring snacks or extra drinks?
Food and drinks are provided during lunch and tastings, so outside snacks are usually unnecessary but can be brought if preferred.

What should I wear?
Comfortable shoes for walking, sun protection, and layered clothing are recommended, especially if visiting in warmer months.

To sum it up, this private Chianti and San Gimignano tour offers an authentic slice of Tuscany’s landscape, history, and wine culture, all with the comfort of personalized service. Whether you’re a history buff, a foodie, or a wine lover, it delivers a well-rounded, scenic, and delicious day out — perfect for those wanting to experience Tuscany without the crowds.