Boston: Where History Meets Chowder

There’s something about walking through history that makes it come alive—and few places capture the spirit of America’s past quite like Boston, Massachusetts. As a history lover, I couldn’t wait to explore the city where so many defining moments of our nation took place. We hopped on a train from NYC for a long weekend escape, arriving just in time for the hustle and bustle of Boston University’s move-in weekend—which made the city buzz with excitement.

Our Stay

We stayed at the most charming bed and breakfast...okay, technically it's Jeff’s great uncle’s home and honestly, that made it extra meaningful. It's located just around the corner from Boston University. The house was full of character and warmth, and every morning we were greeted by the soft sounds of classics like Frank Sinatra drifting through the air—music to my old soul.

Jeff’s uncle, a retired chef and Cuban cookbook author, treated us to unforgettable meals, and the cozy backyard patio—complete with an outdoor bar—set the perfect tone for slow mornings and relaxed evenings. It was the kind of stay that made the trip feel extra special from the start.

Exploring the Best of Boston

Walking around Boston felt like stepping onto the set of a history movie—except with coffee shops on every corner. Every block has a story, and I’m sure we unknowingly strolled past dozens of important spots. But here are a few of the ones that stood out:

The Freedom Trail – This is Boston’s ultimate highlight reel. The red-brick path winds you past 16 historic landmarks, so even if you’re not a history buff, you’ll feel like one by the end. It’s basically a “no-FOMO” way of sightseeing.

Massachusetts State House – With its glittering golden dome, it’s hard to miss. First opened in 1798, it still houses the state’s government. Imagine clocking in every day at a place tourists line up to photograph. 

Park Street Church – Built in 1809, this 217-foot steeple once dominated Boston's skyline and was the very first landmark travelers saw as they approached the city. 

Old City Hall – A French Revival building that has watched Boston reinvent itself over and over. It’s the kind of place you half-expect to see powdered wigs walking in and out.

Boston Massacre Site – Marked by a medallion right along the Freedom Trail, this is where things got heated between colonists and redcoats. At certain times you can catch a full reenactment, which makes history feel way less textbook-y and a lot more real (and dramatic).

Paul Revere House – Paul Revere’s “Midnight Ride” might be legendary, but standing inside his home makes it feel even more personal. Touring his house felt like peeking behind the curtain of a myth—he wasn’t just a rider shouting “The British are coming!”; he was a real person with a real life (and charmingly simple house).

Fenway Park – The “Green Monster” is iconic. Even without a game, it felt electric seeing it in person. One day, we have to come back during baseball season—it just feels wrong not to.

USS Constitution – Also known as “Old Ironsides,” this ship is the real deal. Launched in 1797, it’s still officially part of the U.S. Navy, and the crew even fires cannons twice a day. It's free to board, but if you're tall, consider it a built-in obstacle course - watch your head! Me? I walked around carefree—short people win this round!

Harvard University – We visited on move-in day, which meant the campus was buzzing with nervous freshmen and proud parents. The brick buildings, the energy, the sense of history—it was all amazing. And yes, I may have whispered “What, like it’s hard?” a few times (shoutout to Legally Blonde).

Calories Don't Count on Vacation

One of the best perks of staying with a chef - besides the great company - is, of course, the food! Every morning started with a fresh, gourmet breakfast that made us feel completely spoiled. One evening, the hospitality expanded even further when extended family and friends gathered for a backyard BBQ. Between the delicious food and the lively conversation, it was the perfect way to spend an evening in Boston. 

Pier 6 - When Jeff's uncle wanted to show us more of the city, he treated us to lunch on the water at Pier 6. It's also where he once hosted a cookbook signing event, which made it feel even more special. With ocean breezes, gorgeous views, and a menu that comes highly recommended by a chef himself, it was a memorable meal in every way. 

Top of the Hub (closed in 2020) - For a night out, we enjoyed a date at the iconic Top of the Hub, perched at the top of the Prudential Center. While the restaurant has since closed, the experience was unforgettable. If you visit Boston now, you can still head to the observation deck nearby for those same sweeping city views.

From iconic landmarks like the Paul Revere House and Fenway Park to hidden gems along the harbor, Boston is a city that offers something for everyone. Whether you’re a history buff, a foodie, or just someone who loves exploring walkable cities, Boston delivers. We can’t wait to return and dive even deeper into everything this incredible city has to offer. Until next time Boston - save us a seat at Fenway and a bowl of clam chowder.