Sailing in East Boston, MA

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

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

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

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

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

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

Reserve a traditional schooner for your celebration on Gloucester Harbor

Private schooner sailing with captain and crew included

Shape your own sailing adventure, with the option to swim

Sail Boston Harbor at sunset on an 80-foot schooner

Sunset sailing aboard John Alden's racing yacht

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

Sail Boston Harbor and enjoy freshly shucked oysters onboard

Take the helm and discover sailing aboard a traditional cutter ketch

Step ashore on quiet harbor islands while your captain waits