Unless you have kids, avoid Sentosa. The botanic gardens are nice, especially for morning/evening jogging. The orchid gardens inside are especially gorgeous. Orchard road is technically touristy but good mix of locals there. For some serious culture-hopping, check out Arab St and Chinatown.. I think Bugis Junction is a lot more interesting than Orchard. Oh yea, and.. ALL tourist malls are the same!
Food is excellent everywhere, including at the airport.
