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Summer road trip in Europe need help! (Prague, Vienna, Venice & Milan)

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My mom and I are trying to plan a vacation to Europe. Ideally we would like to fly into Prague, Czech Republic stay there 2-3 nights, then we plan on driving up to the southern boarder of Poland to visit and stay with family, then drive to Vienna, Austria stay there 2-3 nights, then drive to Venice, Italy stay there 2-3 night, and finally drive to Milan, Italy where we will stay for another 2-3 days and then fly back home to the US!

I was wondering and hoping if anyone had any input, recommendations, tips, experiences, etc. that can help us plan our trip. I've been looking around the forum and read that many people did like AutoEurope as their rental car provider and that is about it! I plan on doing some extensive searching and researching on where to stay, where to go, and what to do on our trip but I figured I would also ask around to see if anyone has ever been to these places and had any suggestions on where to stay (hotels), where to stop while on the road, restaurants, theaters, some random place you found that you loved... anything! I would really appreciate it. Thank You!

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