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Originally Posted by Medusa
The only piece of advice that hasn't been touched on yet is to compromise on the way you visit the cities. Take some time to wander aimlessly, it's a great way to find non-typical touristy things...but plan to see something in each city that you really want to see. I hate having my trips planned out completely, but I always make sure that I set some time aside to do things that I really want to do.
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I think that will be the most challenging thing for us to overcome. My girlfriend is a planner and I'm not so much. I love getting lost and just wandering around aimlessly, but she gets anxious when she gets lost.
-Tamerlain