Trips I'm Planning: Boston Itinerary

As an example of just how OCD I am, I think I have an *almost* complete idea of what to do while we're visiting Boston. Which isn't till October, by the way. I'll be going with Kellie, who hasn't been before, so I'm trying to come up with a combination of the slightly touristy stuff you need to do on your first trip to Boston and the fun, chill stuff I like to do because I love the city so much. And we're also trying to pack in some other random stuff, if we get around to it. Here are two versions that we're thinking about:

Itinerary 1:
Friday - arrive @ 7am - hotel
Friday morning - chill, Dunkin Donuts, nap, wander
Friday afternoon - possible Sam Adams tour (Kellie REALLY wants to go! Yeay beer!)
Saturday morning - Dunkin Donuts, take train to Salem
Saturday evening - chill, nap, wander, eat, drink
Sunday morning - ferry to Provincetown (Is there enough to see in/close to Provincetown? Can you rent bikes there? Does Provincetown give you a decent representation of Cape Cod?)
Sunday evening - chill, nap, wander
Monday morning - chill, wander, Dunkin Donuts, eat
Monday late morning - pick up rental car, drive to Providence, RI, then to CT

Itinerary 2:
Friday & Saturday the same, then...
Sunday - Dunkin Donuts, shopping, wandering, chill, drink, eat
Monday - EARLY AM - pick up rental car, drive to Cape Cod
Monday - Cape Cod

On the second one, we'd have to add another night - stay one night in Cape Cod instead of CT, and arrive on Thursday to Fredericksburg instead of Wednesday night. I guess we'll have to decide our priorities... I think we'd rather get to Fredericksburg earlier rather than later so we have more time to spend with Ashleigh. But we'll see! Thoughts?