Florence: Sunset Food & Wine Tour with Historic Wine Windows

Summary

Florence evenings tasting Super Tuscan wines, cheese boards and gelato in Oltrarno’s lively streets

You’ll wander Florence’s Oltrarno at sunset with a local guide, tasting Pecorino cheeses and bruschetta from historic wine windows, sipping Super Tuscan wines in an ancient cellar, learning about cucina povera over wild boar stew and pasta, then finishing with real artisan gelato under glowing streetlights. It’s more than just eating — you’ll feel part of Florence for an evening.

What’s the experience like?

I didn’t expect the first sip of Prosecco to taste so fizzy after the heat — we’d just landed in Florence that afternoon and somehow ended up clinking glasses in a square where everyone seemed to know each other. Our guide, Giulia, waved at half the people passing by. She told us about these “wine windows” — buchette del vino — tiny holes in old walls where wine used to be sold straight to locals. I’d never even heard of them before, but suddenly there we were, getting handed bruschetta through a stone window by a woman who winked at me when I tried my best “grazie mille.”

The cheese stop was next — two kinds of Pecorino and Parmigiano from this guy they called “the King of Cheese.” He looked like he’d been slicing wheels for decades. The shop smelled sharp and sweet at the same time (I still think about that). We tried guessing which cheese was which; I got it wrong, but honestly, it didn’t matter because everything tasted better than anything I’ve ever bought back home. Then came charcuterie boards in a cellar that felt older than my entire country. The air down there was cool and almost dusty, and the wine — some kind of Super Tuscan — went straight to my head in the best way.

We wandered through Oltrarno’s narrow lanes as dusk turned everything gold. At one point Giulia handed us Negronis (“Florentine invention!” she said proudly) and explained cucina povera while we dipped spoons into this thick Tuscan soup made from leftovers. It was simple but so good — rich without being heavy. Wild boar stew followed (I hesitated but ended up loving it), and then pasta tossed right in front of us by a chef who barely looked up except to nod when someone asked for seconds.

Honestly? By the time we reached gelato (real stuff, not the neon kind), I was full but happy. There was a quick lesson on how to spot fake gelato — apparently pistachio should never be bright green? Who knew. We finished outside under streetlights, sticky-fingered and laughing about our failed attempts at Italian pronunciation. I keep thinking about those little moments: the clang of glasses echoing off old stones, or how everyone seemed genuinely proud to share their city’s flavors with us.

Step-by-step itinerary

Day 1 — Florence food and wine tasting tour

• Enjoy Prosecco in lively square
• Taste Pecorino and Parmigiano cheeses
• Visit 1st wine window, taste bruschetta and wine
• Visit 2nd wine window, taste charcuterie and wine
• Taste Negroni, Tuscan soup, wild boar stew, Super Tuscan wine
• Taste Tuscan pasta with Chianti Classico
• Take gelato artisan crash course
• End tour with real gelato tasting

Top questions

How long does the Florence sunset food & wine tour last?

The tour usually lasts around 3-4 hours in the evening.

Are vegetarian or gluten-free options available?

Yes, you can email dietary requirements such as vegetarian or gluten-free diets after booking.

Is this tour suitable for all fitness levels?

Yes, it’s suitable for all physical fitness levels with mostly gentle walking.

Does the tour include alcoholic drinks?

Yes, you’ll taste several wines plus a Negroni cocktail during the tour.

What is included in the Florence food & wine tour?

The experience includes all food tastings (cheese, charcuterie, soup, pasta), 5 wines, Negroni demo & drinking, plus artisan gelato.

Where does the tour take place?

The main stops are in Florence’s Oltrarno neighborhood.

Is transportation provided?

No hotel pickup is included but public transportation options are nearby.

Can guests with severe allergies join?

No; guests with severe or life-threatening allergies cannot participate for safety reasons.

What’s included

Your evening includes guided tastings of five different wines (including Super Tuscans), Prosecco to start things off right, two kinds of Pecorino plus Parmigiano from a neighborhood cheese shop, charcuterie boards served inside a centuries-old cellar via Florence’s famous wine windows, Negroni cocktail demonstration (and drinking), traditional Tuscan soup and wild boar stew at a historic fiaschetteria, fresh pasta paired with Chianti Classico at a trattoria where you can watch the chef work his magic—and finally real artisan gelato with tips on spotting the good stuff before you say goodnight.