Whenever we board our flight to our holiday destination I look around and see other travelers fiercely clutching their Lonely Planet guide books to countries X & Y. I then have a moment of panic like "crap. I should have bought one of those, too" but then I realize that I love how we approach it. We aren't big on planning what to do and see when we arrive to our destination since maps don't make much sense until you're actually there anyway and we often go off of the day's weather and how late we stayed up the night before. Of course we pre-book our lodging in neighborhoods that we research for their ease of transport and available services but other than that, we figure that we'll see the major points of interest along the way and find our own little gems by happy surprise (ie. this rad little bar literally tucked inside of an alley).
However, for as much information that I don't collect before we depart, upon arrival you can bet that I'm the first person at the info kiosk loading up on every free brochure, map, and local magazine available. Those are my golden tickets to a city. Particularly the local independent weeklys that often feature ads and reviews for great cafes and shops, which often lead to great little neighborhoods. I was getting my fill of these in Melbourne when I found an Urban Walkabout for Melbourne City. It was a non-planner's dream because it suggested shops, galleries, restaurants, and bars all over the CBD that we could wander to and explore with a bit of local knowledge. Then I found more for other creative neighborhoods and I was hooked. The design, the layout, the simple and approachable information - these guys know what they're doing! In Sydney I found their "Style Seekers" publication (also free) and was even more impressed. They have curated itineraries from local artists and business owners and offer all of the basic information you need to feel the creative pulse of the city. At that point I finally downloaded their free App and, you guessed it, was really impressed.
I did cheat on Urban Walkabout a bit with Broadsheet and Time Out but there's plenty of local info to go around, right?
What kind of traveler are you? Do you plan everything you want to see and do or do you go with the flow?