Best results for Water Activities in Gloucester, MA

Look for whales on a cruise to Stellwagen Bank

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

Fish Gloucester’s banks with a seasoned captain and crew

Cruise to Stellwagen Bank on a narrated 3–4 hour whale watch

Sail historic harbor waters with maritime insights and optional hands-on sailing

Private schooner sailing with captain and crew included

Paddle Salem’s historic coast with guided stories and coastal views

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

Sail a 1930 schooner past Salem Sound lighthouses

Make Salem Sound your private escape aboard a classic schooner

Sunset sailing aboard John Alden's racing yacht

A private sunset outing aboard a historic schooner

Take the helm or relax aboard a historic wooden schooner

Sail Salem’s North Shore aboard a storied 1939 wooden schooner

Raise the sails and sip mimosas aboard a classic yacht on Salem Sound

Sail Salem Sound with Sunday Bloody Mary specials and hands-on sailing options

Private sail for up to 6 guests beyond Marblehead Harbor

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

Private sailing with coastal views along Boston's North Shore

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

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