things to do in Chestnut Hill, MA

Sail Boston Harbor at sunset for views of the tall ships and skyline lights

Ride Boston’s waterfront and neighborhoods with a Harpoon Brewery stop

See 3D Salem and Halloween exhibits year-round

Give your birthday celebration a creative, hands-on twist

Pedal across Lake Cochituate with 1–4 hour rental options

Paddle Lake Cochituate in a stable canoe built for easy exploration

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

Build sailing skills with a private instructor-led session

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

Interact with a wide range of animals on a private, keeper-led experience

Trace Boston’s rock, punk, jazz, and folk roots with a local musician

Make local flavors part of your pre-game ritual

Discover Boston’s hidden history beyond the Revolutionary era

Bring your dog aboard for harbor views and light evening narration

Ride alongside Scrooge for a playful take on a holiday classic

Explore spirit-making with an optional 3-sample tasting

Eat your way through Boston’s North End on a private guided tour

A sweet Harvard Square stroll with donut treats and a beverage pairing

Taste North End favorites and explore Boston Public Market on a private 3.5-hour walk

Taste local flavors and discover Cambridge murals on a social evening out

Walk downtown Salem with a kid-focused guide and hear true Witch Trials stories

Paddle Lake Massapoag together in a stable sit-on-top kayak

Paddle Lake Massapoag at your own pace

Paddle Lake Massapoag at your own pace in a single kayak