The "web revolutionized the travel" industry, enabling "people to be their own travel agents". With the improvements in mapping technologies and the ability to share knowledge, it has never been easier to find the deals you need regarding the places you want to see.
Please list out the websites/web-apps you use most of the time.
Couchsurfing is a great way to find free places to stay, good people, and points of interest from locals. It requires an investment in the community, but if you are gonna do a lot of wandering it is a must.
I just tried using Atlas Obscura for a trip to Seattle and its the reason that we found our way to the freemont troll, which was awesome.