1) What is the local food specialty?
2) Is there a free walking tour?
3) Which top tourist attractions are must-see's?
4) What should I drink?
Sure, you can always order a craft beer or glass of wine from a nearby vineyard (which I definitely like to do), but there is often a lot more to local beverages than what may initially come to mind. From Turkish coffee to Moroccan tea; Valencia's horchata to Switzerland's Rivella, there are drinks hot and cold, sweet and refreshing that are unique and deserve to be tasted... be sure to ask your waiter / bartender / taxi driver!
5) What is culturally relevant?
Aside from local sports, music and art are among my favorite cultural things to explore when traveling to a new place. I've been to the opera in Vienna and a traditional music 'session' in Ireland. I've even been to a rock concert in Buenos Aires to see a great band that never made it to the US charts. Taking a look at event calendars on city websites or in free magazines found in many shops and restaurants are great resources for finding out what is going on while you are in town.