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Germany -Preliminary Planning 2 weeks in Sept/15

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Myself and 3 friends are in the preliminary stages of planning a 2 week trip to Germany in September. My one friend was born in Ulm, but has never been back since moving to Canada as a young child. We have 15 days/15 nights (excluding flight days). My German friend wishes to spend a couple of days visiting her relatives while the rest of us spend some time on our own. My friend's relatives are just north of Ulm in Weidenstetten, and also in Kehn, on the west border by Strasbourg.
We are trying to figure out the logistics of our itinerary. We were thinking that it might make sense to fly into Munich, spend a couple days there, then travel on to the Ulm area, then Stuttgart (maybe the other 3 of us could spend some time there while our friend visits her relatives, or do day trips from the Ulm area). From there, travel across to the west border to Kehl (again she can visit a relative or 2 for a day), then we can travel down through the Black Forrest area and loop back across towards Munich with our return flight from there. We are all 50-something.
1: If we did this loop, would there be enough to keep us busy for 2+ weeks? or are we limiting ourselves too much?
2: Is there enough to keep the other 3 of us busy near both Ulm and Kehn?
3: We were thinking of using the train to get around - again, would this be limiting ourselves too much by not renting a car to get around? None of us is crazy about doing the driving - the only one that knows a little German, is our German -born friend. How easy is it to get around driving in Germany when you are not familiar with the language?

We welcome all comments or suggestions. We have as yet, not booked our flights but are very close to doing so.

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