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Zermatt to Milan thru Parma to Florence

Such an amazing source of knowledge here, thanks all! In two weeks our family is flying into geneva then taking train right to montreaux for a couple nights. Looking forward to christmas market and wanting to book chocolate workshop in Gruyeres (worth it? better than tour for teenage boys?) then train to ski in Zermatt. After, we were planning to take high speed train to Milan then get car and explore around Parma area, stay in agriturismo then fly out of Florence. I'm new to the Swiss train system and wondering first- where is most reputable/ cost effective place to purchase tickets online? When i looked for zermatt to milan, looked like possibly the train gets in late afternoon so thought to spend that night in milan (wasn't really of interest to us but will probably be beautiful for christmas?) then get car next day and do cooking class outside parma, eventually drive to florence to return car and spend two nights there. I guess my question is, is what I'm seeing correct that I cant' get to milan until late afternoon. if so, is it even worth taking the time to rent car (our preffered method of transport in italy) our just adjust trip for train travel thru parma to florence.

Thanks in advance for any info!! i enjoy planning european trips, but this one was pretty last minute and i'm struggling with the trains and final itinerary.
also- any info on ski passes/ lift tickets and rentals in zermatt would be appreciated!!
Thank you!