Perfect Day on Massachusetts' Cape Ann

This quaint seaside town is proud of its Italian and Portuguese heritage as well as its fisherman roots. There are numerous galleries and shops along Main Street, parallel to the harbor.

For a real Gloucester lunch, go to Virgilio's shop at the end of main street. This Italian staple serves not just sandwiches and pizzas but also a whole lot of character and historical charm.

Head over to Good Harbor, located just two miles from the town's center, for fine sand and great views of the picturesque coastline.

Historic seaside town with plenty of shops, galleries and restaurants. For a scenic walk, head over to the Halibut Point State Park, about 2 miles North of the town center.

Located in the seaside town of Essex, you can delight in the traditional seafood fare of New England at the spot where the fried clam was invented. Great spot for families.

If you're looking for relaxed evening entertainment, the Franklin is the place. Stylish, dimly lit establishment on Main Street, serving haute cuisine and smooth Jazz.

Still not ready to retire? Head across the street to the White Rainbow Restaurant for delicious Martinis.