How To Travel To A City

I don’t travel much and I am bad at traveling. This is a guide for a very common type of trip: traveling to a city.

Overall

take the time to prepare and explore! That’s the only way to maximize and make good use of your time
always book an extra day after arriving home to decompress after the trip
travel during unpopular times of the year, week, day
take so many notes! Write down everything you did, any observations, differences, etc.

read through the location’s subreddit
watch travel TV shows that take place in the area
- No Reservations
- Parts Unknown
- Travel Man
- Reluctant Traveler
watch some movies or TV shows that take place there
check travel publications
- Monocle
- Lonely Planet
find some itineraries from travel bloggers
- Rick Steves
find a book that takes place in that location and read it ahead of time
make a playlist of music that will fit the trip vibe
learn as much of the local language as possible, this pays off huge
visit Atlas Obscura

plan ~1 “anchor” activity for every day (travel, museum, hike, etc.)
put all interesting items on a map that can be checked day-of, or at any point when plans change
aggressively check holidays, opening hours, seasonal closures, etc.
spend at least 3 days in every city

A few notes on packing for city travel:

avoid packing clothes specific for travel days. Instead, have clothes that are comfy enough for travel days and normal days
pack versatile items that make sense in multiple contexts (Birks, bomber jackets, tech pants)
pack for layering, which includes layers that make the outfit warmer/cooler and fancier/casualer
if there are any odd activities coming up (e.g., hot air balloon ride) make sure to pack for those
don’t pack aspirationally for things that might come up, they almost never do
it’s more important to pack light than perfect. Bring a smaller notebook, less cash, light water bottle
be generous with toiletries (or accurate, if possible)
it’s a huge benefit to spend at least some time at an Airbnb with a laundry machine, or somewhere with many laundromats since this cuts packing volume almost by half
leave some empty luggage room for gifts on the way back

There will be travel to, from and at the destination! Probably by different modes (plane, train, car, etc.) It pays to be prepared.

the best time to arrive somewhere is about 6pm. It’s after rush hour, and it’s just enough time to get into the city, have dinner, go out for a drink, and then crash
carry a water bottle and snacks
bring entertainment. Movies are the most distracting, but games, books, and podcasts are also really good
wear a mask (at least to the destination), getting sick will completely ruin a trip
an e-reader is better on a plane since it provides its own backlight
check the airplane seat map before booking to figure out which seats are decent

Almost all cities are kind of the same, especially in North America. Seek out the differences!

Otherwise, do as the locals do?

what does the city have access to that’s fun to do? Are there lots of museums? A strong food culture? Beautiful buildings?
is there anything going on in the city at the time? Maybe a festival, or a sports event, or seasonal change
are there any concerts on? How about local movies?
what kind of food is popular here, and what restaurants do it right?
is there someone who lives there to get a meal with?
is there a high vantage point from which to look at the city?
book a walking (or bus, or bike) tour of the city, on an earlier day
read a simple book in the local language

usually, short work trips are about meeting people and doing things. Don’t bother bringing computer gear
you won’t have that much free time alone, the whole point is spending time with others
when traveling west, sleep later, and stay on your original schedule
when traveling east, don’t sleep on the plane and let yourself be tired to match the original schedule
9/10 times you won’t be able to fit your carry-on rolly without upgrading your seat, and it’s hard even then