A perfect wine day has a spine. This one runs from vineyard rows to cellar tastings with a real sommelier guiding the whole rhythm. You’re in Bolgheri, and you’ll hear how the area’s traditions and vine character shape what ends up in your glass.

I especially like the host, Simone Vergamini. His credentials are the kind you can feel in the details, and the format leaves space for questions. I also love that you’re not doing a quick drive-by: you visit two representative wineries with time for vineyards, cellars, and then the tasting itself.

One consideration: the day is long (8 to 9 hours) and lunch in Bolgheri is not included in the tour price. You’ll want to budget extra time and a little extra money, and make peace with the fact that you’re getting two focused stops rather than a “see everything” tour.

Key highlights to know before you go

• Simone Vergamini as your sommelier host, with serious competition experience and plenty of Q&A time
• Two Bolgheri winery visits (usually Chiappini and Grattamacco) with vineyards, cellars, and tastings
• Included snacks and pairing-style bites like extra virgin olive oil, bread, cheese, and salami
• A Bolgheri lunch pause (typical local products) where he’ll book the wine shop Tognoni or use your preferred spot
• Air-conditioned private transportation plus bottled water, so the day stays comfortable
• A full day schedule starting at 9:30 am, meaning you should plan your morning and evening accordingly

Meet Simone Vergamini, your sommelier for the day

This tour is built around one strong idea: tasting is easier when someone can explain what you’re tasting. Your guide is Simone Vergamini, who’s been recognized as Best Sommelier of Tuscany in 2023 and has placed in the Best Sommelier of Italy competition in multiple years (2018, 2021, and 2022). That matters because he isn’t just pouring—he’s guiding you through the logic behind the wines.

Simone’s style also fits the way wine trips should work. During the drive and between stops, he talks through the area’s history and traditions, then connects that story to the vines and the local peculiarities. If you like asking why one wine tastes one way and another tastes different, this format gives you room for it instead of rushing you out the door.

You’ll also notice the pacing: he uses the journey time, not just the tasting time. That means you’re not only collecting impressions—you’re collecting context, which makes the tastings more meaningful.

Getting from Lucca to Bolgheri without losing the day

The tour starts at 9:30 am and runs about 8 to 9 hours total. It includes an air-conditioned vehicle and bottled water, which is a simple comfort detail that makes a long day feel manageable.

Pickup is offered, so you’re not left trying to coordinate your own transfer. For me, that’s a real quality-of-life upgrade on wine tours, because the day is already structured around timing at the wineries. One less logistical headache means you arrive more relaxed and ready to taste.

Also, the tour is private. That’s important because you can move as a group, ask more direct questions, and keep the pace that fits your group. If you’re traveling with friends, this is a great “everyone gets attention” setup rather than a crowded group where you can’t hear the explanation.

Stop at Chiappini: the first vineyard walk and cellar tasting

The first winery stop is Chiappini, and you get about 1 hour 30 minutes there. The structure is straightforward and effective: you’ll visit the vineyards, tour the cellar, and taste the wines the winery produces.

What I like about starting here is the way it sets the day’s baseline. You begin with the vine setting—seeing the vineyard side of the story—then you move into the cellar where the winemaking decisions become visible through the process. After that, tasting feels less random, because you already understand what the place contributes before you judge the wine in the glass.

The ticket for admission is included, so you’re not juggling extra payments mid-day. You’ll also get tasting-related snacks: the tour includes bites like extra virgin olive oil, bread, cheese, and salami. That combination is practical for wine touring, because it gives you something solid and local to reset your palate.

A small drawback to keep in mind: it’s only one hour and a half. That sounds quick, but it’s actually a good format if your goal is focus. If you want a super slow, open-ended stroll through every corner of a cellar, you may wish you had more time at each winery. But for most people, the pacing keeps the day from dragging.

Tenuta Podere Grattamacco: second stop, more Bolgheri character

Your second winery visit is usually Tenuta Podere Grattamacco, also timed at about 1 hour 30 minutes. Like the first stop, you’ll move through vineyards, visit the cellar, and taste the wines produced there. Admission ticket is also included for this stop.

This is where the day becomes a comparison lesson, not just a series of separate tastings. Because you’re visiting two wineries that are representative of the Bolgheri area, you’ll naturally start noticing how local conditions and different approaches translate into different wine expressions.

Simone’s background helps here. When you’re comparing, it’s easy to get lost in personal preference alone. He can steer you toward what to pay attention to—how the area’s peculiarities show up, and how that differs from one winery’s choices to the next. If you like understanding rather than just sampling, this part tends to be a highlight.

One practical note: the day is structured so you’re not overspending your energy too early. By the time you reach the second winery, you’ve already had snacks and an initial tasting to ground your palate, and you’re moving forward with momentum.

Also worth knowing: if Chiappini and Grattamacco aren’t the exact picks on your date, the tour description indicates alternatives such as Tenuta di Vaira and Le Novelire. The key idea stays the same—two winery visits in Bolgheri with vineyards, cellars, and tastings.

Bolgheri lunch at the village’s wine-shop stop

Between visits, you’ll stop in Bolgheri for lunch based on typical local products. This is about 2 hours, and it’s a relaxed moment in the middle of the day.

Lunch is not included in the tour price, but Simone arranges it. The plan is either your favorite restaurant or he’ll book Tognoni wine shop for you. For me, that’s a smart middle ground: you get local sourcing through the wine-shop option, and you’re not left trying to guess where to eat in a small village during a full day.

What you should do before you arrive: decide what kind of lunch fits your day. If you want a classic sit-down meal with local flavor, ask for that. If your group has dietary needs, you’ll want to communicate them when Simone books the lunch so the plan doesn’t become a scramble later.

Because you’ve had tastings already, lunch is also your practical reset. Expect the meal to pair well with what you’ve been tasting, and use the time to pace your drinking so the afternoon stays enjoyable.

What’s included in the tasting day (and what isn’t)

The tour includes several things that make it feel complete as a package. You get an air-conditioned vehicle, bottled water, and the wines (alcoholic beverages) as part of the experience. There are also snacks like extra virgin olive oil, bread, cheese, and salami.

You also get the admission tickets for the two winery stops. That’s not just convenience—it’s part of the value. Wine tastings can turn into an add-on festival if you start from scratch, so having the winery admissions covered keeps the day straightforward.

What is not included is lunch in Bolgheri. Simone can book it, but you’ll pay it separately. If you’re budgeting, treat lunch as an expected extra cost rather than a surprise.

Optional tipping is also mentioned as a possibility. That’s common with private guides. If you’ve had a strong day and you want the gesture to match the service quality, it’s reasonable.

Duration, pace, and how to plan your day

With a 9:30 am start and roughly 8 to 9 hours total, this is a full-day wine outing. The schedule keeps you moving, which is usually what you want on a first visit to a wine region: you taste, you learn, and you still have time to enjoy the village stop.

Because there are two winery stops and a lunch pause, you’ll want to go into the day ready for a steady flow:

• comfortable shoes for vineyard touring
• a light plan for the evening after (you’ll likely feel it, even with breaks)
• curiosity with questions lined up in your head

The tour also requires good weather. If conditions are poor, it can be canceled and you’ll be offered a different date or a full refund. That’s a normal reality in outdoor vineyard settings, and it’s smart that the plan doesn’t pretend weather won’t matter.

Price and value: is $347.05 per person fair?

Let’s talk about the number plainly: $347.05 per person. For a private day in Tuscany, that’s not a budget price. But it also isn’t just a car rental and a promise.

You’re paying for:

• a private, sommelier-led experience with a guide holding major competition credentials
• two wineries with vineyard and cellar time, plus tasting
• winery admission included at both stops
• snacks and bottled water, and wine/other alcoholic beverages as part of the tasting day
• air-conditioned transport and a structured schedule that avoids time-wasting

The lunch cost isn’t included, so you’re responsible for that add-on. But if your alternative is paying separately for transport, winery tickets, and hiring someone to explain what you’re seeing, this often ends up feeling like the efficient choice.

I think the best “value test” is simple: if you care about wine beyond drinking and you like getting guided insight, this price feels easier to justify. If you’re purely looking for low-cost tastings and don’t want explanations, you could find cheaper options. Still, you’d be giving up the specific kind of attention Simone brings to the day.

Who this private Bolgheri tour is best for

This is a great match for people who want a guided wine day rather than a self-guided checklist.

I’d point it toward:

• couples or friends who like asking questions and comparing what they taste
• wine lovers who want to understand how vines and local traditions connect to the wines
• travelers who prefer pickup and a planned schedule over navigating transport and winery timings

It’s also set up well for groups who want privacy. Since it’s a private tour/activity with only your group participating, you get a calmer, less rushed experience than you would in a large multi-group format.

If you’re visiting Tuscany and you keep hearing Bolgheri gets special attention, this tour gives you a structured way to experience that without guessing.

Should you book this private wine tour?

Book it if you want your day in Bolgheri to feel guided, not chaotic. The biggest strength is the combination of a top-tier sommelier host and two focused winery experiences with vineyard and cellar time, plus tasting and local snacks. If Simone’s credentials and the chance to ask questions during the day are appealing, you’ll likely feel you got your money’s worth.

Skip it or consider alternatives if you’re chasing the most stops possible in a single day or if lunch being extra cost would stress your budget. Also, remember the tour depends on good weather, so it’s best if your schedule can flex.

If you want a well-paced, high-attention wine day with a real expert steering the story, this is the kind of booking I’d feel good about.

FAQ

What is the tour duration?

The experience lasts about 8 to 9 hours.

What time does the tour start?

It starts at 9:30 am.

Where does the tour begin and end?

It ends back at the meeting point. The start point is the meeting point provided for the activity.

Are pickup options available?

Yes, pickup is offered.

Which wineries are typically visited?

The tour usually visits Chiappini and Tenuta Podere Grattamacco. Alternatives can include Tenuta di Vaira and Le Novelire.

Is lunch included in the price?

No. Lunch in Bolgheri is not included, though Simone can book it (either your preferred restaurant or Tognoni wine shop).

What’s included with the tastings?

Included items include bottled water, the wines/alcoholic beverages, and snacks such as extra virgin olive oil, bread, cheese, and salami. Admission tickets for the wineries are included.

Do I need good weather for the tour?

Yes, the experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Is cancellation free?

Yes. You can cancel up to 24 hours in advance for a full refund.

You Might Also Enjoy

Traditional Farmhouse Cooking Experience in Lucca with Lunch or DinnerFlorence Duomo Skip-the-Line Timed Entry Ticket & Panoramic ViewsFlorence: Guided Food and Wine Walking TourPrivate tour from Florence to CORTONA & MONTEPULCIANO