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A month i USA - where to go and for how long?

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My boyfriend and I are planning a trip to USA in July for about a month. We want to experience as much as possible, and we really need help to make the best of our vacation. Our preferences: We love to just walk around getting to know cities, go shopping, visit museums and landmarks, relaxing by the beach, eat good food and listen to good music. So basically everything. We plan on taking some flights and renting a car to drive around some places.

What our plan is at this moment:

Start in Los Angeles, rent a car and drive to San Francisco (and maybe Las Vegas). We would also like to visit Austin, Texas, The Grand Canyon and Roswell, NM, but we realize there probably won’t be enough time. Then we are planning on flying to Chicago and from there drive to New Orleans (visiting cities on the way), then drive to Jacksonville North Carolina (I need to visit the hometown of my favorite artist, Ryan Adams :p) and drive up to New York and maybe visit Boston too.

We have no idea how much time we should plan for each place, all we know is that we want a full week in New York, which leaves 3 weeks for the rest of the US.

So, what we are hoping you could help us with:

1. Which of these cities should we absolutely visit, and which is OK to skip?
2. Are there some other cities/areas we should consider, maybe some places nearby or on the road to one of the other cities we already are planning to see?
3. How many days do we need in the different cities (I can add that we are used to hectic and intense vacations, but at the same time, we need some relaxing time too).
4. Which cities are the best for a beach vacation? Los Angeles? San Francisco? Other?

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