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Ken started by riding the train from Tirano (Italy) north over the Bernina pass to Pontresina (Switzerland). Then rode his bicycle south to the Bernina pass, then through Livigno and down to sleep in Bormio. Next day he climbed over Passo Gavia and Passo Aprica to return to Tirano, and later that afternoon climbed from Bormio up to Passo dello Stelvio.

train from Tirano over Bernina pass to Pontresina

It might seem like using the train is "cheating", but the train route up the south side of the Bernina pass is more spectacular than the road. Two guidebooks/webpages recommended the train, and two Italian cyclists were on the seats across the aisle from me. We opened the windows and hung our elbows out and enjoyed the view, and it was lots of fun. Anyway I really did use my own muscle-power to climb up to the Bernina pass -- from the north side, admittedly much easier than climbing from the south -- but sufficiently pretty, as in the photos further below.

waterfalls from glacier down from Piz Palu
(visible only from train route, not from the Bernina road)
 

Lago di Poschiavo, from train or road several km south from Bernina pass
 

ride from north: Pontresina up to Bernina pass (2323m)

Bernina peaks above the Mortaretsch glacier, not far from Pontresina (Switzerland)
 

further up on the climb, near Diavolezza
 

Lago Bianco at Passo del Bernina
 

Then descended a little to the south, climbed over the Forcola di Livigno (2315m) to Livigno, then over Passo d’Eira and Passo Foscagno (2291m), and finished with a long (mostly) down to Bormio (1217m).

Next day, Passo Gavia and Passo dello Stelvio