Itineraries for Your Trip to Boston
1 Day in Boston for First Timers
As a kid who lived in the countryside of Massachusetts, I was always excited to visit family in the capital city. I still get teased for calling Boston’s skyscrapers “castles.” To be fair, the city’s European-inspired architecture is the closest thing Massachusetts has to castles, and its streets either feel alive with history or buzz with the youthful energy of a big college town.
It’s hard to get to know Boston in just one day, but if it's your first time there and you're short on time, start with these activities: discovering tidbits of American Revolution history and checking out the skyline from the water.
If you only have time for one thing, make it a meal at Faneuil Hall's indoor food market.
Expect hot and humid summers and mild shoulder seasons in Boston, but pack layers when visiting in the cold, windy winter.
Start your day in Boston by learning about the city’s significance during the American Revolution on a Freedom Trail walking tour. (There are also bus tours if you aren’t comfortable being on your feet for long.) Highlights include visiting the nearly 300-year-old Faneuil Hall Marketplace to browse food stalls and learn about Paul Revere’s legacy in the North End, passing by numerous monuments, statues, and historical sites.
In the afternoon, use Boston’s subway system (which locals call the "T”) to head to the Boston Harbor. There, stroll on the Harborwalk before hopping on a cruise to admire the skyline from the water as you pass by significant sites like the Bunker Hill Monument or the USS *Constitution* warship. If you’re in town between May and October, consider taking a whale-watching cruise instead and keep your eyes peeled for humpbacks, finbacks, and even right whales.
After a day’s sightseeing, admire Boston’s skyscrapers from the water on a sunset cruise. Choose a cruise that’s right for you. Perhaps stay in a historical mood with a trip on a 1920s-style yacht, or pull out the stops on a state-of-the-art motorboat cruise that includes a buffet dinner, live cabaret, and stellar views of Boston’s illuminated towers and bridges.
