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Italy Trip 2026

Florence, Ravello, Venice· September 2026

September 5–18, 2026 · 19 logs · 3,485 words across 10 days

September 18, 2026


8:27pm

Venice is also a microcosm of friction as a feature in the sense that most anything large or heavy brought in has to be done by boat. And even the boats themselves are limited in width, hull depth by the canals. This means anything transported or built here has to be really intentional.

8:05am

On our strolls through the alleys of Venice we stumble upon this sprawling campo in the heart of Santa Croce. Bursting with life. An expansive courtyard dotted with towering platano trees and centuries-old cisterns. These wells, a reminder of how each campo was built to collect its own rain. Everything that falls here is kept.

It turns out to be where all of the schoolkids assemble at the end of their day — playing tag, chasing each other with water balloons; it’s where one of the handful of markets in the city seems to be; where couples meet for meals and drinks; where hipsters stroll with their cigarettes; where all manner and size of dogs are walked.

We see a tavern and decide to dine there. We sit there long enough to notice the ebb and flow of the courtyard’s energy. We order our food during one of the lulls. Not long after, a well-dressed but slightly disheveled older gentleman strolls up to the restaurant. Our waiter sees him and scampers over to greet him gently. They interact for a bit and then our waiter leaves him and goes about his business interacting with other customers.

A few minutes later, we notice that the man has wandered into the courtyard and has started rummaging through the trash. We haven’t seen a single other homeless person during our time here. We wonder if he is a vagrant, but notice that he hasn’t taken a single thing out of the trash. Our waiter scurries over to him, talks to him again. We try not to stare, but this level of care for a stranger—heck a neighbor—is unheard of in the states, we pretend to ignore the destitute in our country. Moments later the waiter gently brings him back to the restaurant, takes him to wash his hands, and gives him a pile of receipts to fumble with.

When we ask our waiter if he is okay, he responds that his name is Paulo and he is a long-time local, that he has Alzheimer’s, but has no family to take care of him. For a brief moment all three of our nervous systems sync up in sadness. I ask the waiter his name, Nikolai he responds, he says he is from Moldova but went to university in Venice and now he has Italian citizenship. I tell him—holding back my own tears—that we saw what he did, and that not many people back home would have done that, and that it mattered to us and to Paulo, even if he couldn’t say so. He gets overcome with emotion, and excuses himself.

As we eat our food, one and then two women walk through the courtyard and exclaim “Ciao Paulo!” He looks up briefly, energy in his eyes, and nods his head at them. It seems as though the town square has taken in Paulo as one of their own. We ask Nikolai if we can buy him a meal, and Nikolai assures us that Paulo has more food than he could ever need. Turns out Paulo used to own two shops in the town and even though he has no family to look after him, his neighbors in the town are already taking care of him.

After we finish eating, I take some time to reflect on what I saw in the courtyard. I realize this encounter, the way this old man was treated by his community is a microcosm for this trip, and what I’ve learned about Italian culture, and their genuine kindness. Beyond the generosity of so many of the people we interacted with on a day to day basis, I have been floored by how this country treats people it owes nothing to. Because it would be easy to look away. I reinjured my lower back on this trip, and went to the emergency room to be treated. I, an American tourist, walked out of that hospital having been charged less than two hundred dollars for the visit.1. including a CT scan and three different medications Our Airbnb host graciously offered us one of his rooms as many nights as we needed it and charged us a fraction of the cost, checking in daily to ask how I was doing, and if he could help in any way.

A few days earlier, from a letterpress printer a few blocks away, I’d learned that “ciao” isn’t Italian — it’s Venetian, and it started as a way of saying I am at your service. Giving new weight to what I’d heard shouted across the courtyard three times and what I’d been feeling ambiently all week without recognizing it: at the hospital, with that spare room.

September 17, 2026


8:22am

As I’m trying to put together why Venice feels like such a magical place, beyond the fairytale-like novelty that the Venetians loathe being sterotyped for — I think its for actually for its improbability.

That this place was created in the first place. That the city was built more than a thousand years ago with the limited resources and tools that they had back then. That it still exists to this day, that it is still a living, breathing city.

And to walk around the city, and see up close every texture, fabric, stone, sidewalk with such detail and to think that its been around, maintained, lived in for centuries despite nature’s attempt at entropy is something to behold, and can only be fully appreciated in person. Because of its lack of cars, bikes, scooters, (sure, it has small boats but) it’s mostly experienced in person, by walking. These constraints completely change how it feels to move about within the city. And during the “rush hour” (people going to work, taking their kids to school) it feels truly alive in a different way (bursting at the seams with human energy) that than I’ve ever experienced, in that beauty in the chaos kind of way that I’ve felt multiple times now on this trip.

But Venice has internal bleeding. The rush hour is thinning. Driven out by tourism and rising rents1. Me being one of them! — apartments turning over to people who stay a weekend. The very places and people that carry forward the culture and customs are leaving. It held off the water for a thousand years. It may not hold off us. If Venice goes away, it can’t come back. Am I part of the problem?

September 14, 2026


8:33pm

The Naples train station is pure cacophony, the city is feels chaotic but lived in, the same way that Athens felt. Juking in and out of the way of others, we arrive at the food court. There’s a small old wooden piano in the middle of it. An older gentlemen (who doesn’t seem to work there) is manning the piano, another local walks up to him and they briefly exchange pleasentries, agree on a song; not long after I hear the piano playing the singing starts. Emblematic. Taking time in this busy place to embrace and savor the chaos of life. Make fun of it and with it.

September 13, 2026


8:52am

The constraints of a given place become a way to savor the little there is even more. Waking up in this small apartment in Ravello, with its small kitchen, handful of dishes, its tiny moka pot; but that friction giving me that feeling of being so ingrained in the experience, the gratitude of the moment, the smell of the ground coffee, the sound of the bubbling water, the sherbert-colored sunrise on the patio. I could very much get used to this.

September 12, 2026


9:10am

Having stopped in Amalfi midway through my run and come to appreciate Ravello for being and feeling more lived in. Ravello isn’t as touristy because its way harder to get to.

I travel for the experience of seeing good life being lived in other ways than I might be exposed to. And when I think about harder to get to places and experiences are going to become more valuable, because they naturally filter out the people who are looking for the cheaper highs of novelty-seeking.1. And for those of us willing to suffer a bit, the upside is that we savor things more when they’re difficult.

But getting there isn’t the only constraint. Old town Florence is easy to reach and still feels lived in, maybe because it was shaped by the constraints of when it was made.

Mod, writing about how tourism is reshaping Rome:

I keep thinking about the mid-2000s as the last moment of ‘authentic’ tourism to major cities… Now you have to stretch to find those kinds of experiences / interactions. I spent four nights in Rome last month, and … wow … central Rome is rivaling Tokyo for Disneyland vibes.”

And the same problem is gutting Venice. The risk is that it’s going to be deserted by the people that actually live there and make it a city, sooner than it’s going to sink into the ocean. The people who make it a city are the ones who can’t afford to stay.

So how do we not ruin a place with tourism? I don’t think the answer is a policy. When we’re able to articulate what we respect and revere, then you can decide you want to conserve it — but you have to tell stories about it, and tell them to the right people, so that enough of them believe it’s worth keeping around.

8:31am

We absorb the nature of the places around us. I’m on this run along these terraced hillsides on the Amalfi coast, held up by dry-stone walls, planted with lemon groves under chestnut-pole pergolas, and I keep thinking to myself “how could you be mad about life when it’s this good?” It’s far too short to be occupied with control, nitpicking and caring about trivial shit. This is enough. This could be enough. I realize how I’m feeling now is directly proportional to the discomfort I’m putting myself in, is in this run is really challenging, the conveniences and nicities of normal travel are stripped away; but that’s maybe why I appreciate it all more.

September 10, 2026


11:08am

So many restaurants here have no music playing, it’s just conversation and the clinking of plates and silverware. It’s almost like people are afraid of awkward silence in the US. Or they are afraid to be left alone with their thoughts.

10:01am

More unexplainable cultural osmosis: life lived in the moment. Not focused on hyper-optimization, “manifesting”, growth, just living very fully in the moment. In the same way that an impatient driver on the road is contagious, maybe the pervasive growth mentality, the keeping up with Joneses, the bigger and better than you mentality bleeds into our brains (further exacerbated by the social media and advertising hijacking our tribal instincts and reward pathways). I didn’t see any billboards in Florence or Ravello.

7:33am

Taken aback by the size of things here. And Americans’ relationships with trash and waste. Tiny wastebins; our hosts—maybe sensing that we are yankees—tell us that anything we can’t fit in them would have to be deposited in the street-side receptacles. Everything seems more right-sized here; bulk-sized and bulk-buying taking on new meaning. Everything is bigger (but not necessarily better…) in the United States. Bigger portions, bigger groceries, bigger cars (to fit more groceries), bigger ambitions, more consumption, and more trash. So much trash, so much waste.

September 8, 2026


3:53pm

We went to go visit the statue of David today, because it is something you must do when you go to Florence. We forayed northeast across the Arno River to the touristy side of the city. It was 37°C and 80% humidity. We arrived there and saw a line stretching down the block, exposed to the sun, and a mob of other clammy, cranky tourists and decided to abandon our places.

Later that day a timely essay came through from David Cain about bucket lists and travel checklists are not only impractical but are quickly outdated (past versions of yourself, inherited lists from others).1. David found many old goals no longer mattered and thinks lifetime lists are often impractical. Now, he focuses on meaningful personal challenges and relationships instead of ticking off exciting experiences. Then I remembered that other piece I read recently about people who are trying to race to visit every country in the world2. “Last year a record 82 people claimed to have achieved the feat of travelling to all 193 countries.” (and undoubtedly sharing it on social media), and how this pervasive (potentially status-driven) mentality of quantity over quality3. And it’s no surprise that the conveniences, technology of modern travel actually enabled this is so misplaced, and misplaced for the same reasons that this “choosing friction” essay4. “Today’s cult of convenience fails to acknowledge that difficulty is a constitutive feature of human experience. Convenience is all destination and no journey.” talks about: when you forgo friction you miss out on learning the things about yourself, you miss out on the challenges that make these events and occasions meaningful.5. Sweating through your clothes on a walk to a rose garden to re-read our vows on our one year anniversary

As I’ve been feeling on this trip, you miss out on the depth of experience and interaction with others when you don’t choose to go the more meaningful route.6. We wouldn’t have met the couple that runs the pizza shop and the olive oil shop if we were there for a day and only focused on the places that other tourists say we should go. It’s also quite rewarding to watch locals light up when you ask them about their favorite places. There is a difference between the cheaper highs of novelty-seeking and frictionless convenience and the meaningful experiences that require us to step out of our comfort zones. In fact I would even say that meaningfulness is often directly proportional to the discomfort faced.

I’m much more interested in a meaningful personal experience in the current moment; Yes, the Renaissance was incredible, and yes, I’m super inspired by Da Vinci, but what was far more meaningful was the dinner we had the night before served in that small Enoteca by that short, quirky, and energetic Italian guy and his equally eccentric and stern (yet sweet) Italian-speaking German wife.

It’s important to honor and understand the history of a place (the Medici palace, David and Michelangelo), the parts of the whole that make it special, just as I’ve been thinking it’s important when I go camping to learn about the names of all the trees and plants, birds and animals.

10:08am

We went to an imitation “Da Vinci” museum on the touristy side of Florence. There were countless experiments and inventions there I’d never heard of or seen. The guy definitely had ADHD. He’s iconic now, for good reason, given his contributions to math and science. Truly passionately curious.

I think of this as I worry I worry about spending my time “efficiently” on the “right” things, not “too many” things.1. I want to write, draw, take photos, learn to surf, learn to play guitar, continue growing as a coder.

Curious, I looked up how Da Vinci supported himself during his lifetime and it turns out he was constantly debt-riddled, often distracted and fequently delaying and abandoning comissions and projects; but mostly supported himself through patronage. He was hired to do work across both art and engineering. Be more like Da Vinci! Make for yourself! Think of all his sketches. Just keep making things and (shamelessly) sharing them with others at all steps of the way.

9:54am

Things take on the character of when they’re constructed, and because they are shaped by constraints of time they were constructed they are forever intertwined with that character, the feeling of that time. The 1920s spanish-revival houses dotted across Los Angeles, the textured exposed brick buildings in Florence versus the modern generic “Anywhere, USA” aesthetic so prevalent these days. This character osmosis also applies to people.

September 7, 2026


4:18pm

Everything in this cute little corner store is right-sized. A small market of fresh foods, just a few of each grocery — not overstocked — just right; run by two hip, middle-aged Italian women. “It feels like you’re in someone’s kitchen.” I want to own a restaurant like this, a little nook in an alley (in old town Florence).

September 6, 2026


11:02am

We are drawn in by the facade of a quintessential cafe storefront window, we go inside and are greeted by a cavernous interior that unfolds to two stories, multiple sprawling seating areas, we hesitate and a couple locals who know the norms go ahead of us and find a seat (more assertively than us). I huff arrogantly, forgetting that I’m not center of the universe. It’s the morning rush on the weekend. All tables are taken, all manner of languages being spoken, the waitresses strategically cooling themselves off before hurrying to greet the next arrival. We get seated near the interior balcony; our perch gives us this unobstructed view of the goings-on below with the baristas and unassuming parties interacting, planning, ordering.

Maybe there’s a lesson in acceptance here, in being right on top of each other — in relinquishing control and embracing the (mostly) organized chaos. So much sound, but none of it noise, busy but not frantic; it’s not ear-drum rattling bass and I’m not interacting with chronically inconvenienced, underpaid (and therefore disinterested and disgruntled) servers. It’s something quite different than what I’m used to back home.

9:24am

Meagan and I made it a point on our one year anniversary to find a rose garden in Florence to read some renewed vows to each other.

I wish we had a million lifetimes together … it’s hard to accept that we’ll only have one, and it’s crazy to think it’s already been a whole year … here’s to fitting a million lifetimes of love into just one.

(In a way that I’m grateful for) I can’t shake this perspective of how fast time moves, of how bittersweet it is to have found a person you want to share everything with (every part of yourself, every experience) but then in these moments of clarity and perspective be struck by the realization that time moves very quickly in hindsight.

In the US, I feel so focused on moving forward, and so determined to shed the inconvenience of my past that I barely stop long enough to sit with the current moment; to actually, fully absorb that this day is the only thing I’ll ever have. Life is these steep Italian staircases, and these milestones are their landings; I’m slowly figuring out how to savor the struggle and take a beat when I get to each level, and in between breaths look out the window to enjoy the view.

September 5, 2026


8:00pm

Tiny street-level restaurant providing a frame to this new world. This hole-in-the-wall feels integrated into the night life. People are passing by in-and-out of frame. Life feels like it’s being lived.

It feels so nice to be out at night with no specific agenda, amongst others doing the same. Meals, restaurants are so much more social here. It stands in such stark contrast to the pervasive Western attitude of individualism and optimization. They’re all out on the sidewalks, they’re not only focused on themselves. This is as nourishing for the soul as this warm meal.

9:22am

Everything is smaller in Italy. Food portions, coffees, trash cans. They even treat garbage differently here. Us Americans consume so much.

Of the few things we do share with Italy, are the Mediterranean climate1. Dry summers and mild winters. Coming from sitting on a continent’s west side next to a cold ocean current and the corresponding drought-hardy evergreen scrub. Maybe the rainfall accounts for why it’s so much more of a rich, dark green here though. Fun new varieties of shapes and trees, especially the Italian cypresses and stone pines. The Tuscan landscape seems more cultivated compared to how untamed California is.

Also interesting to see what trends carry over from our culture (with the internet, social media): the orange-tinted glasses, American pop music on the radio.

9:18am

Everything moves at a slower pace here, at its own pace, there’s a lot more casual standing around. The police officers at the Florence airport are socializing amongst each other, one of them is playing tug-of-war with the drug dog. We step outside and everything else is a smaller scale too, the little billboards outside, the height of the buildings, the roadside signs. There is definitely more of a nonchalant attitude; I’m sure after a couple of weeks I’ll find out if that’s the pace here or just my novel read of it.