With that price tag you can aquire a decent R1100GS or even R1150GS. But probably you'll get better conditioned late R1100GS (1998-1999 year models, which will last a lifetime if you service them good).
For 2-up, big telelever-fronted boxer series are the best you can get in that price range IMO, unrivalled comfort and handling when loaded 2-up, especially if you intend to do bad roads time to time (Eastern Europe, the best Europe for GS  ).
Then again you can get a V-Strom 1000 cheaper, but have to make a lot of costly modifications (stronger springed $$$ aftermarket rear suspension and you need A LOT better springs for the front, strong crashbars to protect all that fragile plastic, better bashplate for the exposed oil cooler, etc for a starter) to make it handle under load and to prepare it for the abuse.
Best try different bikes (besides GS and Strom, also consider Triumph Tiger 955i, Varadero that fit that price range) on a long test drive and choose the one you and your g/f feel the best on the long distance.
Happy testing!
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