Chianti, SuperTuscan & San Gimignano – 2 wineries and light lunch

Imagine spending a day in the heart of Tuscany, exploring the medieval splendor of San Gimignano and tasting some of Italy’s finest wines at two carefully selected wineries. For around $459 per person, this 7-hour private tour offers a relaxed yet immersive way to experience authentic Tuscan hospitality, stunning vineyard vistas, and exceptional wines. Led by knowledgeable guides—such as Massimo and Vito—this experience promises personalized attention, making it perfect for those craving a more intimate connection with Tuscany’s wine country.

What we love most about this tour is how it balances educational wine tastings with the chance to wander through San Gimignano’s historic streets—an ideal mix for lovers of culture and wine. Plus, the hosts at the wineries are praised for their warmth and expertise, making every tasting feel like a visit to a friend’s cellar. The only consideration? The tour charges extra for wine tastings and lunch, so budget accordingly if you want to indulge fully. This experience suits anyone eager to explore Tuscany beyond the usual tourist spots—especially those who appreciate good wine, scenic views, and a personal touch.

This experience made our article of Discover 15 Great Tours In Montecatini Terme.

Key Points

• Personalized experience: Private tour with only your group for a more intimate visit.
• Expert guides: Friendly, knowledgeable guides like Massimo make the difference.
• Stunning scenery: Expect breathtaking vineyard views and picturesque streets.
• Authentic visits: Two local wineries offering personal, welcoming atmospheres.
• Culinary delight: Light lunch and wine tastings highlight regional flavors.
• Flexible for families: Children are welcome; just note they can’t sample wine.

Exploring Tuscany’s Hidden Gems: A Deep Dive into the Chianti, SuperTuscan & San Gimignano Tour

Discovering the Heart of Tuscany—An Itinerary Overview

This private tour begins with a visit to San Gimignano, famously known as the “Medieval Manhattan” for its skyline of well-preserved towers. For about 50 minutes, you’ll stroll through its narrow streets, soaking in the ancient charm, local artisan shops, and vibrant piazzas. The town’s admission is free, so your only costs are for personal souvenirs or optional extras.

After soaking up history and charm in San Gimignano, the journey continues into the countryside, where you’ll visit two local wineries. These are not big commercial operations—they’re small, family-run estates that invite you into their world, sharing stories behind each bottle. Expect to spend ample time touring the cellars, where wine is aged in wooden barrels, gaining that complex flavor you love.

The tour wraps up with a light lunch—a perfect chance to enjoy regional delights alongside your wine tastings. While the lunch is optional and costs around €35 per person, many reviews mention it’s hearty and satisfying, perfectly complementing the wines.

What Makes This Tour Stand Out?

Two standout features make this experience memorable. First, the personalized, private nature of the tour ensures every question gets answered, and you won’t feel lost in a crowd. Second, the guides’ warmth and expertise shine through, with reviewers mentioning guides like Simona and Massimo by name as being attentive, knowledgeable, and engaging.

The scenic views of rolling vineyards, cypress-lined roads, and medieval towers are so striking that many travelers comment on how those vistas alone make the day special.

What’s the Balance Between Cost and Value?

At $459.81 per person, this tour provides a curated, intimate experience that would be difficult to replicate on your own without planning extensively. The inclusions—visit to San Gimignano, two wineries, private transport, and a guided experience—offer strong value, especially considering the personalized service. Additional expenses—for wine tastings and lunch—are extra, but reviews confirm the quality and authenticity of these offerings.

Who Will Love This Tour?

This experience fits travelers who want more than just a quick look at Tuscany. It’s ideal for those who value authenticity, enjoy learning about wine, and prefer traveling in a small, private group. Perfect for couples, friends, or small families, it’s especially praised for the warmth of guides and the stunning scenery. Children are welcome, though they can’t participate in wine tastings, making it suitable for family outings as well.

In-Depth Look at the Itinerary

San Gimignano — The Medieval Jewel

The tour starts with a 50-minute visit to San Gimignano, a UNESCO World Heritage site. It’s famed for its medieval towers, some dating back to the 12th century, which create a distinctive skyline. Wandering through its narrow streets, you’ll find vibrant cafes, artisan shops, and historic sites. It’s an ideal place for photography and soaking in Italy’s past.

Expect to be impressed by how well-preserved the town is and how the medieval architecture interacts with lively modern life. Many reviews highlight the town’s beauty: “The town of San Gimignano was beautiful,” one traveler notes. The free admission means you can spend your time exploring, shopping, or just enjoying the vibe without feeling rushed.

Visiting the Wineries — Personal, Educational, and Delicious

The essence of this tour lies in its visits to two local wineries. These aren’t factories—they’re small, family-run wineries that open their doors, cellars, and hearts. You’ll see where the wine is stored in wooden barrels, and guides will explain the aging process, giving you a behind-the-scenes look that big commercial wineries often skip.

The reviews speak volumes: “The wineries were so personal, we felt like we were visiting old friends,” says one traveler. Guides such as Jessica and her family are praised for their welcoming attitude and their ability to communicate their passion for wine.

Expect to taste Chianti, SuperTuscan, and other regional wines, often paired with local snacks or light tapas. These tastings are included in the tour price, but additional wine tastings in both wineries are an extra €75 per person. Many travelers find that the wines are of high quality, memorable, and complement the scenic surroundings perfectly.

The Light Lunch — Satisfying and Authentic

While optional, the light lunch is often highlighted as a highlight. Priced at about €35 per person, it typically includes regional specialties, hearty enough to sustain you through the afternoon. Jessica’s family, according to reviews, makes a remarkable meal that pairs beautifully with the wines. This is a chance to sit down, relax, and savor the flavors of Tuscany.

Practical Details That Make or Break the Experience

Transportation

The tour includes pickup and drop-off, which means you avoid a lot of hassle navigating public transportation or renting a car. The guide/driver—like Vito—receives praise for his friendly, professional manner and safe driving, ensuring a smooth day.

Group Size and Flexibility

Being a private tour, only your group participates. This means more flexibility, personal attention, and the chance to ask endless questions. Travelers report feeling like they got a personal tour experience rather than being part of a crowd.

Duration and Timing

Spanning approximately 7 hours, the schedule balances sightseeing, tasting, and relaxing. The timing is arranged to maximize your experience without feeling rushed or overly long.

Cost Breakdown and Extra Expenses

While the base price is $459.81, additional costs include wine tasting (€75) and lunch (€35). Reviewers say these extras are worthwhile, especially given the quality of the food and wine. Since the tour is booked on average 75 days in advance, planning ahead ensures you secure your preferred date and avoid last-minute disappointment.

Why This Tour Is a Win for Authentic Tuscany Fans

If you’re looking for something beyond the typical tourist trails, this tour offers genuine local interactions, stunning scenery, and high-quality wine experiences. Its focus on small, family-run wineries ensures you get a taste of real Tuscan hospitality. The guided insights, combined with free time in San Gimignano, strike a perfect balance between structure and freedom.

The reviews highlight the presence of knowledgeable guides, like Massimo and Simona, who make the experience engaging and personal. Many travelers mention how they felt like they were visiting old friends, which speaks to the warm, welcoming atmosphere.

Frequently Asked Questions

Is this a group or private tour?
It’s a private tour, meaning only your group participates, providing a more personal experience.

How long is the tour?
The tour lasts about 7 hours, including visits, tastings, and lunch.

Are children allowed?
Yes, children are welcome and must be accompanied by an adult. However, those under 18 can’t taste wine.

What’s included in the tour?
Your guide, pickup and drop-off, visits to two wineries, and San Gimignano are included. Wine tastings and lunch are additional costs.

How much do extra wine tastings cost?
They are about €75 per person for tasting at both wineries.

Can I cancel this tour?
Yes, cancellations are free up to 24 hours in advance.

Is the lunch included?
The light lunch is an optional addition, costing about €35 per person.

What are the highlights of San Gimignano?
The medieval towers, historic streets, and vibrant piazzas make it a must-see.

Is transportation provided?
Yes, pickup and drop-off are included in the package.

Who would enjoy this tour most?
Travelers who appreciate authentic wineries, scenic views, and a personalized experience will maximize their enjoyment.

To sum it up, this tour offers a well-rounded taste of Tuscany’s wine, history, and landscapes in a relaxed, private setting. Its blend of guided education, scenic charm, and authentic hospitality makes it ideal for those eager to experience Tuscany beyond the ticketed attractions. Whether you’re a wine enthusiast or simply looking to explore Italy’s countryside in comfort and style, this experience promises memorable moments at an excellent value for those seeking something more personal and genuine.