Luggage and bags: A beach bag in the summertime, or a satchel with an extra layer of clothing when boating (see below).
If you go to the beach, be prepared for trash problems. This summer, the City of Gloucester is experimenting with a 'carry-in/carry-out program' whereby they stopped placing trash receptacles at the beaches. Hypothetically, this is supposed to condition beachgoers into taking their trash back to their cars with them. It might help slightly if the City were to put dumpsters at the beach entrances, but they've taken the new measures to the extreme. So, bring trash bags to the beach with you, or else you won't have any place to put your food wrappers, diapers, travel trash, etc.
Clothing/Shoes/Weather Gear: Weather has become increasingly unpredictable in Gloucester. The best recommendation is to dress in layers and mix and match accordingly, especially aboard a whale watching boat where it's chilly even in the summertime. There are enough chain drug stores and supermarkets near the beach that you don't have to worry about cheap sunglasses, suntan lotion, etc. Bring dressy clothes only if you're attending a wedding.
Toiletries and Medical Supplies: Readily accessible; see above.
Photo Equipment: The chain drug stores develop photos quickly, but there is a camera store right in Main Street Plaza called Photographics for more sophisticated needs.
Camping/Beach/Outdoor Gear: There are campgrounds in West Gloucester. The best known beaches are Wingaersheek in West Gloucester and Good Harbor Beach in East Gloucester. Check with the Cape Ann Chamber of Commerce at (978) 283-1601 for more details. Warning: Parking is expensive and in short supply at the beaches!
Miscellaneous: Mosquito season starts around mid-July. Plan accordingly or you'll get eaten alive, especially in East Gloucester near the water.
Luggage and bags: BACK PACK'S WILL GIVE YOU MOBILITY..
Clothing/Shoes/Weather Gear: Walking shoes shorts,sunscreen,sun glasses. pack a sweater or lite jacket, the ocean can get cool even in the summer.
Photo Equipment: Gloucester is photo frendly, we have 4 photo shops as well as cvs, walgreens you can get real one hour service an tec support for digital.
Miscellaneous: This is a fantastic place to walk and site see.Old homes and the city has a walking tour route the has old coast guard bouy that tell you whats here and what you can do