Montalcino & Montepulciano: Brunello Wine Tour from Florence

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Free cancellationExcellent quality

1/13

Duration9h

GroupPrivate

LanguagesEN · IT +1

PickupAt your hotel

Two Tuscan Wine Towns in One Day: Brunello Tastings Through Val d'Orcia

You get picked up from your Florence hotel and driven through Val d'Orcia to Montalcino and Montepulciano, where you taste Brunello and Nobile wines directly from producers. The route includes Pienza for a Pecorino cheese tasting and a walk through its Renaissance streets. Lunch and all transport are included, and you return to Florence in the evening without arranging anything yourself.

Step-by-step itinerary

Explore Val d'Orcia and Wine Towns

Pass by Val d'Orcia valley
Visit Montalcino wine town
Explore Montepulciano historic center
Walk cobblestone streets of Pienza
Taste local Pecorino cheese

The Experience

You're standing in a Montalcino cellar, and the producer is pouring a wine that costs more than your hotel room. He's talking about the 2015 vintage—how the summer was dry, how Brunello needs five years minimum in oak—and you realize you have no idea what you're tasting, but you're tasting it anyway. That's the moment this tour lands. The driver picks you up from your Florence hotel in the morning and heads south toward the rolling hills of Val d'Orcia, a UNESCO-protected valley that looks like someone painted it and then forgot to stop. Montalcino sits on top of a hill, walled and medieval, and the whole town exists because of Brunello di Montalcino—a wine made from Sangiovese clones that collectors hunt for. You'll meet actual producers, not just taste in a shop.

After Montalcino, the route moves to Montepulciano, where Vino Nobile di Montepulciano comes from—another Sangiovese-based wine, but different enough that locals will tell you the difference if you ask. The town itself is layered with Renaissance architecture and the kind of narrow streets where you can touch both walls at once. Then there's Pienza, the Renaissance town that Pope Pius II basically designed from scratch as an ideal city. You stop there for a Pecorino cheese tasting—the local specialty—and walk the cobblestone streets that actually feel intentional, not just old. The whole day moves through Val d'Orcia, so you're not just tasting wine; you're tasting it in the place where it grows, which changes how it tastes.

The tour runs with a private guide and driver in an air-conditioned minivan, so you're not crammed into a bus with thirty people. Hotel pickup and drop-off are included, which means you don't have to figure out how to get to Montalcino or drive yourself after tasting wine all day. Lunch is part of the day, and if you need vegetarian or gluten-free options, you mention it when you book. The whole thing is built for wine lovers who want to understand where Brunello and Nobile come from, not just drink them.

What’s included

Your day includes hotel pickup and drop-off from Florence, private transport by air-conditioned minivan, a dedicated driver and guide, visits to Brunello and Nobile wine producers with tastings, a Pecorino cheese tasting in Pienza, lunch with a beverage option, and time to walk through the Renaissance streets of Montalcino, Montepulciano, and Pienza. Vegetarian and gluten-free lunch options are available upon request at booking.

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyInfant seats availablePublic transport nearby

Operated by Let's Andiamo

Is this one for you?Book this if you want to taste Brunello and Nobile wines where they're made without arranging your own transport or winery contacts—the producer meetings and small-group format are what make a day in Montalcino and Montepulciano feel like an insider's visit instead of a standard wine route.