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Advice wanted on how to plan a multi city trip

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Can someone give me advice on the easiest (and cheapest) way to do this...

I'll be leaving August 30th for a multi city trip. Hotwire only allows me to enter two cities (and tells me the cheapest price is way more than what I know it'll cost for the entire trip)

The dates aren't set but the cities are. I have to be in Indianapolis, IN over Labor Day Weekend for an event, the rest is negotiable. Here's a general idea of my trip:

Seattle, WA ------ > Indianapolis, IN
Arriving August 30
Departing September 3

Indianapolis, IN ------> New York City
Arriving September 3
Departing September 7

New York City -------> Philadelphia, PA (via train, no flights involved)
Arriving September 7
Departing September 11

Philadelphia, PA -------> Washington DC or Baltimore, which ever is cheaper to travel to and stay in. We'll be seeing both cities so doesn't matter where we stay. (via train, no flight involved)
Arriving September 11
Departing September 15

Washington DC/Baltimore --------> Seattle, WA
Arriving September 15
Home so no flight out

Furthermore, when should I book all of this so I can get the best deals while still ensuring I can get a seat and a hotel in all of these places?

One last thing... Does anyone know where I can buy tickets for the train from NYC ----> Philly and Philly -----> DC/Balt? Is it just an Amtrak or is there another train that connects the cities which may be cheaper?

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