Best 279 things to do in Gloucester, MA

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

Explore Old City’s hidden Revolutionary stories over stops at four Philadelphia bars

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

Trace the Revolution’s opening days and Concord’s literary history on a private tour

Explore Boston and Cambridge history with private minivan transport

Explore Boston's history beyond downtown with a private guide

See Boston and Cambridge highlights by minivan with optional photo stops

See Boston in a day with a private vehicle, local stories, and two meals included

Walk Boston's revolutionary landmarks and historic Little Italy with a local historian

Trace Revolutionary history from Lexington and Concord back to Boston

Taste Boston classics while tracing the city's Revolutionary and immigrant past

Discover the histories, architecture, and campus legends of MIT and Harvard

Explore Boston’s history with kid-friendly games on a private 4-hour tour

Follow Paul Revere’s story from Boston’s streets to the harbor

See Boston landmarks, then explore Salem’s witch trials history with private pickup

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

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

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

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

Sail Boston Harbor on the Liberty Star tall ship in 1.5 hours

Sail Boston Harbor at sunset on a classic schooner

See Boston by bike on a guided 10–12 mile City View Tour

Ride from Boston to Cambridge’s Harvard, MIT and Charles River sights

Ride the Charles River paths on a family-friendly Boston bike tour