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Rome, Paris? Complex logistics, help please?

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Hi everyone,

First off, sorry if this is really confusing. I have been confusing myself for the past few hours trying to figure it out and hoped maybe someone here could lend some advice...

I am planning my first solo trip to Europe, for about 3 months starting in June. Before I can settle on an itinerary however, I have to figure out a complex logistical problem...

I would like to buy a 4-country Eurail select pass to get around Germany, Austria, Czech Republic, and "Benelux" (Belgium and Netherlands really). I qualify for the Youth pass (saving about $200), but only if I use the pass at least ONCE within the first 5 days of my journey because after that I will be over 25.

Flights to Europe from Canada for me will be significantly cheapest ($200-300 less) if I fly into Paris or Rome. Neither of those cities will be part of my pass, however (I have read numerous times that the Eurail pass is not cost effective in Italy so I have left it off)

The final thing complicating my plan is I am really hoping to spend 3 weeks of June in Italy to try to beat the summer heat wave as much as I can.

So, I am wondering what would be the most efficient way for me to validate my pass within 5 days of arriving in Paris or Rome?

Some ides:
Paris --> Belgium --> fly to Rome as the start of my Italy leg
Rome --> Austria --> train or fly to Verona/Venice as the start of my Italy leg

Or, do I bite the bullet and roam Italy in the peak heat and tourist season of July?
Or, do you think it's too much of a hassle and I should just spend the extra $200 and get the pass later to use in July and August?
Or, should I spend ~$200 more and fly into Vienna instead?
Or maybe the Eurail pass isn't worth it for travelling 1 month between Brugges, Gent, Amsterdam, a city in Germany, Salzburg, Vienna and Prague...

Sorry for the headache!

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