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I want to cover Paris-Switzerland-Italy in 2 weeks

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Hi, I know that this is not a good idea, and any of these countries is worth weeks of visiting and years of returning. However, I don't have time.

I am now finishing my last year of college in Abu Dhabi, and before heading to work in Fall in Singapore, I want to visit some key attractions of Europe. This might be my only chance in the next 5 years to visit Europe, so I want it to be comprehensive, but at the same time enjoyable.

My time frame will be from 26th of July to 10 or 11 of August (I know it is the peak of tourist season). Here's a glimpse of what I want to do:

26-29/7: Arrive at Paris and travel around
30,31/7: Go by train to Geneva, stay a night and take the local train to Montreux
31,1/8: Take the Golden Pass to Interlaken and spend the night around this area
1/8: go to Lucerne through Golden Pass and then change to Glacier Express down to Andermatt. Spend the night in one of the stops?
2/8: arrive at Chur and spend the night there.
3/8: spend the whole day traveling through Bernina Express from Chur to Tirano, and then use the local train in Italy to move from Tirano to Milan, and then get a train from Milan to Venice. Spend the night in Venice.
4/8: travel around and spend another night in Venice
5/8: leave Venice early and go to Florence, spend the whole day at Florence
6/8: go to Siena and go back to Florence with a friend, or ask him to go to Florence?
7/8: spend another night in Florence
8/8: wrapping up in Rome: go to rome spend the whole day
9/8: going to Vatican
10/8: travel around a bit and fly back to Dubai.

I have a few questions:
1. How easy is booking cheap hostels for the places in my itinerary? I know this is peak season, but I have 3 month in advance to make reservation. If possible, can you recommend me some ok places to stay?
2. I will travel mostly by train, so is it ok to bring a big backpack onto one of those fancy trains I mentioned? Can I buy train tickets in advance also to get a better price? Do I have to go to each country's railway system website to book or is there a central website for the whole Europe I can go to? How more expensive the panorama trains in Switzerland compared to the local ones? How safe are the trains? What plan should I buy for my tickets or I should go for individual pass?
3. If possible, give me advice on cutting down places or suggesting the good villages to wander around in Switzerland.
4. My budget should be around USD 3000 without air travel in and out of Europe. I will bring 1000-1500 in cash and the rest in my credit card (I will book hostels and tickets in advance). Is it smart to do so given how credit card friendly these countries are? Is it a reasonable budget? I mean obviously I want to make it as low as possible, but I guess I'll spend when I have to. What is the best way to have cash in Switzerland? Withdraw from card or exchange directly from USD?
5. What are the things I should not be stingy about? Food in a good restaurant in Paris? Souvenirs? Chocolate in Switzerland? Boat trips or tours in Venice? Some expensive museums in Florence or Rome?

Thank you for going through such a long post. Any comment is welcomed. I probably end up cutting a lot of things, but it's worth a try to see if I can cover and still enjoy this many places.

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