Best 279 things to do in Gloucester, MA

Private 4-hour sail from Marblehead Harbor for up to 6 guests

Private sailing with coastal views along Boston's North Shore

Discover Salem Woods through plants, fungi, folklore, and witchcraft

Fish for mackerel and bass on a captain’s choice half-day trip

Spend eight hours targeting haddock, pollock, and other bottom fish in Massachusetts waters.

Fish for striped bass on a 2.5-hour trip near the Merrimack River mouth

Spot whales and dolphins with expert narration on the Atlantic Ocean

Flow through low-impact yoga alongside playful baby fainting goats

Pet, brush, and feed treats to baby fainting goats

Hand-feed alpacas, learn about the herd, and capture farm photos

Unwind with a gentle outdoor yoga flow alongside grazing alpacas

Fish Jeffrey's Ledge for haddock, pollock, and other bottom feeders

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

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

Target Haddock and Pollack, With a Nearshore Backup Plan

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

Paddle the Hampton Seabrook Estuary and add a fishing adventure

Soak at your temperature with Boston skyline views and plane watching

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