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2 Weeks in Sept - Munich, Milan, Paris? Suggestions please!

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My girlfriend and I are planning a 2 week-ish trip to Europe in late Sept. We are meeting some friends in Munich to kick off the trip with some Oktoberfest fun so that piece of the trip isn't flexible, this is planned for 9/24-9/27. From there we would like to visit two other places, we're limiting it because we're aware that travel days can be long and tiring so 3 total locations seems reasonable.

So here is where we need help! Would seeing Milan and then Paris (then fly home from Paris) be good picks? I've been to the UK before but she's never been to Europe at all. We're kind of into seeing Italy but don't want to visit more than one place there and then Paris is kind of a go-to spot for our first Euro trip. We are open to any other suggestions of course and any decent hotel suggestions in each place would be great - looking for safe, decent quality hotels in convenient tourist locations. Budget is kind of flexible but figure in the $200-300 range per night, if one destination is more spendy we can tick that up.

Also need suggestions on the best way to book trips these days. Should we use travel deal sites? Look for all-inclusive types of trips(this could alter our destinations of course), or are travel agents the more affordable option now? All advice welcome, thanks!

Some other spots we're into: Prague, Barcelona, other parts of Germany or Italy.

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