The Correct “Plan : Wing It” Ratio


As a serial planner by nature, I write this more as a story of conversion than anything. Let me start by saying there is NOTHING wrong with planning your trip. It’s great to have focus, a pool of sights to see, knowledge of transportation and lay of the land, etc. But a schedule with time intervals allocated to each location is where I (now) draw the line. I used to take pride in the ability to have every detail mapped out to a T. I did this for YEARS until one trip to New York I found myself passing up on a karaoke night in SoHo because my evening was booked solid with things I had pre-planned to do. I didn’t think much of it at the time and honestly at this point there is really no sense in speculating alternative outcomes. However, what I did take away is that although you do everything you want on your list, having a schedule booked solid forces you to miss out on spontaneity – something that could have been the adventure of a lifetime.

So how much planning is enough?

When O and I decide we’re going somewhere, it’s usually about a week to 48 hours before departure time so elaborate planning is without a doubt out the window and only the bare essentials are on the table. He’s in charge of coordinating flights and I check the weather and culture of the location. This includes things like checking the state of WiFi in Havana before planning to google things upon arrival.

First things you search after choosing a destination are official language, currency and weather – will you be able to communicate, can you afford it and is it nicer than the place you are trying to escape? Seems straightforward.

Then I do a quick sweep of main attractions and rate their value to my trip. I.e. when deciding on a trip to Florida, the beaches and nightlife of Miami will have a greater pull for a 20-something single traveler than Orlando with its family vibes and pictures with Mickey.

Next is your geography lesson. What are the neighboring cities/towns and are you down for day trips? What are some major streets of your destination? This will help immensely when deciding where to book a place to stay and calculating its proximity to the sights of interests.

Finally your food, drink and ride. What is the local food and are there familiar alternatives? Where do people go for drinks with a view or without breaking the bank? Is there public transportation or is it worth it (or possible) to Uber?

After this, everything else will fall into place. Leave your trip wide open for recommendations from locals and unexpected plans that will come your way. Trust me, it will be better than anything you could have planned ahead.