San Telmo has more of an old world vibe than I feel in other areas of the city. The buildings are generally older and there are really no high rise apartment blocks here. Food shopping is mostly smaller markets as there is no big chain in San Telmo. It is not that far to one of the chains....and they deliver. There is an English book exchange/store on United States a few blocks off the plaza. There a bunch of places to eat on Chili and Defensa and also all around the Plaza Durego. Otherwise they are scattered throughout. During the week days you can sit outside and eat and watch dancing (tango and other styles) right in the plaza. Also, there are a few good tango clubs right off the square. It gets really crazy on Sunday with the market. I am female and have lived in San Telmo for about 7 months and have never had a single problem with safety. Pickpockets are a problem on the subte (metro) so watch your bags. Have not heard of anyone having a problem with crime other than that. As with anywhere, watch your stuff and grab a taxi home if it is late. (the subway stops running at about 10pm) I would stay on the Plaza Durego side of San Juan. Also, make sure you have air and heat as the older buildings do not necessarily have those perks. As far as Spanish, I have found that very few people (once you get off the Plaza) speak English. My speaking was quite dodgy when I got here and the people are quite friendly about helping you out and figuring out what you need. Plus, it makes you learn!! If you have any more specific questions feel free to ask.