Each year my fiancé and I try to visit at least one city that we've never been to before (back in March we went here). It's a great way to explore new places and I love the idea of discovering favorite spots across the country. On Labor Day Weekend we're heading to Portland with some friends and I seriously can't wait. Usually our vacations are pretty chill and lack any sort of structure or organization, so I'm ready to have a set list of all the places we want to hit. If you have any recommendations (food, shopping, or otherwise), I'd be much appreciative of any tips! P.S. Are you an organized traveler or do you prefer to just figure it out as you go along?