Water Activities in Gloucester, MA

Sip and take in Boston Harbor's golden-hour skyline

See Boston’s skyline light up from a lively tiki boat cruise

Fish beyond the usual day-trip range with 30% fewer people on board

Host large celebrations with a ballroom, two bars, and crew service

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

Private tiki cruise for celebrations on Boston Harbor

Celebrate on your own yacht with a flybridge jacuzzi and room to unwind

Private sailing with coastal views along Boston's North Shore

Celebrate on a private tiki boat cruise through Boston Harbor

Cruise and connect at an all-ages sober meeting on the water

Cruise the harbor for Sail Boston tall-ship views with narration

Spot whales and dolphins with expert narration on the Atlantic Ocean

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

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

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

Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail

Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

Battle New England sharks on light tackle

Sail a 1930 schooner past Salem Sound lighthouses

Build practical night-navigation skills aboard a 36-foot cruising sailboat

Unwind on the harbor with your own snacks and drinks

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

Private yacht cruise for front-row Tall Ships views, up to 22 guests

Pair autumn views from the water with hot cider and orchard donuts