Why I create a day planning for city trips

This blog is called omakase and is about the art of leaving your expectations at home. The Japanese habit of omakase (お任せ) when you’re ordering at a restaurant pretty much means, “I’ll leave it up to you”, inviting the chef to be innovative and surprising in the selection of dishes. I try to do it in every city I visit and apply the idea behind to everything between how I pick my runshow I pick my foodhow I plan activities with my kidshow I explore cities and how I travel in general. So planning and more specifically, creating a day planning for your city trips, sounds exactly the opposite of the omakase way of doing things. So, here are some thoughts on how planning actually helps to maximize for omakase experiences – why I create a day planning for city trips.

To be completely frank, most of the time I do not make a day planning when visiting a city. I just go with the flow, soak in the city. The recent city trip to Madrid I did with my wife Marieke is a good example. But in some cases, like with my visits to huge cities like New York and Tokyo, I will create some sort of rough day planning – day planning for city trips.

Some things can’t be done without a plan

Laugavegur trail in the snow
Laugavegur trail in the snow

Some things are just really hard to get done without some sort of a plan. Running a marathon, hiking through snow, hiking through the desert, having dinner at a fancy restaurant like The Jane in Antwerp. So, planning, in some cases, is just a necessary evil to get things done.

Planning often helps you avoid common mistakes

New York Uber ride
New York Uber ride

The first time I went to New York, I would find myself crossing Manhattan North to South, South to West, spending countless hours walking through different Avenues and in the Subway getting to the places I wanted to visit. It was a complete waste of time. Better would have been to visit specific parts of the city on specific days – e.g. just visiting Williamsburg on one day, spend some time there or just heading over to Lower Manhattan and spend the day there, rather than rushing from Lower Manhattan to the Meatpacking district to Times Square to Williamsburg and back. Some sort of planning will avoid you crisscrossing the city.

In Kyoto, I really wanted to visit the famous Fushimi Inari-taisha, the iconic orange gates. But, as I quickly learned, by far the best moment to visit the shrine is early in the morning, before busses of other tourists flood the mountain and make visiting the shrine more of a procession than it is a magical experience. Some sort of day planning for city trips will help you avoid suboptimal experiences.

Planning gives some sort of direction for omakase experiences

In Malasana in Madrid
In Malasana in Madrid

Especially with larger cities, activities tend to cluster in specific areas of town. Williamsburg in New York, De Pijp in Amsterdam, Malasana in Madrid, etcetera. Specific areas of town where you will find vintage places, younger/hipster audiences, etc. Knowing this and planning for this, help increase the change you will have omakase experiences. It’s just way easier to have a good time in a residential area than in a business area, it’s easier to have some amazing food in a multi-cultural area than in a sleepy suburb, etc. Some sort of day planning for city trips helps you give some direction for omakase experiences.

Planning helps you to let go

Having some sort of plan often helps to let go. When you have prepared elements of your trip before heading out, you don’t have to think about it when you’re enjoying your trip. I realized when traveling to Hong Kong some years ago, that I would spend a lot of time talking to locals and finding things to do in town. So I would be wasting a lot of time just getting around town. Some sort of day planning for city trips will help you focus on doing rather than thinking.

Additionally, not worrying about places to stay, how to get to the city center, where to store your luggage, etcetera, will often give you the peace of mind needed to but fully open for new experiences.

Without a plan often no execution

I have noticed through my trips that having some sort of a plan will help you to execute. It is convenient to stay in bed all morning and see what happens, but getting up early, do a run, get in contact with locals who are up early as well is a great start – you’ll have the feeling you do more and will actually do more. A day planning for city trips helps to execute.

So, how do you balance planning versus enjoying in-the-moment experiences? How do you maximize omakase through day planning for city trips?

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