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last minute switzerland and italy

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I am a South African woman currently living and working in Dubai. I have now decided not to go home in July-August. Would like to spend +- 3 weeks in Switzerland and Italy with my 20year old daughter. This is my first trip to Europe in 30 years, and I know I have left it rather late, so all support and guidance will be most welcome!
To date I have made only one booking: 3 nights in Florence, leaving there 1 August.
Our plans are roughly:
1 week in one small town in Switzerland - possibly Wengen area
1 week in small town in Tuscany
1 week divided between Florence and Venice
I think it will go like this: fly in to Zurich, train to Wengen. Wengen to Venice, Venice to Tuscany, then to Florence (still Tuscany ... I know, but more like a city), fly out from Florence,
I do NOT want to: rent a car, go to a beach, shop (except for food and wine).
I do not need: hotels with spa / turn down service / fitness centre. If I want a chocolate on my pillow I will put it there myself :)
I love: long walks, rooms with views, nature, history, art ...
I need to find: accommodation in towns with trains and/or buses - preferably small cottages in town. Of course well-run and non-pretentious hotels can also be nice.
My budget: accommodation between 100 and 130 Euro per day (yes I know...)

So, my questions:
I believe that you see more when you do less. However, I think that the train from Switzerland to Venice passes through Milan. If I shave off one day from switzerland, I can stop over in Milan to salute 'the last supper'. Will this be a good plan?
Where to stay in Tuscany and Switzerland? Interesting small town, with railway connections, with budget accommodation, with views, with good walks? Any recommendations?
Venice: it seems as if it can be much cheaper to stay in surrounding areas and travel to Venice every day. However, I think that it will be worth the extra expense to wake up in Venice for four precious mornings. Am I wrong?
PLEASE help me plan! I will be truely grateful for any comments and guidance.

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