PRIVATE TOUR: Volterra & San Gimignano with Lunch & Wine Tasting Experience

Exploring Tuscany: A Private Day Trip to Volterra & San Gimignano with Lunch & Wine Tasting

If you’re craving an authentic taste of Tuscany—its rolling hills, historic towns, and delicious cuisine—this private tour hits all the right notes. For around seven hours, you’ll explore Volterra, a walled Etruscan city with Roman ruins and a captivating history, and San Gimignano, famed for its medieval towers that seem to reach for the sky. The tour, priced at about $232 per person, includes the convenience of pickup from your Florence accommodations, a leisurely lunch at a biodynamic winery farm, and a chance to sample some of Italy’s finest wines.

What we love most about this experience is how personalized it feels. With a private driver, you get ample time to soak in the sights without feeling rushed, and the inclusion of a local organic farm for lunch makes the meal both hearty and genuine. Plus, the wine tastings—which feature Chianti, Vernaccia, and more—offer a perfect pairing with the farm-fresh dishes.

One thing to consider is that, since this is a private tour, it’s mostly suited for those looking for a more intimate, flexible experience rather than a group hustle. If you’re interested in exploring Tuscany’s countryside and medieval towns in comfort, this tour offers excellent value. It’s especially ideal for travelers who appreciate authentic food, fine wines, and less touristy, more local experiences.

Key Points

Personalized Experience: The private nature ensures your itinerary adapts to your pace and interests.
Cultural & Historic Highlights: Discover Etruscan and Roman relics in Volterra, and medieval towers in San Gimignano.
Gourmet Food & Wine: Enjoy a genuine Tuscan lunch paired with five different wines, olive oils, and balsamic vinegar tastings.
Scenic Drives: Travel through the famous Chianti wine road and the rolling hills of Tuscany, with picturesque views at every turn.
Comfort & Convenience: Door-to-door pickup and air-conditioned transport make for an easy day.
Authentic Experiences: Visit a family-run organic farm, learn about local winemaking, and taste regional specialties.

A Closer Look at the Itinerary and What You Can Expect

Starting Point: Florence and the Drive into Tuscany

The journey begins with a pickup from your hotel or accommodation in Florence around 9:00 am. Your driver, who’s often praised for their friendly, knowledgeable attitude—as Debra mentioned, “Daniel was a great driver”—will whisk you out of the city and into the lush Tuscan countryside. Expect to pass through olive groves, vineyards, and fields of sunflowers, setting a peaceful tone for the day ahead.

This drive isn’t just transportation—it’s part of the experience, giving you your first glimpses of what makes Tuscany special: natural beauty, timeless landscapes, and classic imagery like cypress-lined roads.

First Stop: Volterra – An Etruscan and Roman Treasure

About an hour and a half from Florence, your first destination is Volterra. This small hilltop city is a treasure trove for lovers of history and architecture. Built over one of the Twelve Cities of the Etruscan civilization, the city still retains walls and gates from its ancient past. A self-guided visit allows you to explore at your own pace, which is a real benefit for those wanting to soak in the atmosphere without the rush.

Highlights include the Roman Theater—a well-preserved ruin that hints at the city’s importance during Roman times—and the octagonal Baptistery and Duomo, which showcase medieval religious architecture. The town’s narrow streets and atmospheric squares make it easy to imagine what life was like centuries ago.

Travelers who have been here say, “It was good to spend more time in Volterra than San Gimignano,” appreciating its less touristy charm and genuine historical feel. You might find the relics and archaeological sites fascinating, especially if you enjoy uncovering layers of history.

Midday: Lunch at Podere La Marronaia – Le Colonne Organic Farm and Winery

After exploring Volterra, you’ll head to a family-run organic farm for a true Tuscan lunch. This is more than just a meal; it’s an immersion into local food traditions. Expect a hearty spread of bruschetta, lasagna or fresh homemade pasta, cured meats, pecorino cheese, and perhaps a sweet treat.

What sets this lunch apart is the pairing with five wines including Chianti, Sangiovese, Brunello, and Vernaccia, along with tastings of extra virgin olive oils, balsamic vinegar, and truffle oil. It’s a chance to learn how regional ingredients and simple techniques create such distinctive flavors.

Guests consistently mention how delightful the experience is: “A delicious lunch in the Winery Farm + 5 Wine tasting,” along with the chance to learn about Tuscan winemaking techniques and food pairing secrets. The farm’s location on a biodynamic, organic estate adds a layer of authenticity and sustainability often appreciated by discerning travelers.

Scenic Drive: Chianti Hills and the Road to San Gimignano

Post-lunch, your route takes you along the famed Chianti wine road. The rolling, vine-covered hills are a quintessential image of Tuscany. As your driver navigates through cypress-lined roads, you can enjoy the views and discuss the region’s famous wines. The drive itself is an experience—unhurried, scenic, and filled with photo opportunities.

Final Stop: San Gimignano – The Towered Town

Your last destination is San Gimignano, often called the “Medieval Manhattan” due to its skyline of historic towers. Once boasting more than 70 towers, now around 14 remain, giving the town a distinctive profile. The self-guided visit is perfect for wandering through cobblestone streets, exploring the main square, and admiring the medieval architecture.

The town is celebrated for its Vernaccia di San Gimignano, a crisp white wine that pairs beautifully with local saffron and the town’s famed white truffles. Don’t forget to indulge in the reputedly “best ice cream in the world”—a claim many visitors happily agree with, and one reviewer specifically mentions the town’s culinary delights.

Concluding the Day

You’ll spend about an hour here, soaking in the atmosphere, browsing artisan shops, and perhaps tasting some regional saffron or ham. Afterward, your driver will return you comfortably to Florence, concluding a day filled with sights, flavors, and history.

What Makes This Tour Stand Out?

This tour strikes a balance between structured sightseeing and genuine local experiences. The private transportation makes it flexible and relaxing, especially compared to crowded group tours. The lunch and wine tasting are thoughtfully curated, emphasizing regional flavors, local producers, and authentic farm-to-table offerings.

Guests have praised guides and drivers for their knowledge and friendliness—Debra’s review highlights how “Daniel was a great driver,” which can make a significant difference in your overall enjoyment. The opportunity to visit a biodynamic farm and taste multiple wines, oils, and balsamics adds value that many tours don’t include.

A potential consideration is that, since this is a self-guided exploration at each stop, it requires some initiative and comfort with wandering independently. If you’re someone who appreciates guided tours with commentary, this might be a more relaxed, self-directed day.

Who Is This Tour Best For?

If you’re looking for a personalized, authentic Tuscan experience with a focus on food, wine, and history, this tour fits the bill. It’s perfect for couples, small groups, or families seeking a leisurely day with plenty of tasting and culture. Travelers who value off-the-beaten-path destinations like Volterra will especially appreciate the more relaxed pace and fewer crowds.

This tour also suits those who enjoy scenic drives and curated food experiences, plus are comfortable exploring on their own at each stop. It’s a great option if you want to combine sightseeing with culinary delights in a way that feels intimate and genuine.

Frequently Asked Questions

What is included in the price?
The tour includes private transportation, all tastings (wine, olive oils, balsamic vinegar, truffle oil), a delicious Tuscan lunch, bottled water, and visits to the selected sites.

Is this tour suitable for children?
While the tour is mainly cultural and culinary, children who enjoy local food and scenic drives will find it enjoyable. However, specific ages aren’t mentioned, so it’s best to consider your family’s preferences.

How long is the drive from Florence to each stop?
The drive from Florence to Volterra is about 1.5 hours, and from there to San Gimignano via the Chianti hills is a scenic journey, likely another 30-45 minutes.

Can I customize the itinerary?
Since this is a private tour, you can discuss your interests with the driver beforehand. However, the structured stops are predefined.

What should I wear?
Comfortable shoes for walking, especially on cobblestone streets, and layers for varying weather are recommended.

Is lunch included, and what type of food can I expect?
Yes, lunch is included. You’ll enjoy authentic Italian dishes like bruschetta, homemade pasta, cured meats, pecorino cheese, and dessert, paired with regional wines.

Are there any additional costs?
Not unless you decide to purchase extra drinks or souvenirs. The tour covers all tastings and meals described.

How much time is spent at each location?
About 1 hour 30 minutes in Volterra, 2 hours for lunch and farm visit, and 1 hour in San Gimignano.

Are guides available at the sites?
This tour is self-guided at each stop; no guides are included at the sites unless requested in advance at an extra cost.

What is the cancellation policy?
You can cancel free of charge up to 24 hours before the tour, receiving a full refund.

Final thoughts

This private tour offers a well-rounded taste of Tuscany’s historic towns, gastronomic delights, and scenic landscapes. It’s ideal for those who value a flexible, intimate experience with a focus on local food and wine. The combination of cultural exploration, delicious Tuscan cuisine, and lush vistas creates a memorable day, especially if you’re eager to avoid large group tours and seek a more personalized journey.

Whether you’re a history buff, a wine lover, or simply looking to soak in Tuscany’s enchanting scenery, this outing provides an authentic slice of Italy’s heartland. The relaxed pace, high-quality tastings, and charming towns make it a worthwhile addition to any Florence itinerary.