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From Reykjavik to Madrid… I need advice!

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So I am in the middle of planning a whirlwind tour of Europe later this August.

So far here is the itinerary:

US>Reykjvaik
Reykjvaik>Oslo
Oslo>Dublin/Wicklow
Dublin>Amsterdam
Amsterdam>Berlin
Berlin>Prague
Prague>Santorini
Santorini>Rome>Venice
Venice>Bern
Bern>Paris
Paris>Madrid

The budget is $4500-$5000 for everything (transportation/hostels/food/sightseeing/nightlife)

I've already secured airline/hostels from the leg of the trip that goes from reykjavik to dublin so that part of the trip is planned. I'm struggling with the most inexpensive way to do the rest of the trip. I'm NOT buying a rail pass. I plan to do a mixture of flying and trains. Any advice on when to book plane tickets? Best places to fly into/out of? Any suggestions for alternative routes that might save money (For example: Prague>Budapest>Santorini (not staying in Budapest but perhaps this alt route is less expensive, etc.).

Help!!

Thank you!

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