Planning and more specifically, creating a day planning for your city trips, sounds exactly the opposite of the omakase way of doing things. You can read my separate post on why this is not the case and how I plan to help me experience more – sometimes is a planning a necessary evil, sometimes it radically improves your travel experience. But even when I am planning, I try to apply omakase-thinking 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, here’s how I create a day planning for my city trips.

1) Lock in the set variables

If you’ve read one of my planning and preparation posts (for example for my Jordan Trail hike or for my GR20 hike), you’ve probably noticed, I like to lock in the set variables as soon as possible. Are there any events I need to attend (conferences/meetings)? Are there other things I need to do? When am I traveling to/from the destination and how does that impact my travel schedule? Do I need a specific hotel because of early flights? Are there special days (bank holidays, special events) I should take into consideration, etcetera.

This helps me to assess the need to a day planning for my city trip.

2) Assess the need to a day planning for my city trips

To what extent I want to plan my trips differs from city trip to city trip, also based on the set variables (see above). E.g. when I went to Japan (Kyoto, Osaka, Tokyo) I had a rather detailed planning because I wanted to maximize my food experience (go to as many good restaurants as possible) and did not want to waste a lot of time in a huge city like Tokyo crisscrossing town. When I went to Madrid with my wife, we did not plan at all and just explored some roughly indicated areas of the city.

In general – the bigger the city and the more tourists, the more likely I am to spend time making a rough day planning to avoid crisscrossing the city and to avoid huge gatherings of tourists. The bigger the city, the more likely there is a vibrant food community and there is a need to plan your restaurants beforehand.

3) Planning preferences

I have some personal preferences when it comes to planning my city trips.

  • I like to travel early in the morning. I hate flying late in the evening or even late in the afternoon. Especially the last day of my city trip I hate lingering around town waiting for the moment to leave for the airport. When flying in, I always find it a waste of a hotel night to fly in late to only be able to visit the city the next morning.
  • I like to spend the night close to where I have to be. Most of the time, I will try and get a hotel close to the city center (or a public transport connection that will bring me to the city center really fast), rather than spending the night outside of the city and traveling in.
  • I’m a points guy. I will usually look for hotels that are in the loyalty programs I spend the most time in (Hilton and IHG).

4) Rough planning

Depending on the need to plan, I will write down a rough planning for parts of the day:

  • Sometimes: pre-Breakfast. I am an early riser (I usually get up between 4 and 6 in the morning), so I quite regularly will go for an early run, a hike through the city or an early visit to places I’d like to visit.
  • Breakfast: Breakfast and I will probably never be best friends (not my favorite meal of the day), so I’ll usually eat breakfast in my hotel or on the go.
  • Morning: I tend to pick one or two areas of the city I’d like to explore for each part of the day.
  • Lunch: Especially in cities with a vibrant food culture, I will tend to have a rough idea where I want to have lunch. I will often go to the fancy places (e.g. The Jane in Antwerp or Fismuler in Madrid) for lunch – often lunch is cheaper, more likely to be available (often, evenings are fully booked) and I don’t like the feeling of a food coma late at night.
  • Afternoon: I tend to pick one or two areas of the city I’d like to explore for each part of the day.
  • Dinner: Especially in cities with a vibrant food culture, I will tend to have a rough idea where I want to have dinner. As I often pick the fancy places for lunch, dinner can be anything – from a great ramen place to a more fancy place.
  • Evening: I tend to pick places that have a specific extra value for the evening – e.g. places with great light, that are romantic, that are only open at night, etc.
  • Night – I tend to spend my nights in either Hilton or IHG properties (although I have been starting to explore more Marriott properties recently)

So, what is your way to plan for city trips?

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