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Any tips and advice appreciated - 4 weeks south/east US

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My husband and I are planning our fourth trip to the US this October and I have a bit of a plan, but would love some advice/tips.

Our must do things on this trip - an NFL game, anywhere! Hubby wants to visit Washington DC for a few days. I would love to go to the South and Florida, and somewhere in the Carribean if we could. We are experienced travellers but I'm already thinking this is just too much!! Here is a brief outline of what I'm thinking

3 night New Orleans - pick up car and drive through to Nashville
1 night Natchez
3 nights Memphis
3 nights Nashville
Fly to Washington DC, 3 nights
Fly to Miami, 2 nights, NFL game on the 20th October - pick up car for four days
Drive to the Keys, 2 nights
Fly to Jamaica, 3 nights
Fly back to Florida, Orlando for 5 nights (Epcot, Kennedy Space Centre, Disney)
Fly to LA, one night before returning back to Australia.

A few questions - what is domestic travel like in the US at the moment? Will we be spending hours in airports just for domestic flights? I'm aware of how bad the international airports can be.

For a short Carribean experience - is Jamaica a good place to go? Is there somewhere closer/nicer we could go to?

Is 3 nights in Nashville and Memphis too much? I was thinking as we'd have a car that we could also get out and see nearby attractions, like the Jack Daniels factory near Nashville. Memphis - Graceland, Beale Street and various studios - could this be done in 1 big day (2 nights?)

Is road tripping through the south worthwhile? Should we add more time onto this part and try to get to some out of the way places? Before my husband announced he HAD to go to Washington DC this trip, we were originally thinking of going from Nashville to Atlanta/Savannah or maybe Kentucky... ahhh the options are endless!!!

I love the US - we have done four week holidays every second or third year for the last 7/8 years. I know I can't see everything that I want to in one go, but then I see that we're so close to something (like Jamaica) and think "oh we could just pop over there for a few nights!"

Any opinions would be appreciated. We are young-ish and have always crammed a lot in our holidays, so we're not afraid of being tired and worn out at the end of the month!!

Thanks in advance!!

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