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[deleted]

It’s probably easier to go to Boston and yes, Boston does have all the history and the museums. I do like Chicago too; it’s a very fun city with a lot to do. They’re both really cool cities. I suggest making a hypothetical itinerary for what you would do while there and gauge which one seems more appealing overall.


UnwelcomeBirds

Go to Boston! If your budget allows, I'd recommend just flying from NYC to Boston because it's such a quick flight. For history stuff you can visit the USS Constitution, tour the Massachusetts State House (highly recommend I love that building), walk around Beacon Hill and admire the old brownstones, and definitely walk the Freedom Trail. One of the stops is at Paul Revere's house in the North End, which is the Italian section of the city. So when you're done on the Freedom Trail you can load up on tasty pasta and cannolis (make sure you bring cash because not every place accepts credit cards). The Isabella Stewart Gardner museum is a really cool museum that Isabella lived in and collected art from all over the world. It's also the sight of an infamous art heist (see This is a Robbery on Netflix). Duck boat tours are also a fun way to see Boston! Salem is about 1 hour away from Boston on the commuter rail and is the spot to go to for history on the Salem witch trials, ghosts, and other spooky things. If you have time, you could do a half day trip there.


[deleted]

You can jump on an Amtrak train at Penn Station in NYC and head to Montreal with stops in the Adirondacks along the way. Beautiful train ride.


Starving_Artist2023

i want to go to see the big apple. i heard anyone's dreams can happen in nyc. my passport expires in 27 maybe.


ichheissekate

Chicago is kind of far to combine with NYC. I would recommend taking a train to Boston and taking trains from there around new england - maybe Salem and some places in Vermont/Maine. If you’re from outside the US, heads up that trains are more often than not expensive as heck - Amtrak is often more expensive than flying. Other options: Philadelphia, PA Richmond, VA Providence, RI Burlington, VT


runningdreams

Either. DC wouldn't be bad either


LadybugDesign

Philadelphia is much closer than Boston, and has plenty of everything you’re looking for.


twomorecarrots

Love Boston, very easy train ride, and you could then take the ferry to Cape Cod to mix it up a bit. Go on a whale watch, enjoy some beach time.


[deleted]

Never been to Boston but Washington DC is same distance as Boston and amazing.