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Help with Italy/Greece/Istanbul trip

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I am from the states and just got back from a trip to Switzerland. It was my first trip out of the country and the reason Switzerland was chosen is that my great, great grandfather on my dad's mother's side was from Grindelwald. (We also went to Austria but that was just because it was too convenient not to soak that in as well).

"The bug has bitten" - The trip was amazing and I want to plan another trip next summer (because we need time to save up money). The trip would be myself and my girlfriend. We would probably have to limit the trip length to 2 weeks max, maybe less. My top choices are Italy and Greece. I also am very fascinated with Instanbul.

**Here is my ideal plan,** - I am posting here because I don't know if it is realistic, and even if it is, I don't know what things I would need to consider when planning:

We would fly in to Italy (which airport would depend on flight prices). We would spend roughly 2 long days in Rome, 1-2 days in Venice, and 1-2 days in Genoa or Milan. We would have rail passes and take trains between the cities. We would then fly to Athens and spend 2-3 days there, then take a train to Thessaloniki or somewhere else that is towards Turkey. Then we would take another train to Istanbul and spend 2-3 days there before flying home to the states from Istanbul.

Our budget will probably be around $7,000 USD. That is for flights and hotel and everything. We would spend roughly a combined $1,500 on 'regional' travel. I can get our from and to USA flights for about $1,000 USD per person round trip. That leaves about $3,500 USD for let's say roughly 12 days and 11 nights of hotel, travel, food, and expenses. That is roughly $291 per day which (I would hope) to be like $120 hotel, $100 food/drinks, $70 on sight-seeing admission etc. per day which hopefully would be enough to be comfortable as well as see/do enough stuff to make it an unforgettable trip. We are both frugal and indulgent at the same time i.e. we are careful enough of what we spend on our money that we can consistently 'splurge' as well.

Is the route efficient?
Are there better places to consider?
Is the trip length reasonable?
Are the prices within reason?
Even if all "yes" what are the major considerations?
What languages should we learn, if only conversational?
What pitfalls do we need to ensure we avoid?
And any links to helpful information/stories/advice would be greatly appreciated as well!

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