Ten Fun Family Activities to Do in Boston for Labor Day Weekend

Boston is the “hot spot” – one of America’s greatest cities. People flock to Boston from across the country to embrace and absorb its history and beauty but, like anywhere, the residents of a city get used to its grandeur and tend to leave for vacation. Why not take a staycation this Labor Day weekend and enjoy all that Boston has to offer? Here are ten great ideas to kick off your weekend – whether it’s just you, your family, or a group of friends.

  1. Duck Boat cruise along Charles River – Boston is best seen by land and water, and the duck tour takes you from Boston Common to the Charles River on a single excursion, in a vintage, World War II amphibious vehicle.
  2. Boston Hop-on, Hop-off Trolley Tour – Explore the Cradle of Liberty with a hop-on hop-off bus pass. The route includes several stops at popular attractions and landmarks, including the historic North End and Boston Tea Party Ships.
  3. Martha’s Vineyard Daytrip – Your bus takes you from the city to the shore, where you take a ferry from Cape Cod. Enjoy the day soaking up the sea breeze and visiting this quaint island community which is home to the affluent and famous.
  4. Boston Whale Watching Cruise by High-Speed Catamaran – On this whale-watching tour, cruise out to the Stellwagen Bank National Marine Sanctuary in search of humpback and fin whales, as well as Atlantic white-sided dolphins. Learn about the wildlife from a naturalist guide.
  5. Tour of Historic Fenway Park – Take a guided tour of America’s oldest ballpark, home to the Boston Red Sox since 1912. Your guide shares commentary on Red Sox baseball legends and shows you iconic stadium features such as the green monster left field wall. If you’re in town for Labor Day weekend the Red Sox are hosting the Texas Rangers on Saturday and Sunday.
  6. Boston Freedom Trail Walking Tour – Walk the Freedom Trail with a guide in historic costume on a tour from Boston Common to Faneuil Hall, a 1.2-mile route that covers important sites in the heart of Boston.
  7. Boston Food and History North End Tour – First-time visitors and Boston regulars alike shouldn’t miss the chance to get to know the food, history, and culture of Boston on this tour.
  8. Boston Harbor Sightseeing Cruise Aboard a Classic Tall Ship – Explore Boston on the Liberty Clipper. Depending on the wind direction, you can see Fort Independence, or the Charlestown Navy Yard, home to the USS Constitution, as well as other historical sites.
  9. Harvard University Campus Guided Walking Tour – Explore one of the country’s best college campuses led by a student guide. Enjoy unique and personal insights into life at Ivy League institution “Hahvahd”, while learning about the school’s history as you tour the historical buildings, monuments, and outdoor spaces.
  10. Boston Signature Dinner Cruise – Plan a night out on the water for a sunset cruise which offers an all-you-can-eat dinner buffet, a beautiful view of the city from Boston Harbor, and live entertainment with dancing.


Regardless of which activity you choose, enjoy it. After all, Labor Day is all about celebrating America’s workforce – and that’s you!