PRIVATE EXCURSION: Volterra & San Gimignano + wine tastings (from Livorno Port)

Exploring Tuscany’s iconic towns and rolling hills on a private excursion from Livorno offers an authentic taste of Italy’s countryside and history. This tour combines visits to Volterra and San Gimignano, two of the most photogenic medieval towns, with a scenic drive along the famed Chianti wine road and a leisurely tasting of some of Italy’s best wines. It’s a well-balanced trip that focuses on personalized experiences, making it ideal for those who prefer a tailored approach rather than large-group tours.

What I really appreciate about this experience are two key elements. First, the expert guides—the reviews consistently praise guides like Andrea and Laura for their friendliness and extensive knowledge, which makes the day both informative and lively. Second, the wine and food pairing at the biodynamic farm is a standout—expect a substantial, delicious Tuscan lunch paired with five different Chianti wines, which is excellent value compared to typical wine tastings.

A potential consideration is the timing—while the itinerary is well-planned, the self-guided visits at Volterra and San Gimignano mean you’ll need to manage your own exploration, which can be a plus or a minus depending on your preference for guided tours.

Key points / Takeaways

Personalized private experience: The private nature ensures a tailored, relaxed day away from large crowds.
Expert local guides: Their friendliness and knowledge elevate the trip, making it more than just a sightseeing drive.
Stunning views and historic towns: Expect breathtaking vistas of the Tuscan hills and well-preserved medieval architecture.
High-quality food and wine: The farm lunch and tastings deliver authentic flavors and excellent value.
Flexible free time: After guided parts, you get some time to explore independently at each stop.
Cost and value: At around $312 per person, the experience offers good value considering the private transport, guided insights, and meal.

Starting Point and Transportation: Comfort and Convenience

This tour begins early, with pickup at the Livorno cruise terminal at 8:00 am, a sensible time that maximizes your day. You travel in an air-conditioned vehicle, which makes the approximately 8-hour adventure comfortable, especially on hot days. The private transportation means you won’t be squeezed into a large bus with strangers—perfect if you prefer a more intimate and flexible experience.

A notable benefit from reviews, such as Jennifer’s, is the professionalism of the driver and guide, who don’t just shuttle you around but also provide insightful commentary along the way. This personal touch helps you feel connected to the landscape and history of Tuscany, even during the drive.

First Stop: The Enchanting Town of Volterra

Your first destination is Volterra, a town perched atop a hill that offers sweeping views of the Tuscan countryside. This spot is a favorite among travelers for its blend of Etruscan relics, Roman ruins, and medieval charm. With about 1.5 hours set aside for a self-guided visit, you’ll have time to wander its narrow streets and admire its Roman Amphitheater, Medici Fortress, and the main square with the Cathedral and octagonal Baptistery.

One of the standout features here is the ancient city gates—some still standing from the Etruscan period—reminding you of the town’s long history. While admission is free, I recommend bringing comfortable shoes because walking around the cobblestones can be a workout.

Jennifer, one of the reviewers, highlights how her guide provided excellent information on the area’s history and wine, adding depth to her visit. This suggests that even during your free time, if guided assistance is available, it can enrich your experience.

Scenic Drive: The Chianti Hills

After exploring Volterra, your journey continues along the famous Chianti wine road—a highlight in itself. The drive through gentle hills dotted with olive groves, cypress trees, and vineyards is a visual feast. The scenery is quintessential Tuscany, offering plenty of perfect photo opportunities.

Traveling with a knowledgeable guide like Andrea, mentioned favorably by Savanna G, means you’ll gain insights into the landscape, the history of wine production, and the area’s agricultural significance. The drive also provides a moment to relax and soak in the serenity of these iconic hills.

The Farm Experience: A Tuscan Feast and Five Wines

The next stop is the Podere La Marronaia- Le Colonne Biodynamic Winery & Farm, situated at a panoramic vantage point. This farm is more than just a tasting room; it’s a window into Italy’s sustainable and biodynamic wine culture.

Here, you’ll enjoy a three-course Tuscan lunch—a generous spread of bruschettas, homemade pasta, cold cuts, Pecorino cheese, and more. As one reviewer, Savanna G, notes, the lunch was “fantastic” with “great pairings,” and the wine tastings included Chianti, Sangiovese, Vernaccia, and even Super Tuscans. The farm also offers tastings of olive oil, balsamic vinegar, and truffle oil, giving you a well-rounded flavor experience.

This part of the tour is often cited as the highlight for its combination of delicious food, outstanding wines, and scenic setting. At around two hours, it’s a leisurely segment that balances tasting with learning about wine production and local food traditions.

San Gimignano: Medieval Marvel and Gelato

After lunch, your adventure continues to San Gimignano, a UNESCO World Heritage site famous for its medieval towers. With about an hour of free time, you’ll be able to stroll its narrow streets, admire the skyline of more than 70 towers that once defined its skyline, and soak in the atmosphere of this “Town of Fine Towers.”

Don’t miss tasting the famous gelato at Gelateria Dondoli—many travelers swear it’s the best in Italy. The town is also renowned for its white wine, Vernaccia di San Gimignano, which pairs nicely with the local saffron and other delicacies. The town’s compact size makes it easy to explore at your own pace, which many reviewers appreciate—especially Laura, who was praised for her knowledge and friendly manner.

Practicalities and Overall Value

This tour’s cost of about $312 per person includes private transport, the guided drive, wine tastings, lunch, bottled water, and entrance fees (where applicable). Considering the personalized nature, the quality of food and wine, and the expert guidance, it seems a solid value—especially for those who prefer a more intimate experience over the hustle of larger groups.

Reviews emphasize the professionalism and friendliness of guides like Andrea and Laura, who make the day both educational and enjoyable. The flexibility of free time at each stop allows for spontaneous exploration or relaxing breaks, which is ideal for travelers who want to soak up the atmosphere at their own pace.

Who Will Love This Tour?

If you’re a traveler who appreciates authentic food and wine experiences, this tour offers a meaningful taste of Tuscany’s culinary and cultural richness. It’s especially suitable if you value personalized service and comfort, rather than large-group bus tours. History buffs will enjoy the Etruscan and medieval sights, while wine lovers will find the tastings and vineyard visit particularly rewarding.

However, if you prefer guided tours with detailed explanations at each site, you might find the self-guided portions a bit light. Also, be mindful of the time constraints—if you want to spend more time in each town, you may need to extend your stay or look for a different itinerary.

This private excursion from Livorno offers a well-rounded day that balances history, scenery, cuisine, and wine in Tuscany. With expert guides, scenic drives, and a delicious farm lunch, it provides a genuine experience without feeling rushed. The flexibility of free time at each stop means you can tailor your exploration, whether that involves snapping photos, tasting local products, or simply soaking in the views.

It’s perfect for travelers who want a curated, stress-free day with authentic touches, especially if they’re arriving via cruise and want to see the highlights comfortably. The strong reviews highlight the value and quality, making it a worthwhile choice for those eager to experience Tuscany’s magic in one day.

Is this tour suitable for people who don’t want guided walks?
Yes, the visits at Volterra and San Gimignano are self-guided, so you can explore at your own pace once you arrive.

What’s included in the price?
You get private transportation, an expert driver, bottled water, a three-course Tuscan lunch, and wine tastings at the farm—five different Chianti wines plus others.

Can I cancel this tour?
Yes, you can cancel for free up to 24 hours in advance, making it flexible if your plans change.

How long does each stop last?
You’ll have approximately 1.5 hours in Volterra, 2 hours at the farm for lunch and tastings, and 1 hour in San Gimignano for sightseeing.

Is this tour good for wine lovers?
Absolutely. The farm offers five wine tastings, including Chianti and Super Tuscan, and the guides are praised for their wine knowledge.

What’s the best time of year for this tour?
While the tour runs year-round, the scenery and outdoor activities are most enjoyable in spring and fall when the weather is mild.

Do I need to book in advance?
Yes, booking about 66 days ahead is common, and the tour typically fills quickly given its popularity.

This private day trip from Livorno balances discovery and relaxation, making it a perfect way to taste Tuscany’s essence without the crowds. Whether you’re a history enthusiast, a wine lover, or simply after a relaxing scenic day, this tour can deliver a memorable experience.