things to do in South Boston, MA

Explore Hammond Castle and Salem’s 1690s history on a semi-private guided day trip

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

Sail Salem Sound with your group of up to 40 and enjoy a private, hands-on experience

Immerse yourself in Boston's Freedom Trail chronicle with a small-group, storyteller-led walk.

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

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

Reserve a traditional schooner for your celebration on Gloucester Harbor

Private schooner sailing with captain and crew included

Sail into the sunset with live Celtic tunes and sea shanties

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

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

Crew an authentic WWII tank destroyer and feel the power on a short ride course

Drive a 1944 M4A3 Sherman with 1-on-1 instruction and time for photos

Climb aboard a 1944 M24 Chaffee tank for a 10-minute group ride

Climb aboard a 1944 M4A3 Sherman for a 10-minute ride for two