Tuscany-CT-Switzerland Itinerary Sept 2015

You can do your itinerary in this order:

USA > (Airplane) > Zurich (ZRH) > (train) > Bern > (Train via Milan) > Cinque Terre > (short train ride to La Spezia pick up car in La Spezia) > (drive car) > Tuscany > (drive to Florence & return car) > Florence ( FLR) > (airplane via a EU hub) > USA.

Or you can do the EXACT OPPOSITE itinerary.

Since you will be flying from/to ZRH and FLR I suggest to use Lufthansa and/or Swiss International. Swiss International is now part of Lufthansa and both Swiss and Lufthansa serve the Florence and Zurich airports extensively. Lufthansa and Swiss are part of the Star Alliance and are partners with United Airlines. All of the above fly from/to PHL and EWR, which are probably the closest hub airports to you.

Thanks Roberto. That does make sense to me. I couldn't figure out a route from Berner Oberland to CT that would include the Bernini or Glacier Express, but perhaps after I commit to my starting/ending points that will all work out. Great airline info. I'll take a look at that immediately.

Combining the Glacier Express and the Bernina Express to get from Interlaken to Milan is a two day affair. But there other scenic train rides that will get you there quicker without the big names.
1. From Spiez to Brig, instead of taking the new Loetchberg Base Tunnel, you can go by the old Loetschberg tunnel route through Kandersteg. That will add an extra hour to the journey, but that hour will be quite scenic as opposed to the 15 minutes of total darkness in the base tunnel.
2. Take the Interlaken-Luzern Express to Luzern along the Brienzer See and over the Bruenig Pass, then change to a train over the Gothard Pass (with the relatively short Gothard Tunnel) and on to Milan with a train change in Bellinzona. That way is 6 1/2 hours.
3. Take a route that goes from Brig to Goeschenen and change to the route mentioned above right before the Gothard Tunnel. The section from Brig to Goeschenen follows the same route as the Glacier Express without the famous name (and mandatory reservation fee). Also 6 1/2 hours.

Recapping, the fastest way from Interlaken to Milan is 3 hours, route 1. is 4 hours, routes 2. & 3. take 6 1/2 hours. More scenery equals more time.

I recommend the train up to the Jungfrau Joch (spelling?) but check the Jungfrau weather channel in Interlakken before you go. In August 1993 we left Interlakken in beautiful weather but were caught in a whiteout on top. On the way back we walked several miles down hill from one train stop to another but were in fog most of the way. Having said all of that I would still do it again even in the weather. It is pretty impressve that the train stops inside the Eiger and they let you out to walk through a tunnel to the outside of the Eiger Wall...

Sam, your suggestions were really helpful and I have been looking at those options. Perhaps one of those routes Interlaken to Milan to Parma (a full travel day) and staying in Parma (or Modena to see Galleria Ferrari and the new Enzo Ferrari museum) for a night or two, then head to CT. Maybe I'll get some comments about that idea. And rwp: I definitely want to take the train to the top of the Jungfraujoch. Hopefully we will get a good day.

It sounds doable so far.