Also for those of you that are curious about the first port - Portland, you're better googling Weymouth, that's the town the port is in.
I'm from the UK so I'll try and give you an idea of what to expect! It's what we call a "seaside town", so if you're wanting to try proper fish & chips this will be the place! There'll be plenty of places to grab a drink (think classic English pub) and there'll be loads English high street shops as well as loads of little shops with all kinds of bits and pieces.