things to do in Winthrop, MA

Paddle Salem Harbor your way with flexible kayak rentals

Cruise Boston Harbor with a gourmet brunch buffet and captain commentary

Taste your way through downtown Boston on a private donut walk

Taste seasonal donuts while tracing Boston’s holiday traditions from downtown to the North End

Private Boston and Salem history tour with Revolutionary and witch-hunt stories

Trace campus history, pranks, and architecture from MIT to Harvard Square

Pair an oceanfront castle with Salem's true 1692 story

Trace April 19, 1775 with a licensed guide, from Old North Church to Bunker Hill

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.

Reel in haddock and bring home your eligible catch

Chase giant bluefin tuna on a hands-on offshore fishing trip

Battle New England sharks on light tackle

Bottom fish for haddock with bait and tackle included

A private sunset outing aboard a historic schooner

Charter a classic yacht for a relaxed Salem sunset sail

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

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