I don't practice alot of street photography or travel portraits, as a percentage of my total body of work, but I've done my fair share of both. At first, the genre intimidated and frustrated me but I've found some tips and workarounds I'd like to share that will hopefully make you a better travel or street photographer on your next trip. Here are a few random thoughts:
Approaching strangers on the street for photos used to intimidate me until I changed my attitude. Instead of feeling intimidated (seriously, what was there to be "intimidated" about?) about approaching people because I assumed they didn't want to be bothered, I starting assuming they DID want to be photographed. Most people would be incredibly flattered to be asked by a professional photographer to have the photo taken. Wouldn't you? Once my attitude changed, that became so much easier.
Walking around looking for interesting moments to happen is difficult. In addition to being an extremely good observer, your reaction time has to be precise - or the moment is gone in an instant. Instead, I sometimes find a scene I really like with good strong composition, set the camera on a tripod and then wait for someone to walk into the scene. Then click.
Wear boring, drab clothing. Blend into the scenery. Don't stand out.
4. For portraits, don't take out your camera right away. Invest some time in the encounter by having a converstion with the person. Ask about his or her job, family, home town, favorite or local foods, etc. Once you've established a rapport and certain comfort level, ask if you can take a photo or two. I've hardly ever been denied and the results are much better with a relaxed subject who happens to trust you.
Be a gear minimalist. Take one body, one lens, and maybe a tripod. Maybe. I've found a camera backpack filled with lenses and gadgets only get in the way - both physically and my ability to observe and focus.
I, too, am involved in portrait photography as well as many other genres of the medium. I have met fascinating people by approaching them and photographing them. I have made many good friends by interacting with them taking their photograph. I think the idea is to remain neutral when you present yourself to folks that you don’t know Start a conversation and see where it leads to. Interacting with strangers, taking their photographs is much easier today than before digital imaging came to be. My workflow with strangers is to make an opening photograph show them the LCD screen to get them involved with the process as a way of Breaking the ice and having something in common to collaborate on. I have found that collaborating when shooting portrait is the key ingredient in capturing an insight into what is not on the visual surface.