Back to the time of year for your visit, shoulder season, spring or fall, has lower prices and fewer people than summer but better weather than winter. I prefer spring to fall because the days are longer (you can see more). And there might be flowers.

1. Which part of Germany re weather? You want good weather and no crowds? So does everyone else. Therein lies the problem. Late spring or early fall would be OK, but some areas of Germany can be rainy in spring. Keep in mind that while Germany is not a massive country, there are differences in weather from one region to another.

2. When you say "best places," do you mean accommodations or parts of the country? A gasthaus, the rough equivalent of a B&B, can be nice and affordable. There are many small German towns along the Main and Tauber rivers, for example, that are picture-perfect and not too overrun (Rothenberg is in the "overrun" category.) To get to a lot of them, you'll need to drive, which answers part of another question. I have found rural Germany to be some of the prettiest, most affordable parts of Europe.

3. It depends. Where are you going? You need to answer that question first. Another nice thing about Germany is its central location. (Hitler noticed that, too.) France, Austria and Holland are within easy striking distance.

4. Besides here: I like the above recommendation about using the services and information of the military installation. Depending on the size of the installation, they could have some handy info.

I would suggest that, since this is your first time in Europe, that you start with Weisbaden itself. It's on the Rhine River and there are wonderful cruise ships that ply this famous wide river. My preferred cruise line is the KD line:

http://www.kdrhine.com/

But there are several other cruise lines if the KD schedule doesn't work for you.

You could do a day trip, for example, to Rudesheim, which is really easy to reach via the river and only an hour out of Weisbaden:

http://www.rudesheim-rhine.info/

Or you could plan to go for several days along the Rhine River and overnight in river towns like Bacharach.

There are a lot of old castles atop hills and this is one of the most scenic cruise areas of Europe.

As for lodging, do what a lot of Europeans do and take the suggestion to stay in a gastehaus (a "pension" or a B&B). They are relatively inexpensive and Germany is dotted with them. Each town has a tourist office which will list the available lodging. Below, for example, is the city lodging directory for Weisbaden:

http://www.wiesbaden.de/en/tourism/a...tion/index.php

Another good source for B&Bs is tripadvisor.com. Instead of looking for "hotels", look at their listings for "B&Bs". There are reviews attached on tripadvisor and these reviews are invaluable in helping you in making your selection.

If you want to go to another country, the suggestion to fly "open jaw" is a good one. You can either begin or end your trip in another country other than Germany.

Good luck on your planning!

Buy several German Guide books, we prefer Fromers but there are many more available, check the date of the edit to get a better idea of prices and schedules; get a good map of Germany; stay in Germany to save money and time, with only two weeks total you won't run out of things to do. Purchase Twin German Rail Passes. When you pack, take out half the clothes and put in twice the money. Have fun.

<<- Ask your son to check with the USO at his military installation for bus trips. These trips go to many popular locations and usually are all-inclusive - transportation, hotel and some meals. They are also reasonably priced. This may be an easy way for you to travel with or without your son and not have to worry about all the arrangements.>>

YES - please look into this! My parents (also first and only time visitors to Europe) did this when staying with my brother in the Kaiserslautern area. I believe they went on two excursions including one full day trip to Paris. I know that does not sound desirable to many on this board but it was perfect for them.

Try googling "Weisbaden uso tours" to get some ideas and maybe contact the USO office for more information.

Just want to add, there's no need to buy a lot of guidebooks. Get them from the public library. As PegOTR indicates, Rick Steves' Europe Through the Back Door is particularly encouraging for first-timers.

And there's lots of information on the Internet, like at Fodor's Destinations (click above). Also on the Internet are mapping programs, that estimate how long it takes to drive from point A to point B. You can do this at Google Maps or www.viamichelin.com among others.

You will be able to fill your days with wonderful trips in the Rhein area! Mainz ( a smaller city with beautiful Chagall church windows, a museum holding the first Gutenberg bible, a pleasant town square in the shadow of the cathedral) is just 20 mins from Wiesbaden by train.
Koblenz (at the confluence of the Rhein and Mosel rivers-great wine country with numerous wine festivals in Sept-October) is 1:22 away by train, or better yet,see a scenic castle-rich stretch on a KD Rhine river ferry, while picnicking on deck! Bacharach is a LOVELY small town on the Rhein (served by Untours with one-week stays in vacation apartment rentals)-rich in old half-timbered houses and wine-cafes-just 1;30 mins by train--I stayed here for two weeks taking numerous daytrips.
Touristy Rudesheim is just 33 mins away (worth a few hours IMO), has a nice gentle chairlift up over the vineyards.
Moselkern and the great castle above is 2:20 away (SO worth it!)
Cochem is a gem on the Mosel too!
Start reading about a few of the towns suggested, and see what piques your interests-You can't go wrong!

http://www.k-d.de/english/home/

Check out the boats mokka4 talks about - one of the most popular things to do in Germany - you can get on and off to see some of the castles and cutish riverside resort towns.

And yes Burg Eltz, the castle protruding out of a forest high above Moselkern is one of Germany's most awesome and famous castles - before the euro it graced the back side of I think a 500-mark bank note or some really high denomination. K-D boats also serve Moselkern as do buses or you could easily rent a bike in Cochem and cycle on riverside bike paths the dozen or so miles to Moselkern - then it is a lovely few-mile stroll thru forests up to the castle or a quicker and less demanding mini-bus/taxi ride.

I like the idea of the open jaw flights and checking with the USO. I'm going to digest all the wonderful suggestions you all have provided. Will be back with more questions, I am sure! Thanks to all.