My girlfriend and I have just booked flights for our trip to the US/Canada, landing in Newark Airport on the night of the 31-Aug and flying out of San Fran on 1-Nov. That gives us 62 days and 63 nights to play with. We're looking to spend about 10 - 14 days in New York and considering that's where our trip begins I thought that would be a perfect place to start planning. I'm mostly looking for advice on NY here but any general advice for travel in the US and Canada would be great too. Here's our general idea:
General Info: We're a couple of Australians in our mid-twenties. I've done a bit of travel to Europe and Asia with my parents when I was younger and my GF has been on a few longer trips to Europe and Vietnam with friends. She has family living in Toronto who we would be staying with for another 7 - 10 days after New York, meaning the first month is mostly if not entirely a trip to New York -> Toronto. Also the two weeks staying with family means we save on accommodation and other costs.
Budget: At this point we've saved around $15,000 AUD (~$14,000 USD) each to take for the two months. Flights in and out have already been paid for. I understand that NYC can be quite expensive but we do hope to make the most of our trip.
Destinations & Duration: New York (14 days) -> Toronto (7-10 days) -> Chicago (4 days) -> New Orleans (4 days) -> Austin (4 days) -> Las Vegas (2 days) -> San Fran (5 days). We have plenty of days left and would be interested in Washington, Vancouver possibly Mexico too.
Interests: Broadway, Standup comedy, Punk and Metal shows, music in Austin, shows in Vegas, All food (dives, street food, fancy, ny/chicago pizza, best BBQ joints), Sport (Basketball, Hockey and maybe some WWE), Museums + all the touristy locations too.
That's all i can think of for now, this is obviously early days but I'd really appreciate any advice. Thanks!