Boston is famous for its rich colonial history, but this contemporary city isn’t stuck in the past by any means. While it proudly celebrates its heritage, the Hub always has something new and exciting going on, from cutting-edge art installations to celebrated chefs opening new restaurants at a breakneck pace.
Here’s how to spend two days in Boston, though we know after a taste, you’ll be ready to come back for more.
Taj Boston. Credit: The Indian Hotels Company Limited
Day One
You’ll want to stay somewhere central to all the city’s attractions and the Forbes Travel Guide Four-Star Taj Boston, right across the street from the Public Garden in the Back Bay, is an ideal spot to call home for a couple of days. The historic property offers a luxurious place to lay your head at night, and within steps you can be shopping on trendy Newbury Street or relaxing in the park.
If you’re lucky enough to visit during spring or summer, your first stop should be to ride a Swan Boat on the lagoon in the Public Garden — it’s a charming, bucket-list-worthy attraction. If your trip happens to fall during the winter, strap on some ice skates and hit frozen Frog Pond in Boston Common, just across the street from the Garden.
No matter the season, you should follow The Freedom Trail, which starts in the city’s most famous green space and leads to 16 essential historic sites, including the Old North Church, the Paul Revere House and Faneuil Hall.
And if you’re still hungry after sampling the food vendors of Faneuil Hall Marketplace and Quincy Market, head to the North End, Boston’s Italian neighborhood, for your pick of even more delicious options.
Should you be in the mood for casual and fast, try Regina Pizzeria for some of the tastiest pies in town. More upscale and elegant, Mare Oyster Bar is popular for its lobster rolls, among other fresh seafood offerings. For dessert, pick up cannoli from Mike’s Pastry or Modern Pastry — the rival bakeries make equally rich treats.
Once refueled, stroll through the Rose Kennedy Greenway, an urban park filled with gardens, artwork, fountains and even a Boston-themed carousel, which kids will clamor to ride. After all, where else can you take a spin on a cod or whale?
Spend the afternoon along the waterfront, where you can visit the New England Aquarium, the Boston Children’s Museum or the Institute of Contemporary Art, depending on your interests.
L’Espalier. Credit: L’Espalier
For a taste of history, pop by The Boston Tea Party Ships & Museum. This unique space gives an interactive look at our country’s colonial past with replica ships and high-tech exhibits, as well as the quaint Abigail’s Tea Room, which provides stunning views of the water and city.
After an afternoon of exploration, you’ll probably want to head back to the Taj to refresh and change for an evening out. Enjoy a pre-dinner cocktail in The Bar, the hotel’s elegant lounge, before walking down Boylston Street for dinner at Four-Star L’Espalier. Specializing in French cuisine, this fine-dining restaurant is renowned for its carefully curated tasting menus. Put yourself in the chef’s eminently capable hands and prepare to enjoy seasonal fare, like butter-poached Maine lobster or grilled quail with semolina porridge.
After an exquisite meal, you’ll be more than ready to turn in for the night.
Day Two
Fully refreshed, you’ll be ready to dedicate today to digging deeper into the city’s rich museum scene, this time in the Fenway neighborhood. You’ll need at least a half day to explore the enormous Museum of Fine Arts, Boston, which houses nearly half a million objects, ranging from ancient Egyptian artifacts to modern-day artworks. First-time visitors should opt for the free guided tour to avoid being overwhelmed by the massive attraction.
When you need a break, have lunch in one of the onsite eateries — we’re partial to the New American Café, a casual eatery in a glass-enclosed courtyard.
Just a few minutes away by foot is the Isabella Stewart Gardner Museum, a gem of a gallery that shouldn’t be missed. (Tip: flash your Museum of Fine Arts ticket for a discount.) Built by the eccentric and wealthy Stewart in the early 1900s, the stunning Venetian palazzo is home to her impressive collection of art, including Titian’s Rape of Europa, Giotto’s Presentation of Christ Child in the Temple and John Singer Sargent’s El Jaleo. The museum is exactly as she left it — a request specifically stipulated in her will — and that includes the beautiful interior courtyard.
If the AL East-leading Red Sox are in town, taking in a game at iconic Fenway Park is definitely something you should do. But you can go on an excellent behind-the-scenes tour of America’s oldest Major League Baseball stadium any time of year.
When you’re ready to rest your weary feet, make the short trek from Fenway to Kenmore Square’s Hotel Commonwealth. Order up a craft cocktail at the Hawthorne bar (renowned for its creative bartenders), down a dozen fresh oysters at Island Creek Oyster Bar as an appetizer, and finish with dinner at Eastern Standard for an elegant ending to your two-day trip.
