Discovering the Best of Historic Boston: A Weekend Itinerary

The United States looks to Boston for much of its history and heritage, and there’s a good chance many visitors to Massachusetts will do just that. But there’s a lot to see and do in one of America’s top tourist destinations, so plan on booking at least a long weekend to make sure you don’t miss seeing the best. Together with the travel experts at HotelsCombined, we’ve discovered some of the most fascinating destinations in this historic city.

Boston is about the size of Washington DC or the music-industry mecca of Nashville, so consider booking a hotel or other accommodations that are centrally located. Much of it is walkable in the downtown area, with adequate subway and public transportation options, but visitors may wish to rent a car if they’re planning a day trip to Cape Cod or inland historic sites dating back to the American Revolution. The city is easy to get to and served by both Amtrak’s high-speed Acela line and Logan International.

The North End: A Historic Starting Point

Once visitors have checked in, where to next? It’s hard to argue with the attractions of the city’s North End as a starting point. It’s home to the famous Old North Church, built in 1723, and the most-visited site in the city. The American Revolution began here with Paul Revere’s famous ride, and the church has continued operation since. There are affordable 30-minute “Behind The Scenes” tours offered every day, allowing guests to climb the bell tower and explore the tombs built beneath the church building.

Exploring Boston's Waterfront and Beyond

The green space of the Paul Revere Mall connects the church with Hanover Street, where visitors can easily navigate the few blocks east to the waterfront wharves, the New England Aquarium, and the Urban Arboretum. It’s just over a mile from the church to the Boston Tea Party Ships and Museum.

The Freedom Trail: A Walk Through History

Head north on Boston’s Freedom Trail, and across the Charlestown Bridge to the USS Constitution and adjacent maritime history museum. The Freedom Trail connects 16 historic sites, including Faneuil Hall and Boston Common. There’s even a Freedom Trail app to help locate the tombstones of the famous first patriots of the nation, like John Hancock and Benjamin Franklin’s family, who are buried there.

Boston's Universities and Museums

Boston is a working city, but it’s also a learned city with Harvard University and Massachusetts Institute of Technology just across the Charles River in Cambridge. Besides strolling the gardens on campus, you can check to see who’s on tap for a guest lecture or performing arts event and work it into your plans. Across the city at the University of Massachusetts is the John F. Kennedy Presidential Library and Museum.

Fenway Park and Boston's Sports Scene

Baseball fans know Fenway Park as a city landmark, and depending on the season, your travel plans may include taking in a Boston Red Sox home game. Fenway was built in 1912 and is the oldest Major League Baseball park in the nation, and tours are available whether the team is playing at home or not. If the ballpark and adjacent sports bar nightlife don’t interest you – and if you lean more toward the arts – Boston’s Museum of Fine Arts is just to the south of the Brookline stadium. The city also offers an opera house, exceptional theater-district venues, and the jewel that is the Isabella Stewart Gardner Museum; the latter has a unique exhibition based on art stolen by thieves dressed as Boston police back in 1990.

Hidden Gems: Boston's Lighthouses and Museums

Boston is full of hidden jewels. Boston Light, on Little Brewster Island in the harbor, is a 300-year-old traditional lighthouse kept by Sally Snowman, the last remaining lighthouse keeper in America who still personally gives tours. The city’s heritage lends itself to foodies looking for ethnic delights, from Little Italy to Little Armenia, and from Portuguese to Korean dishes. 

Boston's Neighborhoods: Food, Nightlife, and More

Boston has plenty of nightlife and plenty of watering holes too, but some of the best finds are in Boston neighborhoods. If your trip includes kids, you’ll want to get ice cream at Hood’s – it’s the giant 40-foot milk bottle at the Boston Children’s Museum. Little kids and big kids alike may also enjoy the Historic Franklin Park Zoo and its conservation mission.

Day Trips from Boston: Cape Cod and Beyond

Depending on how long the stay is, visitors may want to take a day or two and drive out to Cape Cod. A ferry will connect them to the Martha’s Vineyard and Nantucket islands; depending on your plans, you might even want to stay on the seashore and make your day trips into Boston or Providence instead! On the western end of the cape is the internationally famous Woods Hole Oceanographic Institute, which is open to the public for special events and, in summer, guided tours. Toward the Atlantic is the Cape Cod National Seashore, with nearly endless possibilities including whale and seal-watching tours in season.

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