Too much depends on your mode of travel to a certain extent. Sounds like you have been here previously so you know the US is about 20% bigger than Australia and thus travel times here, like there, can be considerable. The rail system is not a terrific option time wise if you plan to travel large distances cross country. But it will be of easy use on the East Coast. Each place you mentioned would be nice for week long visits. ;-) I’m thinking if you budget 3-4 days in each place with a travel day between each that will work out that you can visit much of your list. Please realize that the cheapest flights are often via hub cities so for instance flying from Nashville to New Orleans might look short but the airline might route you through Atlanta. Thus the travel days might be long if you pick cheapest fares. If I were to suggest dropping a place it would be LA. It is a great place to visit but it is a huge area. And though I like Chicago it is not exactly on the way to anyplace else on your list. But it is another great place to visit given the types of stores you like. SF is a very walkable place – geographically constrained by water so the SF proper is an easy visit. I guess my responses will depend a lot on your mode of travel and budget. But on the surface it is probably a few too many places.