Which road?

So there's a lot to do before even thinking that this monumental change is possible.  But, many times I tend to start at the end.  That is to say, I've been checking prices for rent in NYC, looking at the Metro costs, and figuring out to to get to New York to begin with.  That being said, I've mapped out a few road trip routes that I could take.  The first one is my southern dream road trip, going to a lot of natural sights, along with some cities that I would love to see:

#1) Go to Google Maps, and put in the following as destinations in order:

San Francisco, CA

Monterey, CA

Sequoia National Park

Pahrump, NV

Bryce Canyon, UT

Grand Canyon (choose A)

Meteor Crater, AZ (choose A)

Carlsbad Caverns, NM (choose B)

New Orleans

Pensacola, FL

Savannah, GA

Myrtle Beach, SC

Virginia Beach

Salisbury, MD

Washington DC

New York, NY

The second and third options are minimalist road trips, starting in San Francisco, and Los Angeles:

#2) Go to Google Maps, and put in the destinations:

San Francisco, CA

New York, NY

#3) Go to Google Maps, and put in the destinations:

Los Angeles, CA

New York, NY

I'm still trying to devise a route along the northern part of the country.  Any suggestions for landmark would be appreciated.

Cheers,

-Peter