We have a couple of vacations planned in these cities!
Portland: will be staying in the city for a few days and then going out into the "country" (Skamania resort area) for a couple of days. We will have a rental car, prefer to keep drives 2 hours or less. What are must sees in both in the city and surrounding areas? Bonus if it's a National Park since we can get in free Do we need to bring rain gear for a July visit? Assume we'll need a hoodie for evenings. We are going to skip Seattle this round, and save that for a different trip.
Boston: Will be staying in the Copley Square area. No car, so will be relying on public transportation. Must sees? We will be seeing a show at the Huntington Theatre and on top of that will have about 2 whole days to explore.
Kids are 10 and are mildly interested in history now (Paul Revere's house?). They're not big fans of hiking (one of them has some physical limitations) but shorter easy hikes are good and we will make her do those since she is otherwise pretty inactive. They enjoy museums, shopping, cool parks, worthy zoos, etc. I don't know if it's worth walking around the Boston area college campuses but maybe? It looks to me like July/August weather is mild with highs in the low 80s...that sounds lovely to me but is it humid? If it's humid and 80s that will be "hot" to me so we'll pack dri-fit stuff.
DH and I are also both interested in exploring places that locals would frequent. Both of these areas are contenders for "where to move when we retire that won't be dead hot in 20 years".