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Need help w/ route for 10 nts Switzerland, before or after Italy!!!

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I really need some guidance on this part of our trip. We're changing our itinerary to take in Switzerland...I have 10 nights, we're primarily interested in the Alps/scenery and small/quaint towns....looking at the Berner Oberland area, would like to work in Appenzell if possible and the Bernina Express. Would also like to do this without a car. (Renting in Italy and don't want to do two rentals) We currently are committed to two weeks in Italy from Sept. 22 until Oct. 6 and I can put Switzerland before OR after Italy.

A few of my questions, and I hope they're clear enough:

1. Putting Switzerland AFTER ITALY we'd be departing from Rome....would it be better to train North, start with the B Express or fly into Bern (budget airline Skywork?) and make a loop to Zurich for our flight home?

2. Visiting Switzerland BEFORE ITALY we'll be flying into Zurich (a short flight - not overnight). From Switzerland we would be heading to Umbria so I believe my best option would be to end in Bern and fly into Rome, making our way to Umbria. (Spello) Or is there a way to work my itinerary to be able to train into Italy, either direct to Umbria or picking up our rental along the route? Recommendations on what route to take in Switzerland?

2. Is one direction better than the other on the B Express?

3. If I add Switzerland after Italy is that getting too late in the season? (Oct 6-16)

4. Recommendations on how/where to split the 10 nights to give us convenient public transportation for side trips. We're staying for a week in two locations in Italy so not opposed to moving around for this portion, although I would prefer no more than 3 hotel changes.

Any recommendations will be greatly appreciated.

Thank you all and have a wonderful New Year!

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