Family Vacation in Cape Ann

Family Vacation in Cape Ann
If a family vacation in Cape Ann, Massachusetts is on the cards, be prepared for a charming encounter with a time gone by. Located about 30 miles northeast of Boston, it would not call for a great deal of time or effort to visit or vacation in this beautiful destination by the sea. Known as the “other bay,” Cape Ann is a rocky promontory along the northern tip of Massachusetts Bay.

Enchanting old time towns like Essex, Manchester-by-the-Sea, Gloucester and Rockport make up the Cape area. Your family vacation in Cape Ann will take you through these historic towns.

The town of Gloucester, with its 375 year old port and famous harbor would be as good a place as any to begin your family vacation in Cape Ann.

The Cape Ann Museum is a great place to acquaint your young ones with some hands on art, and the good news is that kids under 12 enter free.


Take to the Gloucester Maritime Trail to explore the area. The harbor front has plenty of sights to set the right tone for a family vacation in Cape Ann. This is where you get to go whale watching on your family travel to Cape Ann.

Enjoy the fabulous seafood and river cruises of the quaint town of Essex. A bit further on you come upon the scenic beauty of Manchester-by-the-Sea. It would certainly add to the excitement of a family vacation to Cape Ann if you were to take Scenic route 127 to get here. The scenery is stunning and it gets you straight to downtown.

Singing Beach is the major attraction here where you can have a great family day out.

Family Fun Destinations

Rockport, at the very tip of the promontory, has its share of heart-warming quaintness to offer. If you are an art-lover, here’s where you load up with irresistible artwork. However, driving around might be a bit of a bother due to the acute shortage of parking spaces.

Areas like Bearskin are mostly pedestrian in any case, and it would be a good idea to hop on a trolley for this part of your family vacation in Cape Ann. Beer lovers bewares! Rockport is a dry town. You can bring your own favorite alcoholic drink, but will be charged for the use of glasses if at a restaurant.

Known for its historic lighthouses, art galleries, seafood, beaches, and quaint historicity, a family vacation to Cape Ann should definitely be on your agenda if you’re anywhere near Boston.

From mid-June to beginning of September is when the crowds throng the Cape; but it is not as bad as Cape Cod. From September to end of October you have the spectacular fall foliage to inspire you. This is indeed a great time to consider a beach vacation to Cape Ann.

Search Best Family Beach Vacations and find the right Family Vacation Hotel for your trip!


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