Jacob,
I'm not all that familiar with Portland but have some friends who've spent a lot of time there so I'll try to get you some info soon. There are certainly great places to visit in Portland (the old port, specifically) and a whole lot more within easy driving distance: two examples would be Portsmouth, NH about an hour to the South and Acadia National Park a bit over an hour further up the coast. If you do swing down towards Portsmouth I'll give you my contact info, that's where I work 5+ days a week. I should also be able to give you some off the beaten path beaches to visit as well if you want to chill out during the day time. Good seafood won't be hard to come by.