Water Activities in Winthrop, MA

Private tiki cruise for celebrations on Boston Harbor

Private sailing with coastal views along Boston's North Shore

Celebrate on a private tiki boat cruise through Boston Harbor

Cruise the harbor for Sail Boston tall-ship views with narration

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

Paddle Salem’s historic coast with guided stories and coastal views

Cruise Boston Harbor with a gourmet brunch buffet and captain commentary

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

Reel in haddock and bring home your eligible catch

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

Pedal the Charles River and explore Nahanton Park from the water

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

Paddle Salem Harbor your way with flexible kayak rentals

Private yacht cruise for front-row Tall Ships views, up to 22 guests

Reserve a traditional schooner for your celebration on Gloucester Harbor

Build sailing skills with a private instructor-led session

Sail Boston Harbor and enjoy freshly shucked oysters onboard

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

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

Charter a classic yacht for a relaxed Salem sunset sail

Bring your dog aboard for harbor views and light evening narration

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