New York to Cali and Back in 4 weeks?

OK, so my girlfriend and I want to roadtrip this summer, never done it before but I've driven 200+ miles in a day multiple times, and I've done NYC to north of Montreal straight, so I'm not real worried about the driving. We don't want to plan the activities, but the basic things we'd like to do:
1) Drive as much of the old rt 66 as possible, ideally from the chicago area to LA pretty much, drive this on the way there.
2) Drive from LA up to the Bay area, we have friends there.
3) Drive from the Bay area to the denver area (family), possibly going through Las Vegas, but that's not imperative
4) From Denver, start heading back to NYC
5) We only have two sites we want to see as of now, the Grand Canyon and Yosemite, other than that we're content just seeing what there is to see on the road/along the way.

Is 3-4 weeks enough to do this? How feasible is it to do minimalist hotel/motel room stays (primarily to save money, any night we can avoid paying $40 to sleep and save a couple hundred overall would be wonderful), instead just trying to find truck stops/hospital parking lots to sleep in? Thanks for all your help, sorry if this is a post some of you have seen the likes of 100 times :)

Welcome to the RTA Forum!

A few thoughts right off the bat, if you want to hit Vegas, it would make a lot more sense to hit it on your way out to LA. It would be a relatively short detour from I-40/route 66, at least when compared to a direct route back from the bay area to Denver.

If you are looking to save money on sleeping expenses, camping is certainly my favorite way. That should cut your nightly expenses down to $20 or so a night, instead of the $50 or more a night you'll likely be spending at motels.

Let me add that one of the other big expenses when traveling is food. We often suggest that people eat out of their cooler. If you decide to camp, then plan to cook some meals at your campsite, too. You can get some hints about eating healthy good food at a reasonable cost here. At the beginning of that post is a link to another post where you will get some tips on how to figure out a budget for this trip.

You seem more into the idea of being on the road than on the sights to see. That's cool. And it will make it easier to make this trip in the 4 weeks at a comfortable pace. I would suggest figuring out how many days you'll be visiting friends/family and stopping at Vegas/GC/Yosemite. This should give you roughly how many days for the drive. I would suggest considering something like 8-10 days each way for the drive to make it leisurely enough to allow yourself time to explore along the way. (It takes about 5 days to cross the US in a speed run.) This would leave you 8-10 days for the visits/stops you have planned.

Excellent, we're only 19 actually, I've been to Vegas once before and she wants to see it just to see it, but since we can't really do much there we're not sure if it's worth a detour. 8-10 days each way sounds reasonable, giving us room to spare to visit with people. I've done minimal camping (at most an overnight) and don't own a tent or anything...how easy is it to just find a place and set up for the night? Camping is really a viable option, in terms of reliably being able to find somewhere along the way? Thanks for all your help everyone!

OK - so we just got back from our trip and I figured I'd write a follow up, since our trip seems like a pretty standard coast-coast trip that could be used as a prototype.

Traveled 7960 miles in 28 days, spending a week going from coast to coast, two weeks in cali, and one week getting back.
Spent $4700, which breaks down as such:
$1500 on lodging (but we spent roughly half of our nights at friends/family, the other half in $100 a night hotels/motels)
$1000 on food (family fed us occasionally, probably paid for 3/4 of our meals)
$900 on various expenses: sightseeing expenses, souvenirs etc.
$1300 on gas (at about 4.05 a gallon avg, roughly 25 mpg, expected to get only 20 mpg so we had lots of left over money here)

Major visits included : Grand Canyon, L.A., Monterey, San Francisco Bay Area, Yosemite, Denver, Chicago.

All in all the trip was a blast.

Hope this helps anyone planning a similar trip.

We appreciate hearing back from people. And I'm happy you had a great time.