Why the specific order? Where are you flying to to start your trip?
I would be tempted to fly to New Orleans first and then rent the car and drive to Memphis then east through TN then to Atlanta. From Atlanta head for Pensacola and then west to Mobile and Gulf Shores then north to see Birmingham and Montgomery before heading back to New Orleans.

Whys that? I thought the order above was just logical based on the map.

BTW, I'm flying to Memphis, TN to start and going down the list.

Unless you deviate a bit that drive from NO up to Memphis is about as boring as watching a mud hole dry up. However, you could certainly go a somewhat more "scenic" route as long as you don't mind seeing a few oil refineries; upriver through Baton Rouge and then to Natchez/Vicksburg, etc.

I'm confused. I'm not going from NO to Memphis? I am from NY.

I'm flying to Memphis, ending at NOLA, and flying home.

Sadly the SE doesn't have a reputation as being good for people who are really into beer. For example:

http://en.wikipedia.org/wiki/Beer_in_Alabama

Beer in NOLA isn't super exciting either if you're looking for local brews. Abita is okay. But I'd rather go to Crescent City even though the beer is also just okay. For non local brews and a really really good beer scene, check out dba off Frenchmen street. If you're into beer in NY, you've probably been to dba at home. The NOLA location is really cool/cozy and often has live jazz (so you may be prepared to pay a cover charge). dba is my favorite beery hangout in NOLA.

Louisiana Pizza Kitchen in NOLA is bad for healthy eating but fantastic for pizza and for their wine selection. Or you might want to try WINO...have walked by several times but have never been inside. note: eating in general is not super healthy in NOLA.

http://www.winoschool.com/

Curious why the stop in Montgomery? I lived there for 6 years (end of high school through college, left in late 90s). For certain make a stop at the Civil Rights Memorial and the Alabama Shakespeare Festival (even if you're not going to see a performance). You could pay tribute at the Hank Williams Memorial. But we used to drive to Birmingham or Atlanta whenever we were looking for something "to do."

You may find that flights to Hartsfield (Atlanta) are cheaper. You could fly to Atlanta, see Atlanta and then take the Amtrak Crescent to Montgomery and rent a car there for the rest of your trip returning the car where you rented it.
I am concerned with the cost of a one way car rental.
The Crescent terminates in New Orleans at the Amtrak/Greyhound station which is next to the Super Dome. If you are just seeing the city of New Orleans, you don't really need a rental car there

Sweetwater Blue in Georgia is very good. [http://sweetwaterbrew.com/brews/] They distribute to Florida (first had it in Pensacola).

New Orleans is the home of Blackened Voodoo beer, which is good, from Dixie Brewing Co. The regular Dixie brew is [yawn] unexceptional. Abita is the better brewery for run-of-the-mill offerings.

More here: http://beerme.com/

I'd never recommend Amtrak anywhere but the northeast corridor - service is weak and it's rarely on-time.

In Pensacola, go visit the Naval Air Station.

Mobile, Gulf Shores (note the "r" - it's not Gulf Shoes - those are called "crocs"), Pensacola - all good for fishing. Same for Gulfport/Biloxi area you'll pass through en route to New Orleans.

If you go to Birmingham eat at Frank Stitt's Highlands Grill!! He also has several other restaurants there.
We recently did the drive from Charlotte to Pensacola, and to say that south of Birmingham is boring is an upgrade.
Pensacola was interesting.
I am not quite "getting" this trip. The choices are interesting I am sure, but I am not sure about it as a "tour".
The Civil Rights memorial in Montgomery is indeed very worth a stop--if you are going there.

I do think that most of your destinations are within your 4 hour drive idea.
Atlanta is far from my favorite place but maybe for younger folks it is fun.

While in Nashville, you can visit "music row" in the evening hours. Park your car then head down the section of Broadway where there are rows of bars that you can go in and out of until you find live music you like - which won't be hard. The bands change about every 1-2 hours in each location. Also, if you can get reservations at the Bluebird Cafe to see up and coming singer/songeriters, it's well worth it. As I recall, it's a bit of a drive outside downtown.

I choose these locations because I can't find an individual to help me select cities and states to visit. So i'm just going to wing it I guess.

Nashville has a few breweries, actually - Yazoo is the oldest and most popular one and is located in the Gulch just outside the main downtown area. You can take tours and/or visit their taproom (I think the taproom is open Thursday - Saturday evenings?). There's also Corsair Distillery if you're into that. Arrington Vineyards is a drive outside of town, but is a great outdoor space to visit on the weekends. They often have a jazz quartet or something similar playing, and they have free tastings (though there's usually a wait to do them).

The Bluebird isn't downtown, but it isn't far - 15-20 minutes depending on traffic. Depending on what kind of music you like, you can either take your pick of the downtown bars or see which acts are playing at the various venues around town. For outdoors, you can go to Radnor Lake, which is a state park completely within the city limits. There's also Percy and Edwin Warner parks, which have several hiking trails. The Chattanooga area (especially around Lookout Mountain) is probably a better bet for outdoor activities.

As far as healthy eating goes, Nashville has a ton of great restaurants, but they're not always geared toward healthy food. What do you define as "healthy" - vegetarian or just not heavy/greasy/etc?

Land in Memphis, drive to Nashville. Go NOLA after that. I could suggest you go to Charleston also, starting in Charlotte. Fly from Charleston to Nola. Then fly to Nashville, and if you want go back to Charlotte. OR book an open jaw.

NOLA, Charleston, Memphis, and Nashville are all great suggestions.

>> I choose these locations because I can't find an individual to help me select cities and states to visit.

That's what these forums are for! Maybe if you take a step back and explain what you're hoping to get out of the trip (and when you're going to take it), that might help a bit.

Honestly, for beer, healthy eating, music, and outdoor activity, I'd personally suggest a trip to the PNW (Seattle/Portland and environs). But there must be a reason that you selected the south.