Italy (2026) - Piacere — Of The Traveler

Day 0 - Of Booking Vacations While on Vacation

Back in 2025, while we were visiting Austria and Prague, our friends Erin and Brian invited us to join them in Italy. We said yes, because of course. Little did we know that in between that trip to Austria and this trip to Italy, we would visit Spain twice for a few days. I didn’t write about those trips because, although they were great, we were there for a specific purpose.

Booking a trip a year in advance has its perks; there's plenty of time to space out expenses. research, and only builds anticipation. So far, the only downside of this trip is missing a wedding.

The plan is to be headquartered in Florence, take day trips to the surrounding cities, and spend a weekend in Venice. Although we’ve been to Florence with Johannes and Raquel, it didn’t matter; Florence is awesome.

In the meantime, as I did for Austria, I decided to try my hand at learning a little bit of Italian. I’ve been using the Babell app, and I hired a private tutor for help. Oddly enough, I’ve found German to be easier to learn than Italian. It’s easier to speak Italian, for sure. But I feel that I remembered more vocabulary outright with German instead of relying so much on my Italian and my Spanish.

We’ll see how it goes.

If this is your first time here, piacere!

Day 1 - Of Planes and Expectations

I’ll make this section quick since it’s not terribly exciting. We flew on ITA Airways, both our flight from Miami to Rome, and then Rome to Florence went very smoothly. As we pulled up to our Airbnb in Florence, Erin, Brian, and Adrian were waiting for us outside - like a bunch of tourists. Turns out they’d only arrived just a few minutes before us.

The flat is very nice, with four bedrooms and two bathrooms. Once we settled, there was a mandatory nap. All of us were kind of exhausted. Even though I’d slept decently well on the plane, that’s never the most restful sleep. I will give a shout out to the TRTL travel pillow. That thing cradled my neck and held it in place while I slept, it was great. I think I would have slept better if I didn’t suffer the curse of always having someone next to me who keeps their TV on at full brightness.

Afterwards, we went out to the city and walked around. Some places looked familiar, but even in the last two weeks, Florence has changed a little. I saw a lot more closed shops, and a couple of restaurants we’ve visited previously were not shuttered. No matter how static you think a city is, it’s constantly changing and moving. We ended up eating at Trattoria La Madia, it was empty when we arrived, but we gave them some grace since it was 6:00 PM after all. Still, the pizzas, gnocchi, Aperol's, and steaks were all great. I love Italy and its food.

I spent close to six months trying to learn some Italian, unfortunately, no one else knows much Italian, and now I feel a little pretentious using it. There’s a measure of discretion I am using so as to not seem like I am trying to show-off. Still, it’s been great speaking full sentences and going back and forth with the people I’ve met so far and speaking in their native language.

I am not sure what tomorrow brings. Erin and Brian have things they want to do, I have a few ideas, but I am enjoying this passing feeling that I am just happy to be here with no expectations.

The week ahead does have some things planned; wine tasting, truffle digging, gnocchi cooking class, Venice trip, Pisa/Lucca trip, wine windows, etc.

Alla prossima! Ciao!

Day 2 - Of Hidden Treasure and Hidden Soccer Fields

Unsurprisingly, we all woke up late. And by late, I mean 10:00 AM. Understandably, we are all still engaged in combat with jet lag.

As per tradition, or tradizione as they say - I took my morning walk, Brian joined me while we visited Pasticeria Buonoamici, a small bakery about six minutes away from our place. Inside, everyone is Italian; definitely a spot where the locals get their morning coffee and pastry. I ordered croissants and coffees, in Italian - feeling a bit accomplished by this. The pastries were all very good, not amazing, but still above what you’d find in a more touristic area.

The day was lazy; we stayed on the south side of the river, an area that is not touristic, but more local. As we walked, we did some geocaching. This was an introduction to geocaching for Erin, Brian, and Adrian. The kids loved it. We also visited the Piazza de Santo Spirito and meandered the stalls that had been set up.

After our second geocache, we stumbled upon a park. In this park was a mini-soccer field where a bunch of kids were playing. Adrian ended up joining them, looking like he was playing among giants. It felt nice to be in a space that was meant for locals, as if we had just trespassed into a safe space and took refuge from the hustle and bustle.

Once done, we went to Gustapizza. This pizzeria appears to belong to a group of restaurants nearby, Gustapanino & Gustaosteria being the other two. These pizzas were delicious; I went for my baseline 4 Cheese. Whereas pizzerias go heavy on the gorgonzola, making for an uneven taste. This 4 Cheese at Gusta was well balanced. It could have used a tad more savoriness, but still a solid entry.

We slowly walked back to the flat, and had a bit of a siesta before getting ready and heading out to have dinner. We ended up at a very nearby place called Rhione Brewpub. There, we had pasta, and it was good. The thing about places like Florence, or I suppose Italy in general, is that everywhere you go, the food is pretty great compared to its counterpart in the US. So, although my cacio e pepe wasn’t the best I’d ever had, it was still remarkably good compared to what I’ve had in Miami.

At night, I ended up falling asleep for 35 minutes in Luna’s bed, but then we stayed up until around midnight.

Tomorrow, we’ll be headed to the Galeria de l’Academia.

Day 3 - Of David and Wine Windows

I began the day with a solo walk to the bakery, opting to return to Buonoamici. The plan for today is to visit the Galeria de l’Academia. I want to preface this segment by telling you a story. Last time we visited the Galeria de l’Academia, it was with Johannes and Raquel. The statue of David, a quintessential work of Renaissance art, stands at the end of an arcade and a lighted vestibule. It’s magnificent. But the first time I ever saw it, standing just about 30 feet from David, was Johannes taking a photo of David’s penis. This time around, Johannes wasn’t there, but his spirit was felt.

After seeing David, we meandered around the gallery, but the kids were quickly done with the whole thing. Especially since an old Italian woman who worked in the gallery yelled at Luna, then at Cynthia for being too close to some old musical instruments under glass. After seeing some of the art, we left the gallery.

While in Florence's city center, we made our way to a sandwich shop aptly named “Panini Toscano.” It was delicious; they let us taste the different breads, cheeses, and meats you could use to make a panini.

After lunch, we went back to the apartment and relaxed. But before we did, Erin and I visited a wine window. It’s essentially a tiny window in a wall - you ring the bell, they open the window, you tell them what wine you want, you tap your card, and out comes a cup of wine. Not too shabby. We plan to do these a bit during the trip. I took a nap. Mmm naps.

In the evening, we met with additional friends from Richmond.

I’ve been enjoying the pace of this trip; we do a few activities in the late morning, then relax in the late afternoon, and then go back out into the town in the evening. We are all still struggling with jet lag; staying up late and then not waking up again until 10:00 AM.

Staying outside of the main city center has been fantastic. The times we’ve ventured to the main city center, the number of people there is dizzying. Yet where we are staying, there are still tons of restaurants, bars, and cafes, without being crazy packed.

I will mention that it’s been weird, yet pride-inducing to see Luna walking around. She’s not looking like a baby, or a toddler, but her gait, her attitude, and way of being; she’s a little lady, growing up quickly before us. I am trying to appreciate the moments before it all passes by too fast.

Tomorrow we are visiting Boboli Gardens. Ciao!

Day 4 - Of Boboli, not Boboli

In the morning, we woke up late again, but before anyone got up, I snuck away and walked to Wild Buns. Despite the name, this is not some lewd establishment, it’s a Scandinavian Bakery. The last few days I’ve passed by, there’s always been a long line to get in. Today, I wasn’t in a rush, so I stood in line, and oh boy, I was surrounded by Italians. I felt a little out of place, which did further my appreciation for people who don’t speak or understand English well.

Inside, I order two cinnamon buns, and two other buns that were just fantastic.

In the latter part of the morning, the whole group went to Boboli Gardens, which is attached to the Uffizi gallery. Large portions were under construction, which was a bit disappointing, but the parts that weren’t were quite nice with sprawling panoramic views of Tuscan countryside. The walk around the gardens were occasionally arduous, with inclines - Luna decided that she was not interested in walking, so I had her piggy backed on me during the ascents. Good thing I was hyped up on Scandinavian carbs.

Afterward, we took the long walk back home for leftovers and naps.

Later, we all went to Pizza Positano, a small upper-scale pizza place. I, of course, had 5-cheese pizza. It was delicious, but so far none of the all-cheese white pizzas have not wowed me. Even though they have been very good, they’ve all missed a sense of saltiness that I’d expect from a white-pizza. I’ll keep searching.

Erin and I have continued to drink wine.

Tomorrow we are going on a food tour!

Ciao!

Day 5 - Of Food Tours & Ribeye

Dear reader, you may or may not know that I fancy myself to be a good chef; but especially a chef who excels are making great steaks. We knew tonight we’d be making a meal instead of going out to eat, so I offered to purchase and cook the steaks.

First, I went to a local butcher who is considered one of the best butchers in Florence. The man spoke no English, and I spoke some Italian, but in the middle, I was able to order about 3 kilos of rib steak, or as Americans know it, Ribeye. I got thick cuts, and they were amazing.

I'll reveal my recipe for you, don’t tell anyone.

First, I wrapped the steaks in a paper towel and left them in the fridge. Usually, I’d allow 24 hours to dry, but that’s not possible for today; we’ll go with at least 8 hours.

As the steaks dried in the fridge, we made our way to our Food Tour Across the River by Eating Europe. We met Elisa, who was a phenomenal guide. We went to some great spots:

We went to an amazing cheese spot, Sandro & Ivana, or locally known as “The King of Cheese.“ Amazing, the different cheeses we tried were so good. I ended up getting a fresh sheep ’s-milk cheese, one made with wine, and a cheddar for Luna.
Secondly, we went to ‘l Trippaio di San Frediano. So, you may be wondering what this is. This is what’s called Lampredotto: sandwiches made with the meat of the cow's fourth stomach. In a sandwich, it’s delicious, but when you look at it before the sandwich, it looks super gross. To be honest, I loved it.
Our third location was Buonoamici, which, coincidentally, is the bakery I’ve gone to twice already on this trip. Our guide said this is one of the best bakeries in Florence; so….I nailed it. I chose wisely. They prepared for us Millefoglie, and it was amazing, it was like an Italian Baklava.
Then we were taken to Fiaschetteria Fantappie, a hole-in-the-wall spot where we enjoyed a glass of wine and a stew that was good, too. At this point, we were beginning to be full. They had a great wine selection.
Gelateria Artigianale La Sorbettiera - We’ve had a few different gelatos at this point, but oh boy, this one had Italian Sea Salt gelato, and I was in love with it.

All in all, the tour was fantastic, and Luna took to the guide so much so that they walked around hand-in-hand.

After the tour, we went back to the flat and relaxed. At that point, I took the steaks out of the fridge, unwrapped them from the paper towel, and poured salt on them. The purpose of this process is to brine the steak, pulling the moisture from the steak, keeping proteins on the surface, and sucking the salted moisture back into the steak.

After a rest, we went to Kevin and Charlene’s flat, friends of friends, and there, I made the steaks, Cynthia made dessert, and Kevin made veggies, and it was an amazing deal. What’s fun about their flat is that it had large open windows to the river, and we imagined the smells coming out of our window and people looking up and thinking, “I want to eat that.”

We hung out and talked over food, which is one of the best experiences of life.

Tomorrow we have a chill day of walking around Florence.

A presto.

Day 6 - Of Meandering

Erin and the others went on a trip to go truffle hunting. The ones who stayed behind were the three of us, plus Brian and Adrian. Did we have much in mind? Not really. We had loose plans to visit Ponte Vecchio and the leather market, but that was about it. In route we would try and hit up some geocaches.

Yesterday, we told Luna that Ponte Vecchio is a bridge that’s full of jewelry stores. She only listened to only a part of that statement. When we arrived, she looked around and said,

“Papa, where’s the jewelry?”

“Umm, look around, baby, there’s a bunch of jewelry stores all around us.”

“Ugh. But Papa, I thought there was going to be jewelry on the floors and everywhere for me to grab.”

Needless to say, Luna was disappointed.

We walked over the bridge and found a geocache for the kids. We swung by the leather market, which was steps away from the apartment we stayed at last time. Florence has a lot more people here now than when we were here three years ago.

After, we walked and explored the square outside of Uffizi Gallery. From there I found a sandwich shop we’d went to last time, enchanted by the older woman who engaged us in conversation. This time, she was not there, but the sandwiches were still fantastic.

From there, Brian and Adrian took off to go play soccer, while the three of us went to do another geocache. This geocache was associated with a famous Florentine Rock Band called LITFIBA. The geocache was located across the road from a cellar they used for rehearsals. Unfortunately, someone had stuffed the cache was into a hole in the wall and we weren’t able to retrieve it.

Still, in this part of town there was lots of art on the walls, and in general Florence has a penchant for artistic expression in places you don’t expect.

Later, we joined Brian and Adrian for soccer and headed home.

That night we, met up with everyone and ate Gustapizza on the steps of a church looking over a square.

Tomorrow, the three of us are breaking off from the rest of the group and we are visiting the medieval city of Certaldo Alto.

Day 7 - Of Stepping Back in Time

The group at large was going to climb the Duomo in Florence. Instead of that, the three of us took a train to Certaldo, a city just north of San Gimignano and Siena. I found this city through ChatGPT and it checked all the boxes for a day trip from Florence.

When we arrived, the more modern Certaldo Bassa was a more modern city with it’s typical Italian flare. But after a quick walk, we made our way to the funicular and road up to Certaldo Alto, a city/village set atop the hill over Certaldo Bassa.

Immediately we were hit by the antiquity of this place. All the buildings were made of bricks. Then, to add to this allure, it was empty; no tourists, a few locals, and us. It’s low season and it was a random Wednesday morning. Luna showed a fascination with the place that we were not expecting, but we loved. She wanted to explore and check things out.

A main attraction to this place has to do with the Giovanni Bocaccio home. Bocaccio is an Italian poet and author, who some say is the father of the Italian language. He wrote Decameron, a book that’s been translated into many languages, and is considered a pillar of Italian literature.

Also in Certaldo, there’s a Governor’s House. What’s interesting about this particular place is that they’re not sure when it was originally built, but what helps to identify some timeline is that many of the governor’s had their crest affixed to the exterior walls and in some of the internal spaces. Additionally, many mayors from the surrounding areas under the rule of the governor also had crests painted into the internal walls, especially meeting rooms.

The house included two prison cells, and what appeared to be male and female dungeons. It was a cool experience made cooler because it was really the first time Luna showed a real interest in something like this, often calling us to look at something she found interesting.

We ate a tiny hole in the wall ristorante that is absolutely delicious; Osteria da Chichibio.

Once we got back into Florence, we eventually met back up with the group.

Tomorrow we are visiting Pisa.

Day 8 - Of The Leaning Tower and Local Veggies

Today, our entire group arrived in Pisa. There was a sense of safety on this trip that wasn’t there our last time here. Pisa is a huge tourist draw, so of course, there are a lot of scammers and pickpockets. Even when you’re coming from the closest train station, there are guys who are in intervals looking at people and often communicating with each other. I even saw a man in the main piazza in a stroller who was checked out every person’s bag.

Erin said she was feeling feisty and would fight someone. I wanted to see it, but alas, no one tried to pickpocket her.

Being back gave me a greater sense of the place. The first time I was here, there was a sense of awe and wonder, and even though there’s still a measure of that, I looked at these buildings for their details and for their place in time.

After a touristy, but tasty lunch, we went to the tower at 1:30 for our chance to climb all the way up to the top. It’s a weird experience climbing the leaning tower. Firstly, there’s nothing inside; it’s just a hollow structure. Once you’re climbing the tower, it’s difficult when you’re climbing against the lean, and significantly easier with it. It’s not something that you can readily see as you’re climbing, but the legs definitely feel it. Up top, we took in panoramic views of Pisa and the surrounding area; it was beautiful to see.

Once done, we took the train back into the city and walked home.

Some of us were hungry, so Cynthia and I went to the local grocer, who is literally our next-door neighbor. We are never quite sure when they’ll be open. They open when they want to, and I love for them.

We got romanesco, kale, onions, pomodoro sauce, and eggplant - enough for at least 7 people. And it came out to a whopping 9 Euro. Went home, and Cynthia and I cooked a delicious Italian-influenced dinner.

We all hung out at the table and shot the breeze over wine and limoncello. There was a fun moment that may not translate to text, but I am saving it here for posterity.

During the conversation, the topic of religion came up…

Brian: “I was promised several raptures, and I really want to see one.”

Cynthia: “No, that would be really bad!”

Brian: “Yeah, I guess you’re right.”

Cynthia: “Besides, they already made a movie about it.”

Everyone: …….

Cynthia: [Makes Claws with her hands] “Jurassic Park!”

Everyone: …….

Me: [Using 100% of my processing power to make the connection between raptures and Jurassic Park]

The Germans: “Yea!”

Everyone: …….

Everyone: “Rap-Tures! Raptures! Not Raptors.”

Erin: [Dies]

Tomorrow we are going to Venice.

Day 9 - Of Venice, the Impossible City, and Conspiracies.

We took a business class train from Florence to Venice. It was a smooth and lovely journey in comfy seats. Arriving around 2:30 PM, we decided to make the 30-minute walk from the train station to San Vio Luxury Apartments.

Last time I was in Venice, it was back in 2000; I was a teenager in my senior year of high school. The skies were gloomy while we were there, and the city flooded every day at high tide. There are a lot of stories that came out of that trip; like my mom booking our train to arrive at 11:00 PM, and us getting lost (No cell phone GPS back then). But there is one story that sticks out among all others.

When we finally arrived at our hotel, the receptionist told us that above all else, we cannot climb to the sixth floor. So, the next morning, the first thing I did was climb onto the sixth floor, where I found a ton of electrical and computer equipment. Someone spotted us and yelled in Italian to go away. One thing we noticed is that all the bell staff were extraordinarily large eastern European men, at one point while at the reception area, my brother and I were joking around about how this hotel was involved in a big conspiracy because everyone was acting so weird. The receptionist heard us and made it clear he had with a cough while staring right at me. From that time on, whenever we passed him by in the reception area, he’d stare at me. Or the large bellhops would look at my suspiciously.

When it was time for us to leave, they told us that they’d arranged for a special taxi for us to the train station. My parents were delighted, I was skeptical. They told us the taxi would pick us up in an alley behind a Chinese restaurant. This is when I started getting nervous.

Eventually, the taxi arrived, and despite there being enough seats for us outside of the cabin, the driver left our luggage outside, and he stuffed us all into the cabin, and LOCKED THE DOOR FROM THE OUTSIDE. That’s when I confessed to my parents about the conspiracy theory. So for 20 minutes, we were all kind of freaking out inside this cabin, and my folks were furious at me.

When we finally arrived at the station, we were relieved. I was the last to leave, and as I did, the drive said in broken English, “you shouldn’t talk so much.”

Now I am back in Venice! A bit older, a bit wiser. The walk to the apartment was fascinating, it was like stepping back in time to a city that didn’t look like it had advanced. It looked like it had aged, with buildings that seemed abandoned, or in varying phases of disrepair. Still, there was a sense of beauty to this place.

Then, when I began thinking of where we were and where this city is, I couldn’t help but think that this city shouldn’t exist. Who builds a city on top of a muddy swamp in the middle of a lagoon? They did. And it’s survived for centuries, with some buildings in the 600s of years old. There’s an otherworldliness to it all, this impossible city built on wooden piles dug deep into the mud, sitting atop the water. I loved it. Everywhere you turned there is something interesting to see. It’s true, if you go fast, you’ll miss it all, you’ll get lost and be frustrated with this place, but when you go slow, linger, and look up, this place has a charm that very few cities have had on me.

We had gelato for dinner as we walked around at night, seeing some of the sites my Italian tutor, Laura, had mentioned.

It was beautiful.

Day 10 - Bridges and Lagoons

We woke up slowly, the plan for today was to check out some places and enjoy the city. Beginning with Punta Della Dogana, the tip of the peninsula we were currently on. It was a nice spot with expansive views of the lagoon and several part of the city, all in one.

From there, Cynthia, Luna and I hopped onto a gondola, where we had a nice 30-minute tour of some of the smaller canals of the city. Despite all the people around, or rather, all the tourists around, there is a sense of loneliness to this place. One street is packed with people in Patagonia puffer jackets, while a street over, it’s desolate. It turns out, Venice only has about 50,000 residents, whereas back in the mid 20th century, the population was more into the 100,000s. The problems inherent to living on a floating city are apparent here, plus the cost of living, has forced many to leave, which in turn has made many business like groceries, doctors, schools, etc to also close, where more touristy spots open. Slowly, Venice will become another Disneyland like central Florence is.

After the ride, we ate lunch, where Brian and Adrian left to catch a Venice soccer match.

The rest of us walked around a bit, did some shopping, then took a rest. At night we had dinner at Ristorante Rafaele, a place that’s been in operation for 70 years. It was all declicious, I finally had my black ink pasta!

In our journey in Venice, we’ve visited Ponte Accademia, Ponte Rialto, Punta Della Dogana. But really, it was just the wandering that was amazing.

I loved Venice.

Tomorrow, we head back to Florence.