PRIVATE EXCURSION: Visit Siena & Chianti with lunch and tastings

A Taste of Tuscany: Siena & Chianti Private Excursion

Imagine stepping into a postcard—rolling vineyard-covered hills, ancient city walls, and medieval towers. For around nine hours, this private tour from Livorno offers a chance to experience the essence of Tuscany through visits to Siena, the Chianti wine region, and San Gimignano. The cost is $347.58 per person, which, considering the personalized attention, expert driver, and inclusive tastings and lunch, offers good value for those eager to savor authentic flavors and stunning scenery in one day.

What we love most about this experience is the intimate pace—you’ll have plenty of time to explore Siena at your own speed and enjoy an authentic Tuscan farm lunch paired with exceptional wines. Plus, the chance to walk through San Gimignano’s ancient streets and see its famous towers adds a dash of history and charm. The only consideration is that, being a private tour, it’s tailored for those seeking a personalized, relaxed day rather than a high-energy, group-heavy excursion. It’s ideal for travelers craving an authentic, scenic, and wine-rich immersion into Tuscany, especially if you appreciate good food, picturesque towns, and the quiet beauty of Italy’s countryside.

Key Points

• Personalized Experience: Private tour tailored to your schedule and interests.
• Authentic Tasting & Lunch: Includes 5 wine tastings and a traditional Tuscan 3-course meal.
• Flexible Exploration: Free time in Siena and San Gimignano allows for spontaneous discovery.
• Stunning Scenery: Travel along the Chianti wine roads with breathtaking views.
• Expert Guidance: Driver provides helpful tips, enriching your visit without a formal guide.
• Optimal Timing: Itinerary designed to fit cruise schedules, with return to Livorno by 5:30 PM.

Exploring Tuscany: A Journey Through Beauty and Flavor

When we think of Tuscany, images of endless vineyards, medieval towns, and artisanal foods immediately come to mind. This tour offers a well-rounded taste of that lifestyle, combining scenic drives, historic sights, and culinary delights. It’s designed for those who want to avoid the cookie-cutter bus tours and instead experience Italy at a more relaxed, intimate level.

The Drive Through Chianti’s Rolling Hills

We loved the way the journey begins—being picked up directly from the cruise port, whisked away in an air-conditioned vehicle with a knowledgeable driver. The drive through Chianti’s famous wine roads is itself a highlight. Think gently rolling hills, dotted with olive groves and cypress trees, and the kind of scenery that makes you want to grab a camera every few minutes. If you’re a fan of picturesque landscapes, this part of the trip is sure to satisfy.

Your driver will share tidbits about the region’s history and agriculture, making the scenic drive as educational as it is beautiful. It’s a peaceful start that sets the scene for a day of indulgence.

Siena: Medieval Charm and Vibrant Life

Your first stop, Siena, is a true jewel of Tuscany. With about 1 hour and 30 minutes to explore, you can wander the UNESCO-listed historic center at your own pace. The Piazza del Campo, with its shell shape and lively atmosphere, is arguably one of Italy’s most beautiful squares. Here, you might want to sit on a bench, soak in the views, and imagine the scenes of the famous Palio horse race that takes place twice a year.

The guide (or driver, in this case) will give you some handy tips on navigating Siena, helping you find local spots or hidden corners. Expect to see decorative architecture and church facades that scream medieval Italy. The charm of Siena lies not just in its sights but in its palpable sense of time standing still.

A reviewer noted, “Siena was beautiful, but the best part of the excursion was the winery luncheon,” capturing how the town’s beauty complements the core experience of food and wine.

The Farm Lunch and Chianti Tasting

The highlight for many travelers is the stop at Podere La Marronaia-Le Colonne, a biodynamic winery and farm on a hilltop with panoramic views. Here, you’ll enjoy a 3-course Tuscan lunch featuring home-made pasta, local cold cuts, Pecorino cheese, and fresh bruschettas. The food alone is worth the trip, but it’s the pairing with five different wines—including Chianti, Chianti Riserva, Sangiovese, Vernaccia, and Super Tuscan—that elevates the experience.

Many reviews rave about the authenticity of this farm experience. One traveler, Dawn, said, “Guide was on time and very informative,” and emphasized the wine luncheon as a highlight. The chance to taste wines directly from the producers, paired with local delicacies, is a rarity that offers good value and genuine insight into Tuscan cuisine.

The Enchanting Streets of San Gimignano

In the early afternoon, you’ll visit San Gimignano, a town famed for its medieval towers—originally over 70, now just 14 remain—earning it the nickname, “Town of Fine Towers.” The self-guided visit of about an hour gives you time to stroll through ancient streets, admire artisans’ crafts, and perhaps sample the famous Vernaccia di San Gimignano, a crisp white wine made from local grapes.

While walking, you’ll notice the Saffron and Golden Ham specialties—extra treats for those interested in local flavors. And, of course, don’t miss a scoop of Gelateria Dondoli—some say it’s the best gelato in the world.

Returning to Livorno

The tour wraps up with a relaxing drive back to Livorno by 5:30 PM, giving you time to freshen up before heading to your next adventure or dinner. The well-planned timing ensures a full day without feeling rushed.

The Practical Side: What Travelers Need to Know

This tour includes private transportation, air-conditioned vehicle, and local driver who doubles as a wealth of regional knowledge. The five wine tastings and a three-course Tuscan lunch make the experience both indulgent and educational, especially for those curious about regional wines and traditional dishes.

The cost of $347.58 per person might seem high, but considering the private nature, personalized attention, and inclusions, it offers considerable value—particularly if you enjoy wine and authentic cuisine. It’s worth noting that the tour is non-refundable and cannot be rescheduled, so plan accordingly.

The tour is designed for most travelers, with minimal physical demands. If you’re interested in adding a guide, it’s possible, but with a one-week notice and extra fee. The itinerary is flexible enough to suit cruise schedules, making it a smart choice for shore excursions.

Who Should Consider This Tour?

This private Tuscany exploration suits culinary enthusiasts, history lovers, and scenery seekers who appreciate the quiet beauty of the Italian countryside. It’s ideal for couples, small groups, or solo travelers wanting an intimate experience without the rush of larger tours. If you love authentic local food, wines, and medieval towns, this trip offers a well-rounded taste of Tuscany’s highlights.

Travelers who value relaxed pacing and customized experiences will find this tour particularly appealing. It’s also perfect for those who want a scenic drive with stops that allow both sightseeing and genuine culture.

FAQs

How long is the tour?
The entire experience lasts about 9 hours, from pickup in Livorno to return, including stops in Siena, the Chianti farm, and San Gimignano.

Is this a group or private tour?
This is a private tour, so only your group will participate, offering a more personalized and relaxed experience.

What’s included in the price?
You get private transportation, five wine tastings, bottled water, a three-course Tuscan lunch, and an expert driver. A guide is available upon request for an additional fee.

Can I customize the itinerary?
The itinerary is designed to fit your cruise schedule and allows some flexibility, but any specific customizations need to be arranged in advance.

Are there any physical requirements?
The tour involves walking through towns and some uneven streets but is generally suitable for most travelers who can handle light walking.

What wines will I taste?
Expect to sample Vernaccia, Super Tuscan, Sangiovese, Chianti, and Chianti Reserve wines.

Is lunch included?
Yes, a traditional Tuscan meal with local ingredients is included, along with wine tastings.

What if I want a guide to join me?
A guide can be arranged with a week’s notice, but it incurs an additional cost.

In The Sum Up

This private tour from Livorno offers an excellent way to experience Tuscany’s beautiful landscapes, historic towns, and delicious wines at a relaxed pace. The combination of personalized service, authentic local food, and stunning scenery makes it a memorable choice for those eager to get a genuine taste of Italy. Whether you’re a wine lover, a history buff, or simply want to enjoy Tuscany’s peaceful charm, this trip delivers on many fronts.

While it’s a bit of a splurge, the inclusions—especially the private transportation, lunch, and wine tastings—offer a rich experience that justifies the price. It’s perfect for travelers who value authenticity and comfort over large group excursions, and who want to take home more than just photos—memories of a true Tuscan day.

Ready for an immersive, scenic, and flavorful day in Tuscany? This private Siena and Chianti tour from Livorno might just be exactly what you’re looking for.