Best results for Water Activities in Winthrop, MA

Host large celebrations with a ballroom, two bars, and crew service

Charter a private yacht and cruise Boston’s waterfront with your group

Charter a 50-foot yacht for your private Boston Harbor cruise

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 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

Paddle Salem Harbor at your own pace from Salem Willows Park

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

Paddle Salem Harbor your way with flexible kayak rentals

Paddle Salem’s coast at dusk with beginner-friendly guidance

Paddle Beverly Harbor and Salem Sound at your own pace

Explore Beverly Harbor and Salem Sound at your own pace

Build confidence on the water with personalized paddling instruction

Build paddling skills with private instruction tailored to your experience

Pedal the Charles River and explore Nahanton Park from the water

Paddle calm Charles River waters through Nahanton Park

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

Battle New England sharks on light tackle

Join the crew for hands-on giant bluefin tuna fishing

Paddle Lake Cochituate with a single kayak rental in Natick