Gloucester's proximity to Stellwagen Bank and Jeffreys Ledge—two nutrient-rich, raised areas on the ocean floor that are like banquet tables for whales—make it one of the best New England ports from which to depart on a whale watching voyage. There are several whale watching companies that offer frequent departures from Gloucester during the season when whales are feeding: typically mid-April through October. Both Cape Ann Whale Watch and 7 Seas Whale Watch guarantee whale sightings, which means if you don't spy a whale, you'll be offered free tickets for a future trip.
There's something about the light in Gloucester and this rocky peninsula's natural beauty that has beckoned to artists for nearly two centuries. Don't miss the chance to see artists at work and shop for their one-of-a-kind creations at Rocky Neck Art Colony, the oldest continually working art colony in America. Dozens of painters, photographers, potters, jewelry makers, and textile designers have studios clustered along this waterside strip of land.
You'd be remiss if you visited Gloucester and didn't eat fish, lobster, and other sea fare fresh out of the Atlantic. America's oldest fishing port still has active commercial boats that chase groundfish like haddock and cod, pelagic fish like tuna and New England's favorite crustaceans: lobsters. The Gloucester House, a fixture on Seven Seas Wharf since 1958, is a reliable place to satisfy your seafood cravings, from raw oysters to pan-seared tuna to lobster rolls, served either warm with butter or chilled with mayo and celery. Lobster pie, lobster carbonara, even lobster stuffed lobster—the menu is loaded with indulgences, and the service is warm and welcoming.
Maritime Gloucester is a multifaceted waterfront attraction: part museum, part aquarium, part working shipyard. It's your place to touch a sea star, learn about and observe Gloucester's fishing fleet, view multimedia exhibits and even set sail aboard the Schooner Ardelle: constructed almost completely from materials salvaged from another schooner.
The Pinky Schooner Ardelle is a 58 foot, 49 passenger sailing vessel built and captained by shipwright and USCG licensed captain Harold Burnham. Ardelle sails from the Maritime Gloucester docks during the months of May-October. Adrelle offers daily public sails, private charters, and they partner with Maritime Gloucester to offer educational programming over the summer.
Gloucester's swanky Beauport Hotel, which opened in 2016, is a bit out of character in this rough and tumble fishing town. But even if you don't stay overnight (the rooftop pool, whirlpool, and bar will sure make you want to in the summer), make a reservation for dinner. There are phenomenal water views at 1606 Restaurant & Bar, as well as creative cocktails and a menu that features predominantly steaks and seafood including raw bar selections. There's live music in the cozy bar every Wednesday and Thursday evening.
Another picturesque coastal state park is Halibut Point State Park in Rockport. From here, you can see destinations far off in the distance when the weather is clear, including the Isles of Shoals in New Hampshire and Mount Agamenticus in Maine. This state park isn’t ideal for swimming, but there are tide pools to explore, areas for a picnic on the rocks, and trails to hike on. You can also take a tour of the granite quarry.