Sailing in Westford, MA

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

Take the helm or relax aboard a historic wooden schooner

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

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

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

Sail Boston Harbor at sunset on an 80-foot schooner

Private sail for up to 6 guests beyond Marblehead Harbor

Take the helm and discover sailing aboard a traditional cutter ketch

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

Step ashore on quiet harbor islands while your captain waits

Private sailing with coastal views along Boston's North Shore

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

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

Make Salem Sound your private escape aboard a classic schooner

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

Sunset sailing aboard John Alden's racing yacht

Sail Boston Harbor at sunset on a classic schooner

A private sunset outing aboard a historic schooner

Sail Boston Harbor with stories, skyline views, and complimentary pastries