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Europe Itinerary, Help!

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Hello, So we are two 21-22 year old's planning this trip to Europe in late July or early August. We will be staying with friends, family , hostels/hotels. Luckily we will get to stay in two resorts, one in Italy and one in Spain (which we have not chosen yet). We will be getting the eurail pass as means of transport.

So what are we interested in:
Culture filled towns/cities
Historical sites ( museums, architecture, world war 2 sites, castles, old churches romantic sites, unusual sites, etc) Any recommendations would be greatly appreciated!

We will fly into Frankfurt, Germany, where we will spend the night (no lodging selected yet). From Frankfurt we will travel to Amsterdam, where we plan to stay 3 nights(no lodging selected yet). From Amsterdam we will pass through Brussels to Paris . In Paris we plan to stay for at least 2 nights (no lodging selected yet). From Paris we will pass through Switzerland and Munich into Prague where we plan to stay 4 nights (no lodging selected yet) From Prague we plan to travel to Venice. Once in Italy we plan to stay 3 nights in Venice, 4 nights in Florence, pass through Sienna and spend 2 nights in Rome. From Rome we will travel to Monoco (4 nights) (we haven't decided on a specific place yet, Help!) We are from Hawaii so we want to see more than just a nice beach, more cultural, small town vibe =) Lastly we will end our trip in Spain where we will spend 4 nights in Barcelona, 3 nights Madrid, I would really like to pass through Basque Country (heritage reasons) even tho its out of the way.

So we know its an ambitious itinerary and don't want to spend all our time traveling so we plan to travel during the night as much as possible and would consider eliminating places "not as worthy".

Your Help would be greatly appreciated!
>Itinerary
>Lodging
>Attractions
>Eatery

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