I spent a month between Spain, Italy, and Greece—here's one travel rule I’d break next time

I used to travel like a kid let loose in a candy shop with a stopwatch — counting cities, tasting everything once, sprinting to the next shiny thing. My most sacred rule was simple: never go back to the same place twice.

New, new, new.

Then I spent a month ping-ponging between Spain, Italy, and Greece, and the moments that stuck weren’t the “ones.” They were the seconds — the repeats.

In Madrid, a narrow bar in La Latina pulled me in during la hora del vermut, that pre-lunch window when the city exhales and clinks glasses. I ordered awkwardly, got a small ocean of olives, and watched three generations argue lovingly about soccer. It felt like a perfect accident. By my rule, I should’ve left it in amber and moved on.

The next afternoon, I walked past, thought about the barman’s wrist-flick topping the vermouth with seltzer, and broke character. I went back. He recognized me and slid over a wedge of Spanish tortilla I hadn’t asked for. Warm middle, glossy olive-oil sheen, onions sweet enough to make you forget your last three disappointments.

The second visit tasted like recognition — and made sense of why vermouth culture in Madrid has roared back to life. (Curious? Start here for a primer on vermouth hour and here for where to drink vermouth in Madrid.) 

Barcelona tested me next.

There’s a café in Gràcia with wobbly tables and a terrace that wears the exact slice of morning sun you’d want as a scarf.

First cappuccino: good.

Second: a conversation about why their oat milk foams better if it rests, plus a tip on a bakery two streets over.

Third: the barista waved me inside to smell a fresh bag of beans, and I swear the room shifted from “pretty neighborhood” to a map of small rituals.

Repeats turn a city from postcard to practice. (If you don’t know Gràcia, a local’s guide captures the village-inside-a-city vibe.)

Rome tempted me in Testaccio.

I found a trattoria where the carbonara arrived glossy and alive, the guanciale crisped to the point of ritual. My inner tourist whispered, “There are a thousand trattorie. Keep moving.” My stomach replied, “No.” I returned two nights later and got puntarelle I hadn’t seen on the menu — curly chicory shoots in an anchovy-garlic emulsion decisive enough to straighten your posture.

The server learned I like my espresso ristretto-ristretto. I learned Testaccio isn’t just a neighborhood, it’s a food language. 

On Naxos, I found a taverna tucked from the harbor where the printed menu is a prologue and the real story sits on a silver tray: what the farm sent that morning.

First meal: grilled eggplant with unjustifiable amounts of garlic and a bowl of golden fava wearing capers like confetti. I paid, strolled the marina, caught a thyme-and-sea-salt gust, and boomeranged right back. The owner waved like we’d rehearsed it. “You try,” she said, setting down zucchini blossoms stuffed with rice and mint—nowhere on the menu. We talked about sigá-sigá—“slowly, slowly”—and she laughed at my accent, a Spanish speaker trying on Greek vowels. I wore the joke like a badge.

Somewhere between those seconds, I understood what my rule had been stealing. The “no repeats” mindset gives you breadth, sure, but it quietly subtracts depth.

Day one, the pintxo tastes like the bar; day two, the bar tastes like your relationship with the person who plated it. Day one, a piazza is a backdrop; day two, you know which bench dodges the noon sun and which pigeon is the diva.

Repeating isn’t laziness — it’s a lens.

It changed how I packed.

Repeats meant fewer clothes and more rituals—leaving a sweater on the back of a familiar chair, knowing I’d see it tomorrow. It changed how I planned—blank mornings to loop back and watch a market shift from clatter to hush. It even changed how I took photos. The second visit made me patient enough to wait for the light to creep three feet across a tile wall.

The counterargument writes itself: if you don’t repeat, you try more. True. But choosing one place to return to didn’t shrink the trip; it deepened it. It was like picking a favorite track on an album. You can still hear the rest, but the favorite teaches you how to listen.

Back in Madrid on my last night, I went for an encore. Same tiled bar. Same barman. He glanced up and lifted the bottle before I opened my mouth. “¿Hoy, mejor?” Today, better? The olives were saltier, the vermút colder, the room somehow warmer.

Nothing had changed except me, and that was the point.

Next time, I’ll bake in a single rebellion per city. One repeat on purpose. One cappuccino sequel. One trattoria do-over. One taverna encore.

Because novelty is a great way to arrive — but repetition is how you belong. And if you need a nudge, let the city’s own vocabulary remind you: Madrid’s vermouth hour, Rome’s puntarelle, Greece’s sigá-sigá. All of them say the same thing in different accents — slow down, come back, taste again.