I'll start: I am a Product Manager working in NYC
I usually have a list of places I want to check out, like Iceland, New Zealand. I also periodically look on Travelzoo for any vacation packages.
After I know where to go - I book my flights on Kayak and
Then I go and research the web/google/TripAdvisor etc to find out what to do when I get there. Like what cities, what points of interest, what restaurants etc.
I copy and paste the information in a spreadsheet or a document including addresses and any other information.
Then comes the painstaking part.
I then decide what to do on Day 1, Day 2, Day 3 etc by looking at proximity of these places in Google Maps and duration of these activities and then create a tentative daily schedule.
I then book my hotels on hotels.com or booking.com. Not too much into Airbnb unless I am going with a group of people.
Then I put this document on a Google Drive or print it out so I can consume this info while I am on my trip.
Wondering if other people put in the same effort and what their workflow is.