*These events took place in September 2025.
*This post is very long, so if it is cut off, be sure to click “View Entire Message” at the end.
“Wherever you go becomes a part of you somehow.” – Anita Desai
Twenty-three years ago, I visited Florence for the first time. I was studying abroad in Prague, and during our stay, my roommate and best friend, Squint, and I did a 10-day whirlwind trip through Italy, hitting all the hot spots…Florence included.
The moment I stepped off the train, I was in L.O.V.E., and I swore to myself and the heavens above that one day I would live there and drink espresso at the cafe counters, and stroll the cobblestone streets while speaking fluent Italian. That hasn’t happened (yet – I need a miracle given the damn government rules and regulations), but I do still have the silver necklace that says “LOVE” in a Chinese character that I bought on that first trip. ❤️ Clearly, destiny is working overtime. Because somehow, I just keep returning to this charming Tuscan town…despite the 90-day rule.
After dropping our bags at the hostel, we headed straight to the crown jewel of Florence – Cattedrale di Santa Maria del Fiore (aka, the Duomo). In my opinion, it is by far one of the most beautiful cathedrals in the world – especially now that years of careful restoration have removed centuries of soot and grime from the marble facade. It’s like she’s had a glow-up – all shimmery and shiny with her bad self.
Construction on this magnificent structure began in 1296 and was largely completed by 1436. Filippo Brunelleschi was the genius architect behind the engineering of the incredible dome. It is the largest brick dome ever built and uses an innovative self-supporting double-shell design.
Renaissance men (and I’m sure many women were doing important things behind the scenes, too) were out there solving problems and building beautiful structures without Google and AI. Can we have a Renaissance period again, pretty please?
The bell tower next door was designed by Giotto di Bondone. It stands 227 feet tall (84.7 meters) and has exactly 414 steps to reach the top. Four hundred and fourteen steps that I did not climb (I’ve paid my dues before), but Ingeborg and James did. Teamwork makes the blog work, and thanks to them, you get a stunning sunset view of Firenze without me sweating and hyperventilating on a staircase.
We also visited my friend Simone, whom I met in 2021 when I spent a month in Florence. What started as a simple shopping interaction turned into a genuine friendship (read more about that trip here). Despite our differences, me, a white woman from America, and Simone, a younger man originally from Lebanon, building his life in Italy, we’ve remained connected. We don’t see each other often, but we keep in touch via text and support each other’s business social media platforms, and whenever I’m in Florence, I stop by his shop to say hello.
Simone has been wonderful, not just to me, but to many of my friends who have purchased a leather good (or five) from him over the years. This time, I bought a duffel bag for my dad’s birthday, and as always, Simone took great care of me. He even handled all the packaging and shipping details – grazie mille!
Simone is an immigrant who has seized opportunity with both hands – learning the language, forming relationships, and building his own personal empire. Since we met, he’s opened his third leather store and now owns a golf cart tour company called Florence Panorama. I’ve never met an entrepreneur like him…he is incredible.
In addition to his leather business and tour company, Simone has also purchased and remodeled a beautiful two-bedroom, one-bathroom Airbnb apartment. So, if you need a place to stay during your visit, check out his lovely accommodation just outside of the city center in Florence.
If you are unable to visit Florence and desperately need buttery-soft Italian leather in your life, you can order from him directly via his website – simoneleather.com.
As a generous gesture, he arranged for one of his drivers (and photographer extraordinaire) to give us a private tour of the city, including a long stop at Piazzale Michelangelo for sunset – all free of charge. That’s just the kind of guy he is.
It was just a tad crowded on the stairs for Mother Nature’s closing act of the day. Yikes! And a beautiful couple was there (with 200 of their closest friends) for wedding photos. Lots of cheering and clapping happening on those steps.
Now. Let’s talk about priorities.
Bring on the booze.
The tippy-top item on Ingeborg’s Firenze bucket list? Buying wine from one of the famous wine windows.
If you haven’t heard of these tiny portals to vino (and occasionally gelato) heaven, allow me to enlighten you.
Here is my research from the internet:
Wine windows (Italian: buchette del vino) popped up in 16th-century Florence during the reign of Cosimo I de’ Medici. In 1559, he permitted noble families to sell wine from their country estates directly to the public, knocking out the middlemen and extra taxes. Customers paid less, aristocrats earned more, and tiny arched openings, buchette del vino, were carved into palace walls to serve wine straight to people walking along the street.
These little holes in the wall were especially useful during 17th-century plague outbreaks (think: the Bubonic Plague of 1665 that spread from London & the Plague of Italy), functioning as an early version of contactless service: wine passed through the window, and coins were collected on a vinegar-sanitized metal tray.
Today, about 150–180 of these charming little windows still exist in Florence, with a few more in towns like Siena and Lucca. Many were sealed up over the years, but during the 2020 COVID-19 pandemic, some reopened to serve drinks and gelato, reviving a Renaissance tradition. The Associazione Buchette del Vino now helps preserve and document them, ensuring this small but delightful piece of history lives on.
Inge was extremely pleased with her purchase. As one should be.
Since I’ve already seen Michelangelo’s masterpiece, the statue of David at the Galleria dell’Accademia di Firenze, at least five times, I saved €25 and sat out this stop on the tour. James and Ingeborg went and were appropriately impressed. But honestly, who doesn’t appreciate a 17-foot-tall nude marble man who can’t interrupt you?
I also skipped out on the visit to the Uffizi Galleries for the same reason.
Been there. Admired all the beauty inside. Will go again at a later date, probably.
James sent only photos of nude women for the blog – because of course he did.
The Birth of Venus by Botticelli and Venus of Urbino by Titian.
Affogato (meaning: to drown) from Vivoli Affogato Bar is my new favorite dessert. Gelato drowned in espresso. Ummm, yes, please.
I cannot believe I waited this long in life to try it. Honestly, what have I been doing with my time?
We spent several days in Florence. On our last day, Inge and James went to Siena for a Tuscan wine tour while I stayed behind for a much-needed pedicure to repair my worn-out footsies after hiking 600+ miles of the Via Francigena.
And no, do not get any entrepreneurial ideas about selling my foot photos.
Quick side story:
On my solo day, I met a lovely brother and sister from Canada traveling around Europe. We started chatting at breakfast, and I told them about my hike on the Via Francigena. Alexi was instantly intrigued. Long story short, he changed his plans (with his sister happily continuing to Greece solo), picked up some recommended gear at Decathlon, and set off hiking from Lucca to Siena.
He later sent me some photos and a short recap of his hike and said I could share them with you.
Walking the Via Francigena was incredibly special.
My favorite moments were the quiet sunrise walks alone and a donativo in Gambassi Terme, where a small group of us connected over dinner and made plans to travel on together. The walking wasn’t too hard, though I would’ve needed a rest day if I’d continued.
What stayed with me most were the small, unexpected connections – a man pulling over to talk about his granddaughter, or sharing a cappuccino with a stranger going through a hard time. It was those simple, fleeting moments that meant the most.
I was so impressed and inspired by his willingness to change course and try something completely new – something he had never even heard of before our breakfast conversation, and also by his sister for being so supportive about it and continuing on her journey alone. We could all be a little more like Alexi…and his sister – courageous and flexible!
Bravo, Alexi!
…finally, no Wondering Wanderer trip is complete without a few mirror selfies. It’s tradition!
Florence truly is one of the best cities in Italy…rich history (fun fact: it briefly served as Italy’s capital), extraordinary art, unforgettable food, and architecture that makes you question your life choices back home. If you ever have the opportunity to visit, you must.
Much love & gratitude. Namaste 🙏
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A few final highlights:
Ingeborg had to wear my coat as a skirt to cover her legs before entering the Battistero di San Giovanni (Baptistery of St. John). Shoulders and knees covered. Desperate times call for desperate measures.
James rubbed the snout of the boar at the Fontana del Porcellino. Legend says if you toss a coin and rub its nose, you’re destined to return to Florence. I’ve rubbed it multiple times, which explains everything.
Fun fact, we have a replica statue in Kansas City on the Country Club Plaza. Destiny clearly has a Midwest branch office.
Inge found some cute hot pink (her signature color) cowgirl boots at a thrift store – Humana Vintage Firenze. Renaissance meets Western wear.
We devoured more pasta, pizza, wine, and gelato than I’m emotionally prepared to discuss. I need start hiking again ASAP.
James posed heroically on the Ponte Vecchio like the cover of an Italian Novella. Ladies, he’s available.
Officina Profumo-Farmaceutica di Santa Maria Novella – one of the oldest pharmacies in the world, started by the Dominican friars in 1221…and one of the most picturesque and good-smelling places in Florence.
