Best results for Sailing in Gloucester, MA

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

Private schooner sailing with captain and crew included

Sail into the sunset with live Celtic tunes and sea shanties

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

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

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

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

Sail Boston Harbor at sunset on a classic schooner

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

Sail Boston Harbor at sunset on an 80-foot schooner

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

Photograph visiting schooners as they arrive for Gloucester’s festival weekend

Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

Charter a classic yacht for a relaxed Salem sunset sail