Florence: Night Bar Crawl & Dark History Walking Tour

Summary

Florence after dark with wine windows, Medici secrets & new friends

You’ll sip local wine by the Arno as golden hour hits Florence, hear wild Medici tales from your guide, try limoncello through a centuries-old wine window in Santa Croce, and end your night laughing over cocktails on Via de’ Benci. Expect new friends, strange history, and those little moments you’ll remember long after leaving Florence.

What’s the experience like?

You know that feeling when you’re standing by the river in Florence and the sky’s just starting to go gold? That’s where we kicked off — in this little park near the Arno, wine in hand, listening to our guide Marco tell us how the Medici family basically ran the city (and got away with some wild stuff). The air smelled like grass and something sweet from a bakery nearby. I kept getting distracted by the skyline — domes and towers catching the last sun. It felt like everyone else was just passing through while we were in on something.

We crossed over the river (I still can’t pronounce “Ponte” right) and wandered through an alley that Marco said used to be one of Florence’s busiest brothel streets. He told us a story about a nobleman who faked his own death here — I’m not sure if it was true or just good theater, but it made me laugh. First bar stop: a tiny place with shelves of dusty bottles and locals who barely glanced up from their cards. My Negroni tasted stronger than usual, maybe because I was trying to keep up with two Australians at our table.

The Santa Croce district was buzzing — scooters zipping past, people shouting across piazzas. We stopped at this little window in a stone wall (Marco called it a “buchetta del vino”) where you literally get handed a shot through the hole. Limoncello for me; it burned but in a good way. There was this moment when everyone went quiet except for some church bells somewhere far off. I didn’t expect to feel so connected to strangers after just an hour or two — maybe that’s what sharing weird history and drinks does.

By the time we reached Via de’ Benci for our last cocktail, my feet were tired but I didn’t want it to end. The street was alive — music leaking out of bars, someone singing badly in Italian nearby. Our group lingered longer than planned, swapping stories about home and half-remembering Medici scandals Marco had mentioned earlier. I still think about that view over the river at sunset — honestly, it sticks with you more than any postcard ever could.

Step-by-step itinerary

Day 1 — Florence bar crawl and dark history tour

• Meet at park by Aldo river
• Drink wine and learn Medici history
• Cross river and pass busy brothel
• Enjoy Italian cocktail at local bar
• Walk through Santa Croce district
• Take limoncello or amaro shot
• Visit Santa Croce church for history
• Drink cocktail on Via de’ Benci street
• Socialise with fellow travellers

Top questions

How long is the Florence bar crawl tour?

The guided bar crawl lasts approximately 3 hours.

Are drinks included on this Florence nightlife tour?

Yes, wine, two cocktails, and one shot are included during the tour.

Where does the tour start?

The tour begins in a public park next to the Arno river in central Florence.

Is there a local guide on this tour?

Yes, you’ll be led by an expert local guide throughout the evening.

What neighborhoods do we visit on this bar crawl?

You’ll explore areas near the Arno river and walk through Santa Croce district.

Is food included on this tour?

No meals are included; only alcoholic beverages are provided during stops.

Can I join if I don’t drink alcohol?

The focus is on alcoholic drinks; non-alcoholic options aren’t specified.

Is pickup included for this Florence bar crawl?

No hotel pickup is included; you meet at a central location near public transport.

What’s included

Your evening includes all alcoholic drinks—wine by the river at sunset, two classic Italian cocktails at local bars (one near Santa Croce), plus a shot served right through an old wine window—alongside stories from your friendly local guide as you stroll between stops with fellow travelers before ending late-night on lively Via de’ Benci.