
The landmarks in every guidebook — and the tours that tell you what guidebooks don't.
Boston was founded in 1630 by Puritan settlers on a peninsula they called Shawmut, and it has been trading on its history ever since -- which is appropriate, since the history is genuinely remarkable. The Freedom Trail, a 2.5-mile red line painted on the city's sidewalks, connects 16 sites from Boston Common to the Bunker Hill Monument in Charlestown: the 1713 Old State House, Faneuil Hall where patriots argued the case for revolution, the Old North Church where lanterns hung on the night of April 18, 1775. The trail is the most efficient walking tour in America, compressing 400 years into an afternoon that keeps surprising you.
The North End, Boston's oldest residential neighborhood, became the Italian-American quarter in the early 20th century and has held its character: summer festival weekends fill Hanover Street with saints' processions and cannoli lines that wrap around the block.
Fenway Park, built in 1912 and still the smallest ballpark in the major leagues, sits inside a residential neighborhood in a way that makes no planning sense and works completely. The Charles River Esplanade on a spring morning, with Harvard rowers on the water and the skyline behind them, is one of those places where the city doesn't attempt to explain itself but simply lets you look. For its physical size, Boston packs in more history, more universities, and more strongly-held opinions than almost any comparable city on earth.

Before you walk.
All 50+ languages, included with every booking.
Unlock every Boston tour — plus thousands more worldwide. Cancel any time.

4.8 across the App Store and Google Play. Here's a few we keep coming back to.
This tour was such a great way to see the city. The stories were interesting without feeling too scripted, and I loved being able to explore at my own pace.
This was a solid way to get to know Brighton without feeling like a tourist. The narration had depth and context, but didn't overdo it.
Started this tour with a croissant in one hand and zero expectations. The app just vibes with you, no pressure, just you, your headphones, and some cool stories.