This is a fast-track way to get out of Florence and into Tuscan wine country. What makes it work is the small-group size and the fact you’re tasting at two wineries, not just sitting through a talk.

I especially like the hands-on feel: you get guided tastings, time with the winemakers, and enough context to start noticing what you like. The day also has a real practical backbone, like comfortable air-conditioned transport and a guide who keeps things moving.

One thing to plan for: lunch isn’t included, so you’ll want to time snacks around the winery stops or budget for food on your own.

Key Things to Know Before You Go

• Max 8 people keeps the vibe personal and makes Q&A actually possible.
• Two winery tastings means you can compare styles and hospitality back-to-back.
• AC minivan transfers help a lot on a 6-hour day, especially in warm months.
• Alcohol is included with the tastings, but the tour still ends back at the meeting point.
• Minimum age 18 applies for wine tasting, so plan accordingly if you’re traveling with younger people.

A Florence Morning That Gets You Into Chianti Fast

This tour is built for people who want results, not just sightseeing time. It starts at 10:00 am, and the whole plan runs about 6 hours, with the day ending back at the same meeting point near Lungarno Amerigo Vespucci.

The biggest practical win is the small group. With a max of 8 people, you’re not fighting for attention. You can ask questions without your guide turning into a racehorse chasing the schedule.

Also, the transport is handled for you. You’ll ride in an air-conditioned minivan, which turns “Tuscany day trip” from a logistics headache into a straight-line plan. If you’ve done wine tours that feel like you’re just being herded, this setup feels more human.

Where the Day Actually Happens: Strada Statale 222 Chiantigiana

The tour heads out through the Chianti area via Strada Statale 222 Chiantigiana. This is one of those routes where you feel like you’re moving through real working countryside instead of a theme park.

At the start, you’ll get time to take in the area and taste real Chianti wine. The value here is that tasting early helps you calibrate your palate. Then, when you get to the wineries, you’re not starting from zero—you already have a baseline.

One small consideration: since this is a working-drive day, you’ll likely spend more time in the van than you would on a purely walking-focused tour. If you prefer long scenic stops over tight timing, keep that in mind.

Winery Stop One: Poggio Al Sole and the Larger-Winery View

Your first winery visit is Poggio Al Sole, and it’s described as a bigger operation compared to the second stop. That matters because a larger winery often has more structured tastings and clearer production steps you can observe.

This is also where you may get a more behind-the-scenes look. In the experiences I drew from, the group even had a chance to see the owner and get a glimpse into the process of making the wine. That kind of access is the difference between tasting and learning.

Expect to taste multiple wines here. If you like comparing styles—same region, different character—this stop is a good fit. And one extra detail stood out in the most memorable versions of the day: basil pasta prepared by Jessica’s mother-in-law. It’s the sort of simple, local touch that sticks in your head because it feels homemade and not staged for tourists.

A drawback to consider: bigger wineries can mean a less “tiny family room” feeling than a small estate. If you’re chasing intimate, quiet charm above all else, the second winery is where you’ll probably feel more of that.

Winery Stop Two: Alterio’s Family-Run Hospitality

Then you head to Alterio, a small family-run winery. This stop is all about contrast, and that’s why the two-winery format works so well. You get a broad look at one end of the spectrum, then a warmer, more personal welcome at the other.

The hospitality is a big part of the appeal here. The team is described as personable, and the wines are a clear highlight. This is also where food pairing shows up in a practical way: they prepare a meal to go with the wine.

That matters on a day like this because lunch isn’t included on paper. A meal-to-go isn’t a substitute for a sit-down lunch, but it does help you avoid the “stumble out of the winery hungry and cranky” problem. If you’re the type who plans around meals, this pairing makes the timing feel more balanced.

If you care about learning how a small producer works—how decisions get made and how hospitality is personal—this second stop is the one to pay attention to. I like that the experience doesn’t just change the wines; it changes the tone of the day.

The Guides Make or Break the Day: Massimo and Simone

With wine tours, the guide’s role is bigger than most people think. They’re not only driving and translating. They set the pace, steer you toward what matters, and explain what you’re actually tasting.

Two guide names came up again and again: Massimo and Simone. In the best versions of the experience, they come across as proud of their region and good at answering questions without rushing you. That combination is rare. You want someone who’s friendly, but also clear enough to help you connect the taste to the place.

On the road, guides also share context about the area and agriculture—how vineyards and winery choices connect to the final bottle. This is the part that turns your tasting from random sips into a pattern you can recognize later.

If you’re someone who asks a lot of questions, the max 8 group size helps. In larger tours, your best questions get swallowed by noise. Here, you’re more likely to get real answers.

What You’re Getting: Tastings, Beverages, and What’s Not Included

Here’s the practical list, and then the meaning behind it.

Included:

• Wine tasting in 2 wineries
• Alcoholic beverages during the tastings
• Transport by air-conditioned minivan
• Driver/guide
• Admission ticket included (for the day’s winery/area access)
• Small group up to 8 people

Not included:

• Lunch

Why this matters: alcohol being included means you can focus on the wine and pairings instead of calculating your budget at every stop. But since lunch isn’t included, you’ll still want a plan for food.

My advice: eat something before the tour starts, then use the meal-to-go moment at the second winery as your anchor. If your first winery has a food pairing, great. If not, you’ll still want a snack in your day bag so the afternoon doesn’t feel like a long gap between tastings.

Also note: the tasting side is set for adults. There’s a minimum age of 18 years in order to taste wine. If you’re traveling with anyone under that age, they’ll need to be accompanied by an adult, and they won’t be part of the wine tasting itself.

Comfort, Timing, and Logistics That Actually Help

This tour ends back at the meeting point, which is reassuring if you’re staying near central Florence. You don’t have to worry about lining up a second bus or taxi after the wine.

The schedule is also straightforward: start at 10:00 am, finish around 6 hours later. That makes it easier to fit into a day you also want to use for museums or dinner plans.

You’ll also get a mobile ticket, which is one less paper thing to manage. And because the start point is near public transportation, it’s convenient if you need to meet the van from a different part of the city.

One consideration: you’ll be in a car for parts of the day, so if you’re prone to motion discomfort, pack what you need. The AC helps, but the route through countryside roads still means you’ll be moving.

Price and Value: What $377.53 Buys You

The price is $377.53 per person for an approximately 6-hour, two-winery tour. On its face, that’s not a “cheap by the glass” situation. But when you break it down, it’s closer to paying for convenience plus access.

You’re paying for:

• Round-trip guided transport from Florence
• Wine tastings at 2 wineries
• Alcoholic beverages included
• A small group capped at 8
• Admission ticket included
• A guide who stays with you the whole time

That’s the value equation. If you tried to copy this yourself, you’d spend time coordinating rides, paying for tastings, and trying to secure winery visits that fit your schedule. Here, the day is structured so you spend your time tasting and learning rather than troubleshooting.

Where it may not feel like great value: if your only goal is a single winery tasting and you don’t care about guided context, you might prefer a shorter, cheaper option. But if you want a real day in Chianti with two distinct stops, this price can make sense.

Who Should Book This Chianti Day Trip

This tour fits best if you:

• Want a small-group day trip rather than a crowd experience
• Like comparing wineries and not just doing one tasting
• Enjoy learning how Tuscany agriculture and production connect to what ends up in your glass
• Appreciate guided conversation with a driver/guide like Massimo or Simone
• Want the comfort of AC transport for a full half-day

It’s also a good match for couples and small friend groups who want a shared plan but don’t want to be stuck in a big bus.

If you’re a hardcore Supertuscan specialist looking for a very specific list of bottles, you might want to ask questions when booking. The tour is branded as Chianti and Supertuscan, but the provided details focus most clearly on tasting in the Chianti area plus two winery visits.

Should You Book This Chianti & Supertuscan Tour?

I think you should book it if you want a smooth, guided wine day that’s actually built around tastings at two wineries and doesn’t eat your whole day in logistics. The combination of a max 8 group, AC van, and guided context from guides like Massimo or Simone is a strong signal you’ll come away with more than just a few sips.

I’d hesitate only if you strongly dislike wine tours that involve driving between stops, or if you absolutely want a full lunch included as part of the package. In that case, you’ll need to plan your food timing carefully—or choose a different tour format.

If your goal is a memorable Chianti day with distinct winery personalities—one larger production experience at Poggio Al Sole, then the more personal feel of Alterio—this is a solid pick.

FAQ

What time does the Chianti & Supertuscan tour start?

The tour starts at 10:00 am.

How long is the tour?

It runs for approximately 6 hours.

Is lunch included?

No. Lunch is not included.

How many people are in the group?

The group size is up to 8 people.

Do I need to be a certain age to taste wine?

Yes. The minimum age to taste wine is 18.

Where does the tour begin and end?

It begins at Lungarno Amerigo Vespucci, 26n, 50123 Firenze FI, Italy and ends back at the same meeting point.