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Recent college grad here with about 2 weeks left to enjoy myself

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Recent college grad here with about 2 weeks left to enjoy myself before entering the workforce. I've got about $600-700 to spend on a trip, and I'd love your guys input on it. I'm down for some place to self-reflect and challenge myself; I've studied abroad in Spain and traveled quite a bit, so a destination that's less touristy is preferred.

I was thinking maybe a road-trip to visit friends in DC, then Boston, and NYC. Otherwise, maybe Toronto? I really don't know how to pick and choose options.
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>>1117296

You could start by telling us where you'd be leaving from.
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>>1117303
Shit, totally forgot. Leaving from Northwest Indiana (about 20-25min from Chicago).
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>>1117296
There's certainly plenty to do in DC every day of the year, festival/museum/restaurant and historic wise. But summer in ANY mid-Atlantic to Northeastern city is miserable. Go now, and the more northern the better. Go look at the weather forecast and see if you would enjoy pounding the pavement for 12 hours of sightseeing. Hanging out in some dudes houses? Air conditioned car to air-conditioned buildings in suburbia? Manhattan? No. Boston? No. Smithsonians? Go early, leave late. That's not so bad.
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>>1117323
That's a good point, I didn't really worry about the weather too much, but it's a critical factor to consider.
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Any thoughts on other travel options?
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I will be taking a vacation to DC in mid July. Would also appreciate any input as to interesting sights, events, things not obvious to visit.
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Bbq tour in the south

About 5 years ago my brother, his friends and I went on a road trip through the south, I've since been on many other road trips, but this one was by far the coolest
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