1.I wanted to apply for ESTA early BUT the application form wants me to key in my flight details when I have yet to decide them. Hence, stopping me from applying. Am I able to just fake it?
DO NOT DO THIS. Don't f*ck around with USCIS (the immigration department), they WILL put you on the next plane back.
An ESTA lasts for two years once you apply for it. You can hold on until you actually book the flights, and you can apply for it as little as a week before you fly. Better to wait until you know what your details are.
2. I'm not familiar with seasons (months), so I guess those months around winter would be cheaper?
Then, would having about S$2k be good enough? I really wonder.
Mmm... yeah, $2k (plus the cost of the flight) should get you through two weeks with plenty of room.
Winter in the northeast is kind of miserable, though. Those poor suckers are buried under two feet of snow right now - meanwhile out in California we're all like "snow? what's that? let's go surfing!". If you want to do the east coast, do it in spring/summer instead - let's say April to July. (The later in the season you go, the closer you get to hurricane season, which can put a bit of a dampener on your holiday if you want to tack on a leg in Florida.)
Update: also, the earlier you go in April or into March, the more risk you have of running into hordes of drunk college co-eds on Spring Break. This may or may not be to your liking, depending on whether your holiday itinerary involves hooking up with drunk college co-eds, but either way it'll drive the price of hotels up.
4. Any average cost prices of food?
Not as cheap as Singapore, but still pretty cheap. Call it ten bucks US for breakfast and lunch, 20-30 for dinner.
5. Thinking of getting a car in case I plan to drive to Washington DC or St Louis (have another friend there).
People: if you're going to ask questions about getting between destinations, look at Google Maps first.
America is huge. Like, it's really really big. The record for driving across it is
a shade under 29 hours, and that's averaging
150 kilometres an hour. You will not be doing 150. Realistically, end-to-end across America is a four-day non-stop drive; if you wanted to make a road trip out of it, you could easily turn those four days into four weeks.
NYC to St. Louis is
fourteen hours of non-stop driving, according to Google Maps. Now, I love my road-trips... but if you're going to do that trip, you should save yourself two days of travel time (and a few hundred bucks of fuel and one-way rental charges) and fly.
Would be more beneficial to travel by car right? Or would doing bus/train rides be semi-fast and way cheaper?
For NY to DC, always take the train - the Amtrak Acela service is fast and cheap. For anywhere on the SF-LA-LV triangle, you can drive, because all three legs of that triangle are great drives (okay, maybe not LA-LV). For everything else, there's Virgin America.
Generally you want to avoid the buses in America, as well; they tend to be full of crazy people and ex-convicts.
Also those cars are left-side driving cars, anyone face problems with driving those? I'm familiar with right-side driving here in Singapore.
Nah. It takes like an hour or so to really get used to it, but once you've done that it's just like riding a bike - and you'll probably be doing most of your first drive on the freeway anyway, so it's not like you have to worry about oncoming traffic or anything. My parents did a huge four-day road trip when they came over last year, and they're both the wrong side of seventy and they've never driven on the left in their lives. Went off without a hitch.
7. How much does it cost to get mobile data there? What is the process like should I want to get a prepaid plan there?
Budget about $30 for a monthly iPad plan, or $50 for a monthly voice-and-data plan. Basically you just rock up to the AT&T store, tell them you're visiting, and ask them for a GoPhone SIM; if they won't help you, go to T-Mobile, tell them you're visiting, and they'll sort you out. Try AT&T first, because their coverage is better; but T-Mobile's a lot more savvy.
Also, are there any apps you guys would download which would make navigation cheap/free instead of having to pay extra for prepaid + GPS Navigation (for the car)?
It's not free-as-in-beer, but I recommend paying the $60 or so for the Navigon USA program. It has full offline mapping, so you'll never lose your way even when you're out in the more squeal-like-a-pig parts of the country.
