Gloucester and Rockport have several beautiful beaches, including Good Harbor Beach, Long Beach, and Front Beach. Enjoy a day of swimming, sunbathing, or taking a stroll along the shore.

Bearskin Neck is a quaint shopping district that features shops, art galleries, and restaurants. Browse for unique gifts and souvenirs, such as handmade jewelry, pottery, and paintings.

Gloucester is known as the whale watching capital of the east coast. Take a whale watching tour from the harbor to see humpback, fin, and minke whales.

Both towns are known for their thriving art scenes. Visit galleries such as the Rockport Art Association, the Cape Ann Museum, and the North Shore Arts Association to see local artwork

There are several lighthouses in the area, including the famous Thatcher Island Twin Lights. Take a tour of the lighthouses or simply admire them from afar.

Charter a fishing boat or go on a fishing tour from one of the local companies, such as Cape Ann Marina, Yankee Fleet, Gloucester Fishing Charters, or Cape Ann Sport Fishing.

Coastal live fire cooking. Lots of smoky flavors and so good. Get the grilled lobster and fries or the burger or both.

Fancy pizzas and cocktails. We went here the night Nick asked Matt to be his best man.

A great place to stop by during a stroll on bearskin neck. Super casual, roll up to the shack, and eat on the back deck (if you can find a seat)!

The best Italian food. Their specials menu is a whole additional menu!! Where we celebrated after selecting our venue.

Our favorite spot to grab coffee on a Sunday morning drive. The butter crunch donut is a must try.

Great place for an Italian sub + lunch or after dinner pastries.

The cutest little store to grab a cone.

One of our favorite places in Cape Ann. Think farm to table meets seafood. The menu rotates every night. Where we went after we first visited the Beauport!