Trip to NYC and LA (off-the-wall ideas)?

Well, how far are you willing to travel outside of New York and LA? There are definitely things to do if you are willing to travel. If you're not, and you want to do something with drinking, I'd check out Brooklyn Brewery, Kings County Distilleries and New York Distillery Company. IF you're willing to travel a bit, there are some great options out on Long Island and across the river in Jersey. If you want to do off the beaten path, just start walking and find places that look interesting - Manhattan is full of them. Since you'll be here in June, I'd recommend catching a Mets or Yankees game as well. Other than that, it's hard to give advice without knowing what exactly you're looking for.

In terms of NYC: Mercury Lounge, Hard Rock Café, and Times Square--yes Times Square is filled with tourists, but if you look more in the fringes you can find other less visited places.Also look in the flat-iron district--some pretty unique stuff there too. And you might want to do the Wallstreet tour as well--it takes you through the exchanges and a whole lot of the area down there. Oh yeah, and do the boat tours too--the tour just takes you around the Island of Manhattan, but its supposed to be really good for pictures. And I almost forgot, take a Ferry--anywhere, just take one. That's also another good picture setting if you're into that at all, plus the Statue of Liberty/Ellis island route is really good. Personal recommendation--if you're into history at all go to Ellis, spend a whole day there but forget about the statue. In terms of historical stuff Ellis is really a unique experience and not as popular while absolutely everyone feels obligated to go to the statue when in my opinion its not that good or interesting an experience up close. Also, if you do want to go to the statue at all (I know you said you want off the beaten path but I'd figured I'd throw this in there in case you decide to do at least one tourist-typical thing), get to the Sea Port at like, 5 or so. Seriously--or else it won't be worth it--they give a selective number of tickets at around that time to see the whole thing, otherwise you get limited to like, the first 2 floors or something. Oh yeah and Sea Port is another pretty unique area--I'm sure you'll be able to find some pretty good places down there too in terms of food and/or drinking that aren't hit as much by tourists.

Trump tower.

Also take a good hard look at the crazy protesters just across the street

Venice Beach brah

In LA, Santa Monica and Venice are the best "drinking places" where you could conceivably do a pub crawl.

IF you are in NYC, don't leave the LES(Lower East Side) or the Village. This goes for food and nightlife. Stay away from times square, do however go to Koreatown my fave restaurant there is Kang Ho Dong Baekjeong.

Caveat, if you want to stay at the Carlyle I won't tell you not to do it.