Hi, what do you all think? This is my first big trip to Europe. I have spent some time in Russia, and in Amsterdam for a long layover, so I'm trying to keep it simple this trip. I'll be heading back more as I have family that just recently moved over there, so what do you think of this trip for a first time?
August 3: Arrive in Milan, where I will spend the next week or so hanging out with my family who I haven't seen in a while and making a couple day trips here and there with them. I will leave the itinerary totally up to them and aren't concerned about what I do, since I'll just enjoy hanging out with them
August 9: My buddy arrives in Milan
August 10: Rome
Aug 11: Rome
Aug 12: Rome
Aug 13: Rome
Aug 14: Florence (I don't know much about Florence, what do you all think about it?)
Aug 15: Florence
Aug 16: Venice (We are only spending a day here because I hear it is very expensive, no overnight stay)
Aug 17: Munich
Aug 18: Munich/Berlin (what do you all think)
Aug 19: Berlin
Aug 20: Paris
Aug 21: Paris
Aug 22: Paris...get back to Milan somehow to fly out Aug 23 (plane or overnight train?)
Your itinerary seems very rushed, especially when you factor in travel times which can eat up entire days sometimes. You may want to consider dropping a city to spread your time out better, or spend more time exploring the cities of one country or two countries over a smaller area.
Also I'd recommend dropping Florence and spending more time in Berlin. But that's just me.
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If it were me, I would cut out one of the German cities, and stick with the other for the extra day.
I like the Italy itinerary, I wasn't a fan of Venice and you truly only need a solid day to see the touristy sites. Florence deserves two days for sure.
It all depends on what you want to see more. If you're sick of Italy, then drop Florence as Roaulduke said and spend another day or two in Berlin/Munich. You could personally do a day trip to Florence yourself during the 6 days or so that you have. I'm sure thats no more than a 3 hour train ride(although I'm not 100% sure).
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July 23 - Sept 13: Back in Europe! Off to Brest, France for a French language course. Schedule is open before August 7 and after August 28, suggestions?
I like your itineray ! But I think we have uninimity here because I too would suggest you drop one city, in order to spend at least two nights per city.
In my opinion, the less convenient place in your itinerary is Paris, too far outside your route. So despite the fact that I looooove it and been there twice for six weeks total, I would suggest you keep it for another time.
Oh and... welcome to travelpunk.com !
My trip to Europe in August
because I too would suggest you drop one city, in order to spend at least two nights per city. 
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