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Boston or Philadelphia

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In a few months my friends and I will be going on a small road trip from Toronto to one of these destinations. Which one would be best to go to for a 4 day weekend?

Which city has a better a better nightlife? Which one just has better things to do in general? Also I'm partial to cool old architecture, should that even be a consideration when going to one of these cities?

I'm deciding between these 2 because they seemed to be like the best cities in the north east US with in reasonable driving distance, so I'm open to any other suggestions. I intentionally left NYC out because that will be another trip.
>>
go to Pittsburgh instead
>>
>>1209132

Pittsburgh is nice
>>
>>1209125
>nightlife
>boston

everything closes at 2am.
boston is comfy though. I'd suggest dinner, a couple bars between harvard sq, and davis. tasty burger and be in bed by 3am.
>>
>>1209158
>>1209132
What's good about Pittsburgh? Better than Boston or Philly?
>>
>>1209177
I don't know if Pittsburgh is "better" than Philly or Boston, but it's a surprisingly nice place for a Rust Belt town. It's got some interesting local culture and style, good food (including old guard Italian- and Greek- American joints) and a nightlife scene. And it still has neighborhoods that have their own feel and flavor. The problem is many of them are separated by rivers, so getting around there requires driving over a lot of bridges which can be confusing if you don't know the town all that well.

Boston and Philly are both easier to navigate without a car, Philly probably being a little easier. Both have historic shit to see and decent places to go out drinking after you've seen it. If you like Italian-American food Philly is a great choice. (A Philly roast pork sandwich with broccoli rabe is a thing worth having at least once in your life, and a good Italian cold cut hoagie is one of the country's great sandwiches). Boston has a slightly more international feel, and being New England it can seem more button down and preppie than Philly.
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>>1209125
NYCer raised in Syracuse-Rochester. Unless you are driving with 4 people and bringing down cases of beer and rillette any of the proposed drives (including Pittsburgh) will be boring as fuck and not worth it. If it's between now and April you could be hit with a late season storm and drive time will double. I would take a shuttle flight if possible since it is faster, more resilient to weather with comparable cost since you'll have to pay a non-trivial amount to park your car at a hotel. If you don't need parking then you'll have more flexibility and can get better deals.
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>>1209867
Thanks for the info. Probably going to stick with Boston or Philly, but Pittsburgh seems like a decent trip some other time.

By the sounds of it Philly is winning purely based on the food.

>>1209901
There will be 4 of us on the trip making it cheap. The cheapest plane ticket I found was $230 Canadian per person, while the gas money would be around $100 for everybody making it much more affordable. We were thinking of going mid to late May, so maybe we would miss a lot of the shitty weather?

I hear highway 20 is scenic (the one that runs parallel to the I90). I was thinking of going on that on for about 200 kms (between Auburn and Albany) if we do go to Boston just for a change of scenery. Thoughts? or is it still boring as fuck?
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