Best 146 things to do in Gloucester, MA

Cruise Hampton Beach on a 4-hour whale watching trip with bar and food galley onboard

Fish for mackerel on a 4-hour morning cruise with a family-run crew

Customize a private fishing or whale watch charter on a 70–90 ft boat

Customize a private fishing charter for up to 6 people

Fish Hampton Beach inlets for striped bass or bluefish

Spend 4 hours striped bass fishing with extra time on the water

Fish all day with the crew on a 9-hour bottom fishing trip

Spend 5 hours bottom fishing with bait and tackle provided

Fish at night with a family-run crew, with rod and reel rental included

Walk Boston’s North End for pizza, beer stops, and Paul Revere history

Eat your way through Boston’s North End on a private guided tour

Eat your way through Boston’s North End with pizza, fresh mozzarella, pasta, and cannoli

Walk the North End and Boston Public Market with pizza, cannoli, and chowder tastings

Taste North End favorites and explore Boston Public Market on a private 3.5-hour walk

Walk Old City with a guide and visit 4 Philly bars in 2 hours 15 minutes

Private Lexington & Concord tour with Battle Green, Old North Bridge, and author sites

See Boston and Cambridge by private minivan with flexible photo stops

See Boston landmarks and walk historic Salem on a 7-hour private day trip

See Boston’s key sights and local flavors on a private 5.5-hour tour

See Boston and Cambridge highlights by minivan with optional photo stops

See Boston in a day with a private vehicle, local stories, and two meals included

Walk all 16 Freedom Trail stops with a private guide plus a detour through Little Italy

Tour Lexington, Concord, and Boston’s Freedom Trail with private pickup

Taste classic Boston eats while exploring Revolutionary and immigrant history