Portland Maine has earned a huge reputation for three major things, a foodie paradise, craft beer everywhere, and being exceptionally dog friendly. All of these are well deserved and make for a great trip. What to do with Bowser Casco Bay Mail Boat The Casco Bay Mail boat is a great way to get out and see the water and islands in the bay and is very dog friendly. You need to buy a ticket for Fido and seating is a bit at a premium, so line up early.