Water Activities in Gloucester, MA

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

Sail into the sunset with live Celtic tunes and sea shanties

Experience a calm private winter paddle with dry suits and an expert guide on sheltered New England waters

Cruise Boston Harbor on a 1.5-hour narrated history tour

End the day with sunset views from an island vantage point

Step ashore on quiet harbor islands while your captain waits

A private sunset outing aboard a historic schooner

Cast for striped bass on an all-ages fishing outing

Watch the Boston skyline at twilight on a 2-hour tall ship sail

Enjoy a light-tackle fishing trip that works well for kids and adults

Cruise Boston Harbor on a private yacht for Tall Ships views

Private water time with your playlist and room to celebrate

Fish Hampton Beach inlets for striped bass or bluefish

See visiting schooners up close during Gloucester's Heritage Day celebration

Paddle Salem’s coast at dusk with beginner-friendly guidance

Cruise Boston Harbor at sunset and watch the USS Constitution cannon fire

Reach farther-off fishing spots without sacrificing fishing time

Bring your dog aboard for harbor views and light evening narration

Charter a classic yacht for a relaxed Salem sunset sail

A full day on the water targeting whiting and ling

Sail Boston Harbor on the Liberty Star tall ship in 1.5 hours

Introduce the family to deep-sea fishing with crew support for every age

Watch fireworks from the water on a Wednesday-night cruise

A private classic-yacht sail along the North Shore