Take advantage of Gloucester’s seaport status and explore the New England Atlantic coast. There are several fishing charter ships that will take passengers out for some deep-sea fishing. Amanda Marie Fishing Charters offers full and half-day trips for shark, tuna, haddock, cod, bass or a variety of other species, depending on the season. Atlantic Yankee is another company that has similar offers, only they do overnight trips and whale watching expeditions as well. Kayman Charters fishes all winter long, but offers most of its trips during the warmer months. They also have “twilight delight” specials for fishing on Saturday evenings. You should expect to spend a few hundred dollars total for a half-day trip, and a thousand or more for a full-day trip, so bring some friends to split the cost.

If you'd prefer to just relax and enjoy the water, why not go for a sail? Check out Defiance Sail Charters, owned and operated by Lisa Kennedy and Raffi Kassabian. Spend a few hours, a day, or even multiple days aboard Windfall, a 49-foot Hinckley ketch. They are based in Smith's Cove at Beacon Marine Basin, within walking distance to the famed artist colony of Rocky Neck.

Cape Ann also has some great beaches and parks. Harbor, Half Moon, Wingaersheek, Niles, Old Garden, Long and Pebble Beach are all in Gloucester or Rockport, and more or less accessible by the bus. You can also use the commuter rail to go to Manchester-by-the-Sea or Essex, which have nice coastlines as well. Halibut Point State Park is located at the northern tip of the island, and there are a few other smaller parks like Dogtown, Ravenswood and Stage Fort in the area that offer good places for hiking, birdwatching or picnicking.