Container Bar, you just keep getting better!
First, the cool factor: It's a bar in an alley! Checkmark. But they also do food and drinks right here. For summer sipping, you can't beat one of their slushie cocktails in my opinion. Or go full bore and just get the pina colada out of a coconut (topped with a skewer of fruit and served with a spoon to scrape out that coconut, should you want to make your $17 drink into a meal).
I was a little cool on their food offerings (a lot of it is cooked in duck fat and I'm not a meat-eater) but this summer they added several duckless $5 appetizers that fill the void when we're just out for drinks (like the spiced popcorn or weird but entertaining boiled peanuts). There are salads and a veg burger on the menu too for the vegetarians and pescetarians in the crowd looking for a meal.
I like Container Bar for entertaining friends from out of town or just out of the neighbourhood. It's good when it's one of those too-hot days and you need some shade and a grownup slurpee (it's shaded 99% of the time at Container Bar). And when summer stretches into cool fall nights, they'll hook you up blankets and switch on the heaters so you can keep on cocktailing.