In my first three months of full-time travel, I didn’t go anywhere that I had visited previously. Each destination was brand spanking new. Then came Florence. My first time in Florence (and in Italy) had been two years prior, alongside one of my favorite travel companions – my brother. As such, I didn’t feel the need to plan a lot of tours or book a bunch of restaurant reservations. I just wanted to wander the city and enjoy myself.

It was also the first time in the last three months of hotel stays that I’d be staying in an Airbnb (aside from Lindsay’s bachelorette party). For my first visit to Florence, I stayed in the opulent St. Regis, but this time I wanted something more modern and relaxed. I found this charming apartment that looked like a calm oasis in the thick of it all.

Florence Day One

From my apartment, I walked out on to the busy streets of central Florence
But I could still enjoy a peaceful nightcap on my private jasmine-scented terrace
By the time I had settled into my apartment it was already aperitivo hour. I booked it to Caffe Gilli for a Negroni
Dinner on night one: pizza at Santarpia – yum
The Duomo is always a breathtaking site, but I find it to be the most alluring at night when the crowds have dispersed and the delicately intricate buildings are lit up against the dark night sky.

Florence Day Two

My second day in Florence got more interesting.

Ponte Vecchio reflections during my morning run
Lunch at Gucci Osteria da Massimo Bottura. Yes, it’s a tourist trap, but I had to do it.
Gucci AND Massimo Bottura? In Florence? Couldn’t skip that winning combo.

My post-lunch plan was simply to walk around, work off my mid-day wine and risotto, and see what I found. The first notable event occurred when a friendly older gentleman approached me. After greeting me in Italian and quickly realizing that I did not speak more than a few cursory words of his primary language, he switched to English. “You are visiting? Where from? Ah, New York! How long are you here? Would you like to get a coffee?” He was dressed in a suit and seemed like a respectable fellow, but he was also old enough to be my father – at least. I awkwardly told him that I was in a hurry and turned down the next side street. Yep, I was in Italy,

The happy ending to that somewhat creepy story is that I stumbled upon a local clothing boutique. Co. Ar. U had the rare combination of pieces that were locally-made, trendy and affordably-priced (but not cheap-feeling, if you know what I mean). The staff was extremely sweet and I left with a dress, a top and a jumpsuit. My suitcase was already packed to the brim, but I’d find some room for my new Italian wardrobe, damn it!

Next I headed to La Terrazza Continentale, a rooftop bar at the hotel of the same name (recommended by Gina). The people-watching was incredible. The dude on the left started smoking out of a pipe at one point and the woman in glasses in the right corner was decked out in every single designer label you could imagine. Prada sunglasses, Cartier bracelets, Rolex watch, Hermes belt, Gucci bag… that’s just the beginning.
The terrace also had a picturesque view of the Ponte Vecchio, but I found the people-watching to be the defining feature of the place

After a Negroni on the terrace, I headed back to my apartment to rest, freshen up and change. It was early June in Florence and it was getting hot out. I decided that my new long red dress would be the perfect attire for my last evening in Florence.

I found a wine bar, Sei Divino, for a pre-dinner drink. Neri, the sommelier, took a liking to me, and offered no shortage of wine tastings. I eventually had to leave for dinner, but had no doubt that Neri would welcome be back later if I so wanted.
Dinner was at Caffe dell’Oro in the Portrait Firenze hotel. Once again, I delighted in the people-watching. There was this couple – the man looked to be much older and the woman seemed quite icy, if you can’t tell from the picture. I entertained myself with outlandish imaginary stories about their relationship, in the spirit of my good friend Heather.
There was also this group of dudes. One of them wore sunglasses the entire meal. Maybe he was some kind of celebrity? Maybe he was just weird? Both? No clue.

The weather was quite pleasant after dinner, so I decided to take a stroll along the Arno River before calling it a night.

Nighttime reflections of the Ponte Vecchio

It was Monday, so I didn’t expect to see too many people out, but I met a large crowd lining the river and bobbing their heads to the pulse of an electronic music show. Hmm, this seemed interesting. I decided to stick around and see what was going on.

“Hey! I remember you from the wine bar earlier!” I turned around as a man I’d never seen in my life smiled back at me. “I remember your dress!” Oh, my new red dress was already winning fans. “Are you by yourself? I’m with my coworkers if you want to join us for a drink,” he told me. “Men and women,” he added, taking note of my dubious look.

What the hell. It was my last night in Florence and I might as well enjoy the unexpected Monday night music show a while longer. I introduced myself to the work group as they handed me a Sambuca. When in Italy…

Then, a fireworks show started. WTF?!

My new Italian friends were as dumbfounded as I was about all the commotion. They were each visiting from different parts of Italy and confirmed this wasn’t a national holiday of any kind. Yet, people were out in droves, the fireworks and music rivaled the 4th of July in many major cities in the US and the party didn’t seem to be anywhere close to ending at 11pm. On a Monday.

I never figured out exactly what the big deal was. If you ever find yourself in Florence on June 24th, you can check out the San Giovanni festival, which also includes fireworks and sounds like a blast (literally and figuratively). But I was two weeks early for that party. I really can’t tell you what was happening, but it was one of those serendipitous travel moments that I wasn’t going to question too much.

When the show finally ended, I bade farewell to my new Italian friends (my red dress admirer wanted to stay out for another drink, but I was NOT interested) and continued on my own merry way. The following day I was taking the train to La Spezia for my first visit to Cinque Terre!

My visit to Florence ended with a bang