Cycling around the Bodensee in three-and-a-half days together with a cycling Sherpa named Helena.
If I remember correctly, this border-crossing trip took us from Austria into Switzerland and Germany on Day 1 (80km), from Germany back to Switzerland and into Germany again on Day 2 (90km), then along a long stretch in Germany on Day 3 (110km), and finally from Germany back into Austria (at Bregenz). Instead of stopping after the Full Circle, we cycled on from there along the Rhine to Feldkirch, leading us through Switzerland one more time. This made a total of about 320km in 3.5 days!