Sailing in Marblehead, MA

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

Sail a 1930 schooner past Salem Sound lighthouses

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

Make Salem Sound your private escape aboard a classic schooner

Sail Boston Harbor at sunset on an 80-foot schooner

Private sail for up to 6 guests beyond Marblehead Harbor

Sunset sailing aboard John Alden's racing yacht

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

Take the helm or relax aboard a historic wooden schooner

Private sailing with coastal views along Boston's North Shore

A private classic-yacht sail along the North Shore

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

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

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

A private sunset outing aboard a historic schooner

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

Learn to design, build, and repair sails in a hands-on two-day class

Sail Boston Harbor and enjoy freshly shucked oysters onboard

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

Build sailing skills with a private instructor-led session

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

Charter a classic yacht for a relaxed Salem sunset sail

Reserve a traditional schooner for your celebration on Gloucester Harbor

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