Boston, MA
After a fantastic couple of days exploring Providence (and somehow clocking nearly 15,000 steps a day), we boarded a quick and easy train ride to Boston - legs sore, but spirits high. There’s something magical about arriving in a new city by train; we watched the scenery shift from quiet New England charm to the bustling energy of a historic metropolis. We checked into the hotel, dropped off our luggage and headed out to explore the city.
Sunday Evening: Hangry in the North End
Our first mission was simple: find food. We made our way straight to Boston’s iconic North End, expecting to dive right into a warm bowl of pasta or a hot slice of pizza. What we didn’t expect was the mob of people who had the exact same plan. Every restaurant we passed had a 2+ hour wait or was reservation only. Even the casual pizza joints had lines wrapped around the block. Our group was quickly approaching “hangry” status. After some aimless (and slightly desperate) wandering, a few of us decided to retreat to the hotel restaurant & bar just to get something to eat. Thankfully, a few of us scored a quick win: to-go clam chowder from the Sail Loft. With their dine-in reservations booked out for months, this felt like a small miracle. We sat on benches over looking the harbor with steaming cups of chowder, soaking in the salty air and the comfort of Boston’s signature dish - exactly what we needed to tide us over until dinner.
Re-energized, we wandered back through the North End’s historic streets. We passed Paul Revere’s home and stood outside the Old North Church - the site of the famed lantern signal, “One if by land, two if by sea.” It was surreal to be walking the same cobblestone paths where the earliest sparks of the American Revolution were lit.
Much later that evening, after the crowds had thinned and our feet had logged even more steps, we finally found a small pizza spot with no line. It was nothing fancy, just a couple of pipping hot pizzas shared among the group, but at that moment, it was all we could ask for.
Monday: Quincy, Fenway & Row 34
After a much needed slow morning, our group of seven slowly rallied and made our way to Quincy Market for lunch. This bustling food hall housed under a landmark colonnade offers stalls and bays serving everything from lobster rolls to naan wraps. Ryan and I kept it simple and went for clam chowder (in a bread bowl!) and peel-and-eat shrimp from the Boston and Maine Fish Co.’s stall. The chowder was creamy and loaded with chucks of tender potatoes and clumps of soft clam. The shrimp were plump and juicy and paired with a tasty cocktail sauce. It still amazes me how Boston does seafood so effortlessly.
After filling up, we hopped on the MBTA green line and rode just a few stops over to the Museum of Fine Arts. To our delight Memorial Day Weekend meant free tickets, but our excitement quickly turned to disappointment when we saw the line snaking around the building and down several city blocks. It was a bummer, particularly because they currently have not one but two Van Gogh exhibits on display. However, we didn’t want to spend our only full day in Boston waiting in line in the hot sun.
Since the MFA was a no-go, we redirected our stroll through Memorial park towards the Fenway/Kenmore area. With an hour to kill before our Fenway Stadium tour, we swung into Cisco Brewers for a round of their locally brewed beers and hard seltzers on the patio. The cold, crisp, flavorful brews were a welcomed pick-me-up from the heat, and Ryan was so impressed that he bought the t-shirt.
When it came time for our Fenway tour, our guide Vic immediately stole the show. You could tell that he lived and breathed Red Sox lore - he was a walking encyclopedia of baseball trivia. We learned about the imposing “Green Monster” in left field, the infamous curse of the Bambino, and even saw the single “home run red seat” marking the longest homerun ever hit at Fenway. They even had the shinny World Series trophies out for us to see and take photos with. Finally, the tour ended with a quintessential Fenway frank - another nod to our group’s reoccurring hot-dog habit.
After our tour we headed north to Beacon Hill. Strolling through Boston Commons, we followed winding paths under towering elms and tracked down the infamous bench from Good Will Hunting nestled under a leafy canopy. Beacon Hill’s brick sidewalks and gas-lit lanterns beckoned us towards cool boutiques and antique shops. We window shopped and even pop into some antique stores to browse. Eventually, we pause at a bar on Charles Street for a quick cocktail on the patio to soak in the evening glow before making our way back to the hotel to freshen up for dinner.
Our group headed to Row 34 in the Seaport district, where sleek modern design meets waterfront views. We kicked things off with multiple rounds of east coat oysters. I ordered the crab cakes and I’d rank them among the best I’ve tasted (second to only T’s of course). Laughter and chatter filled the long table as we shared stores and life advice among friends.
Tuesday: Lattes, Lobster & a Little Revolution
Ryan and I snuck out early Tuesday morning to explore more of the Seaport area before the group woke up. Our destination: Lakon French Patisserie. I had seen their tiramisu latte all over Instagram and needed to try it for myself. It was just as good as advertised—creamy, espresso-rich, with a subtle hint of cocoa. Paired with a buttery croissant, it was the perfect start to our last morning. We then wandered through the Seaport’s shopping mall and summer pop-up stores, browsing boutique shops and admiring waterfront art installations, before rendezvousing with everyone else for lunch.
The Barking Crab sits on a floating deck right over the water—mismatched picnic tables, crab traps stacked in corners, and that unmistakable “down-home” seafood aroma. Naturally, we ordered more clam chowder and more peel-and-eat shrimp. Halfway through our seafood boil, we joked that maybe, just maybe, we were becoming official “clam chowder connoisseurs.”
After lunch, we headed across the harbor to the Boston Tea Party Ships & Museum. It was delightfully over-the-top, with actors in period garb giving dramatic speeches. We were each given a name and character description of a real life person who attended the rebellion and asked to play along. The guide explained the stakes, and with a theatrical “three, two, one,” we hurled our “crates of tea” into the harbor. While a bit cheesy, the experience wrapped with a powerful short film that reminded us of how that single act sparked a revolution. The film laid out the sacrifices colonists made in the months that followed: boycotts, reprisals, and ultimately war. It was a sobering reminder of the bravery and conviction that sparked the birth of a nation. A fitting way to close out our time in this history-drenched city.
Before heading to the airport, we made one last stop at the rooftop bar at The Envoy Hotel. With sweeping views of the skyline and harbor, we clinked glasses in the late afternoon sun - grateful for good food, great memories and the best travel crew we could ask for.
We boarded our flight home late that night, exhausted but smiling. Our feet may never forgive us, but our hearts were full - and our stomachs, most definitely, were full of clam chowder. Already dreaming of our return. Maybe next time we’ll actually make it inside the MFA.
All is well,
H