Best 293 things to do in Brookline, MA

See Boston's historic neighborhoods by e-bike with immersive live audio

Watch the Boston skyline at twilight on a 2-hour tall ship sail

Trace the people and places that sparked Boston's Revolution

Discover Revolutionary stories at Boston’s landmark Freedom Trail sites

Freedom Trail discoveries designed for young walkers ages 6–12

Taste french fries and pairings on a Harvard Square walking tour

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

Private Boston Harbor yacht cruise for celebrations and relaxed time on the water

Celebrate aboard a spacious vessel with a ballroom, two bars, and crew support

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

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

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

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

Walk the North End and Boston Public Market with pizza, cannoli, and chowder tastings

Eat your way through Boston’s North End with pizza, fresh mozzarella, pasta, and cannoli

Choose your stops, pedal together, and play your own soundtrack downtown

Soak at your temperature with Boston skyline views and plane watching

Discover Colonial-era Lexington on a 90-minute guided trolley ride led by costumed historians.

Explore Colonial Lexington Through Mixed Reality

Paddle Lake Cochituate with a single kayak rental in Natick

Pedal across Lake Cochituate with 1–4 hour rental options

Rent a stand-up paddleboard for a calm paddle on Lake Cochituate