What to do around Stuttgart

From Stuttgart consider some of the wonderful towns that are closer, like Esslingen, Tübingen, or Strasbourg.
For Stuttgart itself, I recommend this tour company as there is way more to see in Stuttgart that people think.
http://stuttgartsteps.com/

Hi Matt- I believe the Volksfest is going strong the first week in October. It's a 2/3 size Oktoberfest that you might enjoy. Some of the folks at the seminar may be going so maybe you could tag along with them, especially if they have reservations in one of the tents!!.
Have a great trip!!!

Although the Mittelrhein and Rothenburg aren't that far away from Stuttgart, there's also quite a bit of interesting stuff closer. The Neckar river between Bad Wimpfen and Heidelberg is similar to the Rhine. Likewise, any of the towns mentioned by Jo (plus Schwäbisch Hall) provide you with a Rothenburg-type experience, but without the trinket shops and hoardes of bus tours.

Ludwigsburg has a magnificent palace.

For castles, look into Burg Hohenzollern, Schloss Lichtenstein and Burg Teck, plus a dozen or so along the Neckar (most are ruined, though).

I second Tuebingen. The center of the city is pretty to walk around. It is a University town so it has a younger vibe. There are also places to hike outside the city, if you are interested in that. The Neckar river also flows through the town and is really pretty.

I would also suggest the Mercedes Museum in Stuttgart. I am not a huge car person, but the collection they have is amazing. This museum is one of my all time favorite museums. They also do a really good job of weaving development of the car with World events. We spent 4 hours there and could have spent more time.

Porsche also has a muesum there. It has a lot of their racing cars.

The Black Forest is not too far from there either.

Thank you all for you advice
I think I will try and see the Rhine region and perhaps on other days visit the smaller towns you have suggested

Is it better to hire a car or use the train system? Are their toilets on trains?

Also is it possible do you think to do Koblenz, St Goar & Bacharach and perhaps some of the Mosel in one day or would I require more time?

Traffic around Stuttgart is some of the worst in Germany... even though I think it's usually easier to see smaller towns by car, just getting in, out and around Stuttgart can be so painful that rail is probably the better option. Regional trains don't have toilets, intercity trains usually do.

The Rhine plus the Mosel is probably stretching it for one day by rail. Might be feasible by car, but it will get dark before you've seen all of your destinations.

All of the regional trains I was on recently in Germany had toilets, and usually one wheel chair accessible one. Now I didn't look on some of the "toonerville trolley" types like the Hohenzollernbahn in Rottweil, or the Agilis in Bayreuth.
If you use only regional trains, you can travel all day for one price. Just in Baden-Wuerttemberg, a "Laender" ticket is good all day weekends, for 23 euro. To go further afield, the Schoenes Wochende (Beautiful Weekend) ticket is 40 euro for the entire day. That would work to go up to the Rhine area. And I believe you get a discount when you take one of the K-D Rhine cruises.

Details: http://www.bahn.com/i/view/USA/en/prices/germany/laender-ticket.shtml

I too would recommend Tübingen. I had a pleasant lunch at a restaurant on the left bank of the Neckar.

If you go out to the Hollenzollern Burg, you can take the train from Stuttgart Hbf direct to Hechingen Bhf and a bus from there. Be aware that there are only two buses from the Bahnhof to the Burg (at 11:25 and 13:25) and only two back later in the afternoon, so plan accordingly. If you take the 10:16 IRE (IRE 3255 to Aulendorf) from Stuttgart Hbf, you'll get to the castle at 11:47.

Use the Bahn schedule webpage and put in from: Stuttgart Hbf and to: Burg Hohenzollern, Hechingen.

I might also suggest taking the train from Stuttgart Hbf to Freudenstadt Stadt Bhf (via Eutingen im Gau). Freudenstadt is sometimes known as the capital of the norther Black Forest and features an enormous town square (and also a spa). Be sure to get off at Freudenstadt Hbf and take the shuttle up to the Stadt Bhf, or you'll have a steep climb.

Or you can go to Pforzheim and take the train up to Calw, a pretty town on the Nagold river, with plenty of Fachwerk buildings, the home of Hermann Hesse.

Wow so many suggestions and so few days for me to explore
So I really want to spend a day at least exploring the Rhine towns and or the towns along the Mosel

I am looking to start off at Koblenz and either head down the Mosel to Cochem and Beilstein or head from Koblenz down the Rhine to St Goar and Bacharach. Which direction do you think is best?

The following day I could visit Tuebingen, Strasbourg, Esslingen and Freiburg
A friend has also suggested Heidelberg as well. Which towns out of these do you suggest?

Should I visit Rothenburg? Some have suggested its too busy with tourists and there are better towns?

I am also looking to spend one day in Berchtesgaden, as I have an interest in WWII and have always wanted to visit the remains of the Berghof and surround areas/buildings that were used in WWII. I cannot seem to find a train route out this way though, any suggestions?

Thanks a lot for all of your input so far :)

And here's a fourth recommendation for Tübingen. :) The Neckar River valley is quite beautiful. Look for apple orchards!

I think it would be very difficult to do Tübingen, Freiberg and Strasbourg in one day! Each of the cities deserve a day each. I think you'll need to pick. I spent a long weekend in Strasbourg when I was 19 that was memorable for many reasons including seeing where Marie Antoinette spent her night in France.

Pam

Almost nothing remains of the Berghof complex, except some scattered rubble, here and there. The Bavarian government is keen on minimizing the use of the site as a neo-Nazi shrine, so they've obliterated almost all remnants of it and allowed nature to do the rest. You won't even find any historical markers. Kehlsteinhaus, though, is still there and widely visited.

Berchtesgaden is a little far from Stuttgart for a daytrip, however.

If you want to see a little bit of Third Reich history, visit the Thingstätte in Heidelberg. This was built as an outdoor ampitheater in the Greek style for the purpose of holding political rallies. Although it didn't see nearly as much use as the Nazis intended, it has survived almost completely intact. It's a little hard to reach without a car, though.

As for Rothenburg... visit the towns near Stuttgart previously recommended, and then decide if Rothenburg is worth it. You'll see much of the same, plus tons more tourists and souvenir shops.

Thanks for your help everyone
I have pretty much decided my schedule now
I will travel around by train

Day 1
St Goar
Bacharach
(Still deciding on whether to visit Boppard or not)

Day 2
Strasbourg

Day 3
Heidelberg

Day 4
Reutlingen
Esslingen
Tunbingen
Hohenzollern Castle

Does anyone happen to know the best sim card I can pick up with the most data? I want to be able to map my way around with my ipad

Any other suggestions welcomed!
Thanks