3 Days in Boston

Over Spring Break in 2025, we spent 3 fun and exciting days in Boston. Here are some highlights (focused on walking, history, food and drink) and favorites from our recent trip to beautiful and historic Boston, Massachusetts.

• While my family was still asleep after a late train arrival from NYC the night before, I was up early and managed to knock out a couple hours of work. But I wasn’t at our Airbnb—I was tucked into a seat at Pavement Coffeehouse’s Berklee location (their Fenway spot is also worth checking out). There, I found myself among locals: students reading and typing away like me, and tradesmen grabbing breakfast and chatting before heading off to their jobs. The atmosphere sparked a wave of nostalgia from my college days at the University of Illinois in Champaign. A 90s playlist—featuring tracks like Sublime’s Santeria—made it feel like it was still 1996. And honestly? It felt good. More than good -- it felt comfortable.

• Boston may have the best coffee shops in the United States. That's a bold statement but given the fact that the city is teeming with colleges and universities, it shouldn't be surprising. At any place I visited, I had great coffee and enjoyed an inviting experience infused with the energy of youth.

• Historic Walk # 1. Boston is arguably the best walking city in the United States. It's compact layout, cobblestone streets, historic brick buildings, and abundance of monuments give it a distinctly European feel--more so than any other American city--while immersing you in layers of rich U.S. history at nearly every turn. On one day, we took part in a 2 hour and 30 minute freedom trail tour. During the tour, we followed the 2.5 mile red line marked freedom trail stopping at 16 different historic sites where we learned about the Boston Massacre, Paul Revere, Samuel Adams and the Sons of Liberty. We visited fascinating cemeteries and ended the tour in the charming North End neighborhood with its winding streets, small and charming Italian restaurants and arguably Bostons most famous site, the Paul Revere Statue with the Old North church in the background. The tour was terrific but the key takeaway is to walk as much as possible in Boston to soak up the history and the many parks and historic buildings throughout the city.

• Historic Walk # 2. Another day began with a stop and go walk from the Back Bay up Commonwealth Avenue with the stops (15 in total) dedicated to learning about the historical figures memorialized on this grand avenue. In addition to the monuments, this central walkway is flanked on both sides by rows of spectacular brownstones, making it one of the premier city walks in the United States. It ends at the Boston Public Garden which is a beautiful expanse of green space and features the golden domed state capital which offers terrific photo opportunities, particularly on a blue sky day.

• Historic Walk # 3. On another day, we made our way up to the Medford neighborhood by way of the T (Boston's subway system) to explore Tufts University and meet our friend and Tufts student, Lola, for lunch. We enjoyed exploring the charming streets and homes in the area and walked away impressed by the historic University buildings and the impressive campus. After a terrific lunch at Semolina, we hopped back onto the T and made our way to Harvard Square. We meandered through the quad and walked around, soaking up the history. Student led tour groups stood in front of the beautiful white granite and red brick buildings listening to their guides explain the historical context of the buildings before their eyes. With the gray skies from the early morning showers fading, we decided to use our legs (instead of the T) and made the hour long walk back to our Airbnb in the Back Bay. We were glad we made that decision as we passed through

  

  Cambridge and saw our 3rd University of the day, walking through the heart of the MIT campus. The last leg of our walking tour took us over the Harvard Bridge and across the beautiful Charles River. We were happy to view the buildings on both sides of the river, the rowing teams making use of the river below and the joggers and walkers making use of the paths around us.

• Food. While I didn't get into food so much in this post, Boston has so much terrific food, across every ethnicity you can imagine, that you really can't go wrong in this city. Seafood is ubiquitous throughout Boston and the North End Italian restaurants are good and unique, but you can pretty much just pick any type of cuisine and you'll probably be happy. We had a good fast casual Mediterranean lunch at Sufra near Fenway and a terrific brunch at Tatte that features interesting Mediterranean dishes like shakshuka and a unique twist on the classic egg in a hole with the eggs nestled within a Jerusalem style bagel topped with fresh vegetables. The Time Out Market is in a great location and has some terrific food options.

• Democracy Brewing is SO Boston, with old world European charm and decor,

  good food (including a terrific Spanish tapas style platter) and even better onsite produced beer that is only available in the brewery. What an awesome place! Trillium Brewery (next to Time Out market) near Fenway is another nice spot for terrific craft beer, located in a very modern (and nice) glass encased venue with plenty to see all around.

  

  
  

• The Isabella Stewart Gardner Museum is a spectacular place to appreciate both world-class art and the natural light that streams in from every angle. The indoor garden beneath the atrium—a lush mix of sculpture, flowers, and greenery—adds a colorful serene aspect of beauty to the experience. This museum was built from the ground up to make art an integral part of every detail, from the floors to the ceilings and everything in between. Every element of Isabella Stewart Gardner’s home was meticulously curated by her to reflect artistic expression. That includes the imported Italian arches supporting the upper floors, as well as the staircases, doorways, embroidered walls, paintings, chairs, dishes, ceiling panels, and light fixtures—you get the idea. Everything. If you're curious about the infamous 1990 theft of 13 artworks (valued at an estimated $500 million) from this museum, the four-part 2021 Netflix documentary This Is a Robbery tells the story in gripping detail.

• The New England Holocaust Memorial is near Faneuil Hall and is a few minutes walk from the Freedom Trail. I've been to many Holocaust Memorial sights in my travels and outside of visiting a concentration camp (Dachau near Munich), I've been most impacted by visiting this sight. The 6 glass towers, glass etched numbers, survivor stories and the steam vents coming from underneath the 6 towers are to the bone chilling.