Tuscany: Small-Group Wine Tasting Tour with 2 Wineries & Local Flavors

Summary

Tuscan vineyards wine tasting two estates local specialties included

You’ll taste Chianti wines at two family-run estates near Florence, sample fresh olive oil on rustic bread, and snack on local cheese and cured meats under Tuscan sun. With a friendly guide handling all transport and stories along the way, you’ll get both vineyard views and real flavors—plus those small moments that linger long after you’re back in town.

What’s the experience like?

The first thing that happened was I dropped my phone between the seats of the minibus—classic me—so I missed the start of our guide Luca’s story about Chianti wines. He just grinned and waited while I fished it out, then picked up right where he left off, telling us how every hill around Florence seems to have its own grape personality. The drive itself felt like a slow exhale after city noise: cypress shadows flickering on the window, patches of wildflowers along the road, and this faint scent of warm earth that I swear you only get in Tuscany after a night’s rain.

At the first winery (I think it was Casa Emma?), we wandered through rows of vines—someone behind me kept brushing their hand over the leaves—and ended up in a cool cellar that smelled like wood and something sweetly musty. The owner poured us three different reds; my favorite was the Riserva, which tasted almost peppery at first. We tried olive oil too, straight on bread. I’m not sure if I’ll ever find that exact taste again back home. Luca joked about how Italians judge each other by their bruschetta technique (mine got a laugh for being “very creative”).

The second stop was just a short ride away but felt like another world—more open hills, sunlight bouncing off old stone walls. We sat outside with platters of cheese and cured meats, and honestly? The pecorino with honey might’ve been my highlight. There was this moment where everyone went quiet for a second, just eating and looking at the view—vineyards rolling out forever, little villages tucked into folds of green. It’s hard to describe without sounding cheesy (no pun intended), but it felt good to be there with strangers who were all just as content to sit and soak it in.

I didn’t expect to feel so relaxed on a day trip from Florence—usually tours make me restless—but something about having time to wander between tastings or chat with Luca about his grandmother’s pasta made it different. If you’re thinking about booking this small-group wine tasting experience in Tuscany, maybe don’t overthink it. Sometimes you just need someone else to drive while you watch the light change over the hills.

Step-by-step itinerary

Day 1 — Tuscan wine country tour and tastings

• Drive through Tuscan wine country
• Stop at first winery for wine and olive oil tasting
• Enjoy short countryside ride
• Visit second winery for cold cuts and wine pairing

Top questions

How many wineries do we visit on this Tuscany wine tour?

You visit two different wineries during this small-group tour.

Is lunch included in the wine tasting tour?

You’ll have local Tuscan specialties like cheese, salami, cured ham, and bruschetta paired with your tastings.

Does this tour include transportation from Florence?

Yes, air-conditioned transport from Florence is included in your day trip.

Are vegetarian or gluten-free options available?

Yes, vegetarian and gluten-free options can be arranged if you mention it when booking.

What types of wine are tasted during the tour?

You’ll taste reds typical of Chianti: usually Chianti Classico, Riserva, Super Tuscans or Gran Selezione.

Is there an age requirement for joining?

The minimum age is 12 years old; drinking age is 18 years old.

How big is the group for this wine tasting experience?

The group size is capped at 25 people maximum.

Will we meet actual winemakers or locals at the estates?

You’ll meet estate staff or owners who guide tastings and share stories about their wines.

What’s included

Your day includes guided visits to two different Tuscan wineries near Florence with tastings of three wines and olive oil at each stop, plus generous platters of local cheese, salami, cured ham and bruschetta—all paired thoughtfully. Transport by air-conditioned vehicle is provided (with free Wi-Fi onboard), led by an English-speaking guide who keeps things lively throughout your small-group experience before returning you to Florence in time for late lunch or evening plans.