As someone who lived in Boston for 5 years, I would say that Gloucester is good, but you'll have more fun in Rockport, IMO. Gloucester has nice places to be by the ocean, but Rockport is a great place to window shop in the cute little seaside boutiques and have a nice bowl of clam "chowda" and maybe a lobster. There is a great restaurant all the way at the end of the main street in Rockport, before the jetty. I think it's called "The Lobster Trap" but it's been quite a few years since I've been there, so I can't say 100%.
In Boston you can visit "Castle Island", which is a gorgeous place to go for a walk and be right on the water. It's by the South End of Boston, and while part of the city, it feels like you're a million miles away. It's very peaceful.
Posted on Apr 13, 2008, 1:07 PM from IP address 22.214.171.124