I’d take the week in Detroit. I’ve been there, and wasn’t impressed, but if I get to pick the hotel, etc., it could be a fun week.
Just out of curiosity, what makes you say that? It’s one of my favorite cities to drive in because it’s so drivable compared to cities like Chicago, Mexico City, San Diego, Oklahoma City, Austin, Orlando, Dallas, and other places that driving sucks in.
I’m not a big fan of big cities, and I’m not in any condition to take the surprised that would come with it. But I’m pretty sure I could sell the trip for more if given the opportunity, so I will accept.
I can’t imagine Detroit being so bad it isn’t worth $300. Go up by an order of magnitude, and then maybe there’s a debate.
Turning left in Detroit is very confusing to some people. It’s not like a roundabout, where you’ve seen something similar before - it’s just completely alien to them.
For those with no idea what I’m talking about: Michigan Left Turns
Tiger Stadium is fantastic. Ford Field is pretty awesome too.
Shhhh, don’t give them a heads up on the greatest thing we have in this state. It is always awesome to see out of towners completely mystified how to use the Michigan Left.
It works, biatches.
I might take the money over Flint. tough one. Probably depends on whether the hotel has an indoor swimming pool.
Don’t mean to be rude, I just don’t know anything about flint, or what entertainment might eb available. And I’ve read too much about people going into rabbit starvation from eating what they could grow int heir back yards. . .
Never been to Detroit, and I’d take the cash. Not because “dude, it’s DETROIT. ICK”, but because unlike some other cities, there’s not that much that I’ve heard of there, that makes me eager to go there. Like many other cities, there’s doubtless plenty to do there, but I’d keep the 300 bucks, go out for a nice meal or two here, and relax at home.
The same could be said for any number of other cities in the US. Just picking some at complete random because they popped into my head:
Kansas City
Des Moines
Miami
Albuquerque
Sacramento
Portland (OR or ME)
Albany
Buffalo
The Erie Canal 
Louisville
Saint Louis
Fargo
San Antonio
and hundreds of others
If I had friends or family in Detroit (or any of the above), obviously my answer changes.
I take the holiday. I like transatlantic flights (free films, free wine) and I love luxury hotels. I’d also be interested to discover more about Detroit’s social history and the current activism that I’ve heard about. (I’d be one of THOSE obnoxious middle class lefties, hanging out with the proles. )
Editing my own answer: I put Erie Canal as a joke because of the cities just above it… but I might actually get a kick out of a jaunt down that (is there still any boat traffic???).
I’d go to Detroit. There must be some decent restaurants and bars, and there’s the chance to see major-league sports.
And the Michigan Left Turn doesn’t faze me. I recall encountering them while driving through Michigan before; and even though our roads here are not set up for them, some people do them anyway.
Most American cities go to great lengths to purge any tendency to u-turn from the populace. It’s very difficult for most of us the accept it as a preferred alternative.
My choice of hotel, restaurants, and activities? I’m gonna rack up way, way, way, way, way more than $1000, in just about any city in the world I’m willing to bet. With the responsibility clause in the OP, I don’t see how this is even a question … unless you really needed the $300 …
I mean, really, you’d spend the $300 at home, eating out a couple of times and chilling. You could at least do the same in someplace new! Of course when you say it that way, I guess that explains why I never spend the night in the city and always just go home. :smack:
Since the conditions of the offer are that you stay within the city limits, I’m not even certain that you’d see a Michigan left. They’re mostly confined to the suburbs. I suppose there’s Eight Mile, but if you’re heading westbound you’re on the suburb side, and thus breaking the deal. Maybe on Dix in SW Detroit if you’re leaving Mexicantown and getting into the Middle Eastern part of town… (FWIW, Michigan lefts should be everywhere. They make things so much faster, that driving outside of the metro area often infuriates me.)
The law here (and I think it’s UVC) is that unless marked, U-turns are fine. What’s wrong with them? They’re perfectly handy.
I could have a lot of fun in Memphis with 300 bucks and still snuggle up in my own bed every night.
The week in Detroit, once my bar tab was covered I could “earn” the $300 in a couple of nights. 
I’m with Silenus. I can go to Vegas and turn that $300 to $3000 in 24 hours or drink with Sil on our last $20. Win-Win.
Detroit has casinos, if that helps.
Shit son, I’ve spent 300$ plenty a times before on just one night out with me and my beaux. A whole week, all expenses paid? Fuck, I don’t care if it’s bumfuck, nowheresville. Shit is gonna go DOWN!
Hmmm…170 miles to Vegas or 2200 miles to Detroit (while driving through Vegas).
The $300 just might cover for gas to Detroit. Hope the drinks are free there…
One second thought, I think I will save the money on gas and stay in Vegas…and tip those hawt waitresses at the M resort.