things to do in Winthrop, MA

Explore Boston with a compact, stable scooter built for easy maneuvering

Trace the opening day of the American Revolution with a licensed guide

Explore Beacon Hill’s architecture, politics and social history on foot

Cruise Boston Harbor and enjoy a fall brunch buffet aboard Northern Lights

Hear live ghost stories on a 90-minute Boston Harbor night cruise

Ride Boston’s Emerald Necklace on a 15+ mile guided bike tour

Paddle Lake Cochituate together in a sit-on-top tandem kayak

Celebrate on the water with a ballroom, two bars, and dedicated crew

Walk Salem’s witch-trial sites and uncover its maritime past

Introduce the family to deep-sea fishing with crew support for every age

Trace 400 years of immigration through Boston’s historic North End

Rent a pedal-assist e-bike and cruise Boston hills with ease

Explore Lake Cochituate with a sailboat rental for family-oriented time on the water

Private event yacht with a ballroom, two bars, and dedicated crew support

Taste North End pizza and hear Freedom Trail stories, ending with cannoli

Follow 400 years of immigration through Boston's North End

Fish Gloucester’s banks with a seasoned captain and crew

Rent a 3-bike car rack for weekend trips and races

Photograph Boston’s Back Bay, Public Garden, and Beacon Hill with guided tips

Private Boston Harbor outings with a captain, cooler, and bathroom

Taste chocolate treats and uncover local stories in Harvard Square

Fish beyond the usual day-trip range with 30% fewer people on board

Freedom Trail discoveries designed for young walkers ages 6–12

Rent a Kona Dew city bike and cruise Boston at your own pace