How to Plan a Holiday like a Pro

Or rather, like a perfectionist.

Oh holidays! Those hazy dreamy weeks where you lose track of what day it is, drink wine at lunch and start asking yourself questions like “how long would it take to be fluent in Portuguese?” and “how many gelatos in a day is too many?” After two years or more of closed borders and 24hr testing rules and lockdowns, we’re all craving a little escape!

While the holidays themselves can be glorious idylls, actually planning a holiday is both an art and a science. Like a wedding or a birthday party or anything that’s big and weighted with emotion, you’re trying to translate all these nebulous daydreams and feelings and hopes into something tangible and real. Something with structure and length and flow and (sadly) a price tag attached. Now, as a Taurus, I LIVE for this shit. I will create a google doc and a spreadsheet and a map so detailed your head will spin. I will hunt down a hotel or a restaurant I saw referenced in a strangers instagram story 5 months ago. I will check and cross check room availability and prices and present you with three different options based on budget brackets and transport connections. All the research and the planning makes me positively GIDDY.

I realise that to some people I will sound insane and all that work sounds like absolute hell. If you’re the kind of traveller who likes to book a plane ticket and a hotel room for their first few nights and then wing it - honestly I salute and fear you! - this guide is probably not for you. For everyone else, let’s go!