IMHO... Milano to Andermatt - 3 to 4 hours. Autostrada to the Swiss border and backroads from there. The Italian Autostrada is pay as you go, whereas the Swiss is a yearly fee of CHF40. Plus the traffic out of Milano is nasty, but opens up nicely once across the border. If the weather's dry, take the cobblestoned old road (La Tremola) over the St. Gotthard. MUCH more flavor. The new road is rather bland. Andermatt isn't what it used to be, but it's still very good. 3-4 days of riding in the local area, so you could definitely saturate your riding in a day or two. I'd really do 2 nights in Andermatt, if the schedule allows. From there to Livigno for an overnight on your way to the Dolomites. (try to get there with as close to an empty tank as possible - cheap fuel). From Andermatt to Livigno. Multiple ways. I'd strongly suggest this route from Andermatt: Oberalp Pass to Ilanz. South from there and east to Bonaduz. LOVELY road along the Rheinschlucht (gorge). The Vorderrhein & Hinterrhein come together at Bonaduz to form the Rhein. South to Thusis, and then: * Towards Tiefencastle and over either the Julier (so-so) or the Albula (my preferred - it plays tag with the Glacier Express tracks and is a more intense experience) * South through the Via Mala, over the Splugen and Maloja passes and past St. Moritz. Note that the Italian side of the Splugen is tight, but a lot easier downhill into Italy. Can be slippery when wet. From Livigno to Arabba - Go over the Stelvio. It's trafficky, trite and crowded, but almost mandatory. At least once. Grab a wurst at the top. I prefer the guy with the orange cover, but the guy with the blue has his adherents. About 250km each day. Dolomites. I like Arabba (and I really like the Hotel Evaldo). It's right in the middle of everything, but has NO nightlife - it's a place to sleep. Corvara in Badia a bit north is more of a town with walking/shopping opportunities.