I usually use Wikipedia and guide books to pick specific places, guide books are usefully at libraries for free.

Then it depends on what you like, history/art? Do a search for historic areas, museums etc. Night-life? Search for exciting places or restaurants etc.

Over time I usually pick up, through reading, TV, social media, places I'd like to visit in a place and base my visit around what I already want to see.

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Thanks! I never used guide books or Wikipedia, but sounds an interesting idea.

I always scrape through the internet, and select interestingly sounding things to do and visit. I realised that visiting not unique things is nice, but I will quickly forget about them later.

I'm old and old school, I still will plan my travel on paper maps. Have fun planning and enjoy your trip.