Unlike the others on here, I found Amsterdam very drab and boring everytime I went to be quite honest. With that said, I spend 2 weeks last May in Europe, similar to what you're doing and had a great time. My girlfriend at the time had a 4 day long soccer tournament in Prague, so we decided to make the best of it and turned it into a 2 week long vacation in the area. The trip consisted of the following cities (in order with they were visited)
Frankfurt, Germany - Cheapest flight to the area at that time was to Frankfurt, so we decided to start and end our trip there. We spent 3 days here and actually liked it quite a bit. Popular opinion says that Frankfurt is kind of a boring city with not much to do. We didn't experience that. It was lively, extremely clean and fun. For some reason, I always imagine that if Calgary was in Europe, it would look exactly like Frankfurt.
Dresden, Germany - 4 hour train ride from Frankfurt and on the way to Prague. Maybe one of the most overlooked locations in Europe. I'm actually not sure why this place isn't very well known. It is basically everything you would imagine a renaissance European city to look like. It is very historic and very cultural. Maybe one of my favourite parts of the trip.
Prague, Czech Republic - 1.5 train ride from Dresden. Awesome night life. Very cheap everything and just a very fun city. The weather in early May though was more confused than May in Calgary. One day it was 28 degrees and humid, then I woke up the next morning and it was 6 degrees, windy and rainy. It made for a miserable last 2 days we spent there.
Brno, Czech Republic - Czech Republic's second largest city. 2 hour train ride from Prague. It is actually very similar to Prague, but smaller and way less tourists. It was nice, but not much to do there. I would maybe skip this place and go straight Vienna next time.
Salzburg, Austria - 3 hour train ride from Brno. Spent only a day here, but wish I spent more time there. The city is absolutely beautiful. It's a small, modern Austrian city right in the middle of the Austrian Alps.
Munich, Germany - 1.5 hour train ride from Salzburg. There is a special kind of big city buzz in Munich. It's always alive, always happening. There's always something to do in Munich. Probably my favourite part of the trip. The pubs are incredible, the people are very friendly and the architecture is awesome.
We then rented a vehicle, drove around Bavaria and back to Frankfurt to catch our flight to Calgary.
My recommendation is focus on one area of Europe and try to do a circle route and back out. I know a lot of travellers want to see everything all at once, but you truly can't enjoy the places you visit unless you spend some quality time there. Try to find the hidden gems like I found with Dresden. But above all else, enjoy your time and take it easy.
Let me know if you have any questions.
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