How Your Holidays Will Be a Success (Sort Of)

By IRMA, Someone Who’s Been There and Bought the Kaftan

Once upon a time, a holiday was something you just had. You packed a straw hat, a paperback, and vague intentions of doing nothing, somewhere vaguely Mediterranean. The only real decision was whether to tan before or after lunch. But somewhere between the invention of Instagram and the “limited-edition” beach towel collaboration between “Mega Brand X” and a Tuscan vineyard, it all got rather… curated.

Today, holidays require the logistical precision of a military operation and the budget of a minor royal wedding. You don’t go on holiday — you plan, optimize, and strategize your holiday. You are no longer a traveller; you are a brand manager for your own leisure.

Popular places are no longer popular — they are impossible. Hotels are booked a year in advance by people with spreadsheets and concierge apps. You wanted to swim in crystal waters? So did everyone else with a drone and a Pilates-toned waistline. And let’s not get started on the water itself — either it’s too clean (read: jellyfish fiesta), or it’s mysteriously brown due to climate something-or-other.

Remember when Capri felt glamorous because it simply was? When the South of France smelled like pine trees, not perfumed influencers? There was once a natural filter: people travelled with curiosity, taste, or at the very least, a reason. Perhaps they were penniless artists, quietly sketching the coastline while subsisting on wine and ennui. Or they were eccentrics with old money and older linen shirts, fluent in five languages and allergic to flashiness. Now everyone is a socialite — but none have anything to say beyond their sunblock SPF.

Still, assuming you’ve already booked something (you poor soul), let’s salvage what we can. Here are a few steps to ensure your holiday is — if not successful — at least bearable.

  1. Lower your expectations.
    This is the only true guarantee of happiness. If you go expecting the White Lotus, you will likely get white plastic loungers and a DJ named ‘Marco Sensation’ who plays until 4 a.m.
  1. Pack real books. Or a musical instrument.
    Reading a well-thumbed novel or softly strumming your guitar while surrounded by inflatable flamingos and Bluetooth speakers blaring Pitbull? That’s not just leisure — it’s a quiet act of rebellion.
  2. Just a little.
    Yes, your salad is photogenic. No, it doesn’t need to be immortalised. Try tasting it. Listen to the clink of glasses, the sea breeze, and not the TikTok next to you. Be there, not seen there.
  3. Seek out the forgotten corner.
    There’s always a side alley, a faded sign, a grandmother selling tomatoes from a crate older than your Airbnb account. That’s where your holiday begins — and where the WiFi often ends.
  4. Avoid trending outfits.
    You are not a campaign. You are not Resort ’25. You are on holiday. Let your skin breathe. Let your clothes have no hashtags. And let your kaftan do the talking (preferably in linen).
  5. Sidestep the trendy beach clubs.
    Ask yourself: do you really want to eat a €48 ceviche while a wannabe Go-Go dancer sprays Moët into your frutti di mare? If yes, congratulations — you’re not reading this.
  6. Choose your destination based on water quality, not capsule collaborations.
    That chic pop-up with the fashion x fragrance x furniture brand might look great on a tote bag, but it won’t help you when the sea smells like regret.
  7. Let your wardrobe fit your hotel, not fight it.
    If your sundress is louder than the lobby wallpaper, something’s gone terribly wrong. Choose a place where a simple white kaftan is as glamorous as it feels, not as it photographs.

Above all: seek the essence. Not the WiFi. Not the restaurant that’s trending. Rather the authenticity. It might just be hiding behind a half-closed shutter, down a cobblestoned alley, where no one has updated the interior since 1963 — and thank god for that. (You should read our article about Albergo Quattro Fontane. HERE)

Because true holiday success isn’t in the reservation. It’s in the moment you forget what day it is.