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14 days from Ascona - Italy -Switz

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Good morning.

We are planning a two week trip end of June/July from US that has to begin/end in Zurich (business travel). The first 3-4 nights must be in Ascona, then free to explore. We'd like to do the following, and not sure the best way, especially the Swiss Alps stay. Will be traveling by train and hired car as needed. We could take a train (I think?) from Ascona through Alps, tut then we'd have to work our way all the way south to Florence. Seems the more logical route is to plan Alps between Venice and Zurich? Here's the wish list and thanks for suggestions!

Ascona - 3-4 days
Florence - 2 days
Tuscan town for wineries - 2 days (which is best given itinerary and no car)
Venice - 2-3 days
IS THERE A TRAIN THAT'S BEST THROUGH ALPS ENROUTE? TOWN TO STAY ENROUTE?
Swiss Alps - 2 days
Zurich - 1-2 days - DEPARTURE

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