“Boston Strong” is more than a slogan for this Massachusetts town. It’s a fierce mentality that this city keeps on permanent display.
You can feel it in the centuries-old brownstones and hear it at any Beantown bar past midnight when the crowds start crooning “Sweet Caroline” (the anthem of Fenway, Boston’s beloved ballpark). Soak in the culture of this sometimes glitzy (and occasionally gritty) city with a three-day weekend on the town.
As always, check for travel restrictions and closures before planning your trip.
Friday: Stroll Through Revolutionary History
Spend your morning following in the footsteps of one of Boston’s original heroes, Paul Revere. The Freedom Trail includes the home of the legendary patriot and provides a 2.5-mile tour of many of the country’s most important historic sites. Plus, you’ll get a good feel for this surprisingly compact and walkable city.
First, stop at Bova’s in the North End. Order a few pastries to see why this 24-hour bakery has been in operation for 90-plus years.
Next, head north to the Boston Common Visitor Center to pick up a map. Follow the double brick lines permanently embedded into the sidewalk and start off on The Freedom Trail.
The path follows crooked streets, leading to 16 designated stops in total. Over the first few blocks, you’ll pass by the Granary Burying Ground with headstones dating back to 1660, the Old South Meeting House where fed-up colonists converged to protest the British tax on tea and the site of the Boston Massacre.
Continue back through the North End to Paul Revere’s House and the Old North Church where the silversmith embarked on his famous ride.
Cross over the North Washington Street Bridge to the Bunker Hill neighborhood and finish your tour at the USS Constitution, a stunning black and red battleship parked at the Charlestown Naval Yard.
Stop for lunch at Warren Tavern. The Charlestown institution has been serving stick-to-your-ribs pub food since the 1780s. Take a taxi back to your starting point and spend the late afternoon lazing on the lawn at Boston Common.
If you have tots in tow, they’ll love the bronze Make Way for Ducklings Statue and the Swan Boats, which operate April through the end of August. If in-season, take a 15-minute pleasure cruise around the Public Garden pond.
Cap off your historic day with dinner and drinks on posh Newbury Street. Home to Boston’s highest-end shopping areas, the street has exceptional bistros and bars. La Voile serves classic French fare alongside a killer wine list, while the Saltie Girl shakes up innovative cocktails to pair with local seafood
Saturday: Get a Feel for the City’s Eclectic Neighborhoods
After that long first day of walking, strong coffee is in order. With an outpost downtown, George Howell is an excellent choice. The small-batch shop roasts beans fresh every day. Sip your espresso beverage of choice on a half-mile walk through Boston’s Chinatown community, a journey that begins at the neighborhood’s green-and-gold gates.
Head to Hei La Moon at 10:30 a.m. sharp, right when they open, and you’re likely to get a table at the two-story dim sum hall.
Take a seat and watch the dining room transform into a delightfully overwhelming blend of smells, sounds and silver carts. Go ahead, have a few more plates than is strictly responsible. The gai lan, cheong fun and egg tarts shouldn’t be missed.
Walk off brunch in the Seaport District. An impressive contrast to yesterday’s 17th-century structures, this redeveloped neighborhood is all contemporary architecture and converted warehouses.
Depending on your crew, make time for the Institute of Contemporary Art (best for adults), Boston Children’s Museum (under 10) and the New England Aquarium (all ages, located right across the bridge). Get a light, late lunch at Lookout Rooftop and Bar for some of the city’s best water views.
Drive back to Boston Proper to the Beacon Hill neighborhood. In the evening, wrought iron lamps light the slender streets. Spend some time admiring the Victorian row houses in this largely residential area. Stop in for a pint at the original “Cheers” bar — it’s less touristy than you might imagine. Then stop in at 75 Chestnut, a cozy, neighborhood favorite serving classic American fare.
Those with energy to burn should hop in a taxi to Lansdowne Street. You’ll find good-time locals and live music streaming out the dozen-plus bars and clubs that line the street.
Sunday: Art, Culture and Cannolis
One of the original American hubs of art and culture, Boston is home to nearly 60 museums. But many consider a quirky private residence-turned-public gallery to be the city’s crown jewel.
But first: breakfast. Order one of the fabulous sandwiches on freshly made bread from Flour Bakery, a local chain that has a number of locations around the city. Then make your way to the Fenway-Kenmore area to visit the Isabella Stewart Gardner Museum.
Made slightly more famous by the 2021 streaming documentary This is a Robbery: The World’s Biggest Art Heist, the Isabella Stewart Gardner Museum occupies the former home of an eccentric philanthropist of the same name.
Built in the style of a Venetian palace, it’s a great setting for a very peaceful morning spent exploring more than 7,500 paintings and sculptures and enjoying the courtyard, which stays green all year thanks to a vaulted glass ceiling.
Turn your cultured morning into a philosophical afternoon by popping over the Charles River to Boston’s sister city of Cambridge, the stomping ground for some of the world’s brightest minds. Take yourself on a tour of the Harvard University campus, with stops at the Memorial Church and Harvard Yard.
Order lunch at Mr. Bartley’s Burgers in Harvard Square, a student favorite since 1960, before spending a few hours exploring the Square itself. Watch for engaging street performers and find quirky independent boutiques alongside big-name retailers.
When night falls, it’s back to the North End. No Boston trip is complete without an authentic Italian meal in one of the city’s most charming neighborhoods. The tiny Daily Catch only takes walk-ins, so be prepared for a well-worth-it wait. Once inside, the smell of sizzling garlic and seafood will whet your appetite for shellfish, squid and pasta, prepared Sicilian-style.
For dessert, settle the city’s long standing debate on the best Italian bakery: Mike’s or Modern Pastry? Get a cannoli from both and let your palate be the judge.
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