Salem is a really cute, walkable town with lots of restaurants, shops and history. It's home to the House of the Seven Gables, Derby Bookstore and Gulu Gulu Cafe. Sarah loves the Peabody Essex Museum. Bret loves Notch Brewing. We both like the campy witchy vibe.
Rockport is the quintessential New England coastal village. There are great concerts at Shalin Liu, lots of art galleries, and kayak rentals at the harbor. Get some ice cream and go for a stroll out to the pier out on Bear Skin Neck.
Ipswich is a cute little town with a great coffee shop (Zumi's), but the best part is Crane Beach. It's a long open ocean beach with some gorgeous walks in the dunes. Crane Estate is an amazing historic house with gorgeous gardens. Work up an appetite and go the the Clam Box or Woodman's for lunch.
Manchester by the Sea is a lovely little town with a few restaurants, shops and all the convenient stuff. it's also importantly home to Sarah's favorite bookstore, Manchester by the Book.