The Myth of the Perfect Season (And Why You Should Stop Listening to It)

There’s a particular smugness that creeps into travel advice the moment anyone utters the phrase “best time to visit.”

It’s in every guidebook, every glossy magazine article, every influencer caption dripping with lavender fields and sun-warmed lemons: “Avoid the crowds by visiting in shoulder season!” “The best time to go is just before peak season—when the weather is perfect, but the tourists haven’t arrived yet.” “Don’t even think about going in summer, it’s far too hot.”

Oh, how exhausting.

This cult of the Perfect Season has become so widespread, so deeply internalized, that many people now believe it’s irresponsible to travel at the “wrong” time. Heaven forbid you enjoy yourself in August. Heaven forbid you walk through Venice in January.

But here’s the truth that no one likes to admit—certainly not the magazines, and certainly not the people who’ve pinned their entire self-worth to having “done Tuscany properly”:

The best time to visit anywhere isn’t always the time you’re told.

And sometimes, the “wrong” season is exactly when the magic happens.

The Cities That Bloom in “Bad” Weather

Let’s start with Venice. I’ve been in the textbook “right” months—May, September, that narrow window in October before the mist settles and the canals start to chill.

Lovely? Sure. Predictable? Absolutely.

But the best time I’ve ever been to Venice? January.

Dead of winter. The city all but emptied out. The fog curling through the alleyways like cigarette smoke. Everything damp and shadowed and smelling faintly of old wood and saltwater. No lines, no crowds, no sweaty day-trippers cramming into the vaporetto. Just me, a coat that was slightly too thin for the weather, and a city that felt like it had folded itself inwards for its winter nap.

Was it cold? Of course it was. Did I care? Not even slightly.

Or take Siena in September. Everyone tells you to visit Tuscany in spring, when the poppies are out and the hills glow that impossibly lush shade of green. But September? That’s when the city exudes this languid, honeyed mood—summer’s last gasp, golden light bouncing off the stone piazzas, locals slipping back into their routines after the August holidays. The air feels heavy with wine and dust, but in the most seductive way. You can sit in the square until midnight, long after the day-trippers have disappeared, and it feels like the entire city belongs to you.

And then there’s Essaouira in February. Windy, yes. Brisk? Sometimes. But also—utterly, disarmingly beautiful. The Atlantic crashing against the stone ramparts, the streets quiet enough to wander without dodging crowds, and that delicious sense of otherworldliness that Morocco always seems to deliver best when it’s not trying to impress anyone. It was perfect precisely because it wasn’t the “right” season. No performative magic. Just the real thing.

Why the “Best Time” Obsession Ruins Good Trips

The problem with the Best Time to Visit myth isn’t just that it’s wrong. It’s that it lures people into a false sense of control.

People think that if they hit that ideal window—the precise two weeks when the weather is temperate, the crowds are thin, and the prices haven’t yet soared—they’ll somehow unlock the ultimate version of a place. As if a destination is a video game level, waiting to be completed with the right cheat codes.

But most of the time, what actually happens is this:

They arrive during “best season” along with everyone else who read the same article.

They find the streets thronged with people clutching the same guidebook pages.

They book the “hidden gem” restaurant that now has three sittings a night and an English-language menu.

And then they come home saying, “It was nice, but a bit touristy.”

As if they weren’t part of the crowd themselves.

The reality is, you can’t manufacture magic with a calendar. The best trips aren’t about weather reports or shoulder-season discounts. They’re about how you show up—and whether the place meets you halfway.

The Trade-offs Nobody Tells You About

Now, I’m not suggesting that every destination works in every season. Some places are deeply, unapologetically seasonal—and they require a little strategy.

Florence at Easter, for instance? Absolutely worth it. The city practically glows. The festivals, the sense of renewal in the air, the streets humming with both locals and visitors in their best clothes—it’s theatrical in the best way.

Scotland in October? Heaven. That low amber sun slicing across the hills, the moody landscapes turning everything into a gothic novel, the smell of peat fires curling through the villages—it’s cinematic. You will feel like the protagonist in some windswept period drama.

But I’ve also had wildly unexpected joys in seasons that “shouldn’t” have worked.

Edinburgh in August, during the Fringe? Absolute chaos. You will not find a quiet moment. You will, however, find yourself tumbling between pop-up shows and late-night bars, meeting strangers who feel like old friends by dawn. It’s not the brooding, misty Scotland everyone romanticizes—but it’s electric in its own way.

Athens in March? Shockingly beautiful. Bright, clear days. Temperatures perfect for wandering without wilting. Enough tourists to keep the restaurants lively, but not so many that you need to elbow your way to the Acropolis.

Even the south of France in the height of summer—which everyone loves to write off as “too crowded, too hot, too obvious”—has its own charms. Yes, it’s sweltering. Yes, you’ll want to be horizontal between 1 p.m. and 5 p.m. But if you’ve secured yourself a shaded villa with a private pool? A fridge stocked with rosé? Frankly, who cares about the lavender fields. You’ll be exactly where you’re meant to be.

The Beauty of the Wrong Time

Here’s what nobody tells you when they drone on about “best time to visit” lists:

Sometimes the trip is better because you went at the wrong time.

Because you weren’t chasing the picture-perfect version everyone else was chasing. Because you stumbled onto something quieter, stranger, or more personal. Because you gave yourself permission to stop listening to the crowd. Some of my favorite travel memories didn’t happen under postcard skies or in “ideal” conditions. They happened in unexpected, slightly off-kilter moments: the kinds of trips that no algorithm would ever recommend.

Travel isn’t a performance. You’re allowed to go somewhere when it doesn’t make sense on paper. You’re allowed to love a place during its awkward season. You’re allowed to enjoy yourself in ways that don’t photograph well - or worse, won’t impress anyone at the dinner table.

But.

The One Exception

Sometimes, we do find that clichés exist for a reason.

Italy in July or August? No. Absolutely not. I will die on this hill.

The heat alone is biblical: thick, suffocating, and relentless, like walking through hot soup while dragging a suitcase with one busted wheel. From Milan all the way down to Naples, it’s a wall of heat that doesn’t let up. And then there are the crowds. Throngs of schoolchildren on language tours, sunburned tourists in matching linen sets, swarms of cruise ship day trippers clutching melting gelato and blocking every scenic viewpoint.

It’s Dante’s Inferno in zip - off cargo shorts.

Even the Italians know better. The ones who can afford it? They flee—to the mountains, to the coast, anywhere but the cities. The shops shutter, the trattorias close, the streets are left to roast in the midday sun.

There is no hidden pocket of charm. No secret square to redeem it. You will be hot, you will be miserable, and you will hate yourself for ignoring this warning.

Unless, of course, you’ve already secured a shaded villa on the coast—somewhere with a private pool, sea breezes, and enough staff to keep you supplied with icy Negronis until sundown. If that’s the case, well… you already know how this works.

But for everyone else? No. Absolutely not. Save yourself the torment.

Italy's summer hellscape aside, the “perfect season” is a myth. Always has been.

Go when you want. Go when you can. Go when it feels right, even if the guidebooks wag their fingers at you. Ring me first, if you have a truly feral idea.

The weather will pass. The crowds will come and go.

But the stories you bring home? Those are yours - untidy, unseasonal, unforgettable- no matter when you went.