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First trip to Europe -- overwhelmed!

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I am a 22 year old student from Canada, and have never travelled outside of North America. My boyfriend has never been out of NA either, and we would love to travel to Europe for 4 weeks this summer but have no idea where to start in our planning.

My top places to see are:

Florence, Venice, Rome
Amsterdam and/or Berlin

Is it too much of a stretch to include Santorini in there? It's the #1 place I want to go to, but I will definitely make more trips to Europe in the future, so it's not a total dealbreaker. My #2 place to go to is Italy.

What would be the best order to see these places and how should I travel in between?
Is it also feasible to keep this trip under 5000$ (each person)?

Thank you SO much for any help!!

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