Best results for Sailing in Salem, MA

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

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

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

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

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

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

Sail Boston Harbor at sunset on an 80-foot schooner

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

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

Charter a classic yacht for a relaxed Salem sunset sail

A private classic-yacht sail along the North Shore

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