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Starting to ballpark estimate 3-4 week trip

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Hey there Fodor people,
I know this type of thing gets done frequently but I figured you could impart some wisdom. I am just starting to spur of the moment look into a 3-4 week trip backpacking mid February to mid March. I want to absorb one country and make a little getaway to a second. So like 20 days in Spain and 5 in a city in Italy with a nice day trip. I am. 24 year old thrill seeker who is looking to do this pretty close to the lower end of backpacker budgets including couch surfing if necessary. I will however splurge for a few Michelin starred meals and some vineyard sightseeing if possible. I know this is broad but a little about my interests, I enjoy museums history art food wine beer outdoors hiking culture in general. I am sometimes looking to spend as minimal money on certain days in foreign countries (for instance hiking a mountain or visit an old Viking settlement)
I'd appreciate any help you can give me, and this would include a flight round trip from Boston to Madrid/Venice/Barcelona wherever was most convenient

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