Before you go out and shoot, you must decide where to go out and shoot. I usually go to an area with lots of people walking around. Museums, parks, or any downtown area work very well. The more people you have in a certain area, the more likely your chance of finding interesting subjects to shoot.
However you shouldn’t only limit yourself to heavily-populated areas. The beauty of street photography is that it has no limits. You can shoot photos anywhere; it doesn’t only have to pertain to the streets. You can probably find great subjects for photographs in very mundane places like the grocery market or even the library. The entire world is up for grabs.
Above all, the best way to go out and shoot is to pick a location and simply go out. Have a few places that you want to check out in mind, and let your curiosity guide the rest of your little mini-journeys. When I go out, I prefer to take an entire day walking around while taking public transportation to get to my location, be it the subway, bus, etc.
I also bring all of my stuff in a messenger bag, as it makes taking things easily accessible. I typically only carry around 2 prime lenses (my Canon 35mm f/2 and Canon 24mm f/2.8) along with some water and some food. Also just in case, I make sure to pack an extra battery and memory card along with any other random necessities I may need. However I try to always keep my bag as light as I can. Just for reference, I use the Timbuk2 Commute 2.0 bag which I highly recommend that holds nearly all of my stuff. Although it is a bit pricy, it is made out of fantastic materials and also has room to carry my laptop as well. Messenger bags don’t have to be expensive, however. There is a great deal for several in different colors on Amazon for under $20.
Once you walk, bus, or metro to your destination, just feel free to walk wherever you want. Lead yourself down barren alleys, into random stores, and toward strangers. Open up and talk to the local people in the area and strike up a conversation. Tell them about your photo journey and if they have any places that they recommend you check out. Don’t be too picky with what photos you decide to take. If something just attracts your eye for one reason or another, take a photo of it. Don’t feel obliged to only take photos of what you would consider “street photography.” Keep your mind and options open.
After a long day of shooting, go home, download your photos from your memory card to your computer, and have the fun of picking your best images, while reliving your exciting little adventure.