Boston is where America was born — and it still walks like it: a red brick line leads you through the Revolution, tall ships rock in the harbor, and the country’s oldest park sits a block from its first public library. This guide gathers the best of the city, with the places and tours our readers love most.
Where America was born: the Freedom Trail
Follow the red line: the Freedom Trail walking tour strings together 16 landmarks in one unforgettable walk, the costumed-guide tour makes history come alive, and the 250th anniversary tour celebrates the year it all began. Cap it at the Bunker Hill Monument — 294 steps to the best free view in the city.
Parks, gardens and the river
Start at Boston Common, America’s oldest public park, drift into the swan boats of the Public Garden, and follow the Charles River Esplanade as the skyline turns gold. The Rose Kennedy Greenway — a highway turned into a garden — ties downtown to the harbor.
Beacon Hill and the palace of books
Beacon Hill is Boston’s most photographed historic district: gas lamps, brick townhouses and Acorn Street. A few blocks away, the Boston Public Library is a palace for the people — free for all, and worth an hour of wandering.
The harbor: tall ships, whales and sunsets
Sail it like it’s 1797 aboard the classic tall ship cruise, chase humpbacks on the whale watching cruise to Stellwagen Bank, and end the day with the harbor sunset sail as the skyline lights up.
Food: the North End and the Fish Pier
Boston eats Italian in the North End: the North End food tour covers pizza, pasta and pastries with a lifelong local. For seafood, the Boston seafood tour goes behind the scenes at the historic Fish Pier.
Day trips from Boston
The Salem high-speed ferry turns witch city into an easy morning; the Martha’s Vineyard day trip is the happiest island escape; and in fall, the New Hampshire foliage trip dresses the White Mountains in red and gold.
Planning your days? Our Boston itineraries — from one perfect day to five — map out the Trail, the harbor and the day trips hour by hour. And subscribe to the Happy City News newsletter for Boston’s best events, every week.
