How to Spend 2 Days in Boston
With two days in Boston, you have time for both a generous dose of American revolutionary history and to explore its more modern side. From charting the origins of US independence on its historical Freedom Trail to taking a whale-watching cruise, here are some ways to spend a perfect 48 hours in the city.
Day 1: Exploring the City
Morning: Boston has plenty to fill your first morning. Follow the Freedom Trail to sites including Faneuil Hall and the 18th-century USS Constitution warship, or explore Harvard University or the city’s museums. Walking and bike tours cover the top sights, or buy a discount sightseeing pass or hop-on hop-off ticket for more flexibility.
Afternoon: After a morning of sightseeing, dial up the adventure for the afternoon. Splash down into the waters of the Charles River on a Boston Duck amphibious tour, or if it’s whale-watching season (generally April-October), take to a high-speed catamaran to see whales in nearby Massachusetts Bay.
Night: Revolutionary history infuses every corner of Boston, making it especially atmospheric after dark. Explore the city’s secret lanes and spooky legends on a ghost-themed evening tour. Options include guided walks into Boston’s oldest lamp-lit districts and a trolley tour that takes you to the city’s haunted buildings and half-forgotten graveyards.
Day 2: Freedom and Food Trails
Morning: Delve into Boston’s revolutionary war heritage on its Freedom Trail. Take a walking tour along the redbrick trail to learn about its British colonial and patriot past, or see the sights from a private car. Finish at the Tea Party Ships and Museum in Boston Harbor to learn more about the war-sparking protests.
Afternoon: See a different side of the city on a tour of some of Boston’s culinary hot spots. Join a guided food walk around the city’s North End district—aka “Little Italy”— to taste its pizzas. Alternatively, opt for a tour of Beacon Hill to discover off-the-beaten path eateries and treats that many miss.
Night: At dusk, take a harbor cruise to relax after your sightseeing and watch the sunset from the water. Choose an all-singing, all-dancing boat with a dinner buffet and live entertainment, or opt for a mellower cruise that settles for serving up sundowner cocktails alongside the city views.