Adventures in Sweets

I recently returned to Boston following a weekend at Cape Cod. It is a city steeped in history and, simultaneously, one that continues to evolve. I also appreciate its walkability and the convenience of the subway (known as the “T”). As with any major city, Boston offers plenty of things to do, but if you only have 48 hours, here is how I would spend it.

Day One – Boston Common, Freedom Trail, North End

For breakfast, I recommend the Thinking Cup near Boston Common. Thinking Cup serves the West Coast favorite, Stumptown Coffee, and has a variety of sweet and savory breakfast options to start the day. Eat in their cozy cafe or take it to go across the street into America’s oldest park, Boston Common. Continue your morning stroll through Boston Common to the Boston Public Garden to see if you can spot the “Make Way for Ducks” sculpture or the bench made famous by Robin Williams in Good Will Hunting.

From there, circle back to the Boston Common Visitor Information Center and the start of the Freedom Trail. The Freedom Trail is a 2.5-mile trail that takes visitors to 16 major historical sites throughout Boston, including the site of the Boston Massacre, Paul Revere’s House, the Old State House, Faneuil Hall, and the Old North Church. It can be a self-guided tour by following the brick path in the sidewalk or you can opt for a tour led by a costumed guide focused on your particular area of interest.

For lunch, there are many options at Faneuil Hall and the Boston Public Market, both of which are located along the Freedom Trail. They can be crowded, so I recommend Monica’s Mercato in the North End. There may be a line out the door, but the sandwiches are some of the best in the city. One sandwich can easily satisfy two people (maybe even three!) and can be enjoyed a few blocks away at the Paul Revere Mall, near the Old North Church. For dessert, grab one of the famous cannolis at Mike’s Pastry (again, one is probably enough for two people!) – of note, they are cash only!

After all the walking (hello, 10,000 steps), this would be a good time to head back to your hotel to grab a nap and regroup for dinner. Boston has an incredible food scene with a plethora of options. I’d recommend the Fox & the Knife from Top Chef alum, Karen Akunowicz. Her Italian-inspired menu has a variety of shareable plates, including our favorites: the fried chili chickpeas, Taleggio stuffed focaccia, and mafaldini alla funghi. If you have a smaller party, make reservations for the Chef’s Counter for an up-close look at the open kitchen.

Day Two – Newbury Street, Boston Public Library, Fenway Park

I love a good bookstore, so start the day at Trident Booksellers & Cafe for a hearty sit-down breakfast followed by a perusal of the latest bestsellers. Continue window shopping (or actual shopping!) down Boston’s most famous shopping thoroughfare, Newbury Street. If you happen to be there on a summer Sunday, it will be closed to car traffic and many shops will set up booths right on the street creating an outdoor market vibe.

When you reach Dartmouth Street, hang a right and two blocks down you will find yourself greeted by the statues representing Art and Science in front of the Boston Public Library, the first large free municipal library in the United States. A booklet with the major points of interest can be picked up in the lobby and serve as your guide through the library. Free guided tours are available and are on a first-come, first-serve basis. Refer to their website for the current schedule.

From the Copley Square rail station, hop on the T to Fenway Park or the Museum of Fine Arts. For sports fans, Fenway Park is one of the most iconic, historic baseball stadiums. It is worth catching a game if the Red Sox are in town. Otherwise, book a tour for a behind-the-scenes look at this legendary ballpark. After the tour, swing by Sweet Cheeks Q by Top Chef and Food Network regular, Tiffani Faison, for some of the best barbecue in Boston. The biscuits are out of this world and pair perfectly with the pork belly.

For those who prefer fine art to the art of sport, the Museum of Fine Arts has nearly 500,000 works in 21 galleries and an impressive rotation of special exhibits. With so much to see, a free MFA gallery tour is offered daily to help orient you. During inclement weather, the Museum of Fine Arts is a great way to spend a few hours.

When you’re ready for dinner, head to the most famous seafood establishment in Boston, Legal Seafoods. In 2024, it was voted the Best Clam Chowder in Boston and serves up some of the most delicious seafood in town. If you are not in the mood for seafood, consult Boston Magazine’s Best Of Dining guide for more mouthwatering options. As you sit down to eat, order a Sam Adams beer, and cheers to your Boston memories!