Sailing in Gloucester, MA

Take the helm or relax aboard a historic wooden schooner

Make the day your own with island hopping, lighthouse views and a swim

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

Shape your own sailing adventure, with the option to swim

Private sail for up to 6 guests beyond Marblehead Harbor

Take in Boston's waterfront with harbor history or music on a leisurely private sail

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

Private sailing with coastal views along Boston's North Shore

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

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.

Sail a 1930 schooner past Salem Sound lighthouses

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

Take in Boston's waterfront from a sailboat reserved for your group

Weekend brunch sail on Boston Harbor with pastries, coffee, and tea

Hands-on 1812-style sail with engaging crew and scenic Salem Sound views

Make Salem Sound your private escape aboard a classic schooner

Reserve a traditional schooner for your celebration on Gloucester Harbor

Sail Boston Harbor at sunset on an 80-foot schooner

Take the helm and discover sailing aboard a traditional cutter ketch

Private schooner sailing with captain and crew included

Sail Boston Harbor and enjoy freshly shucked oysters onboard

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

Sunset sailing aboard John Alden's racing yacht