My First Trip to Boston
…. livin’ my life on Boston time
A Perfect First Day in Boston
To celebrate my boyfriend’s birthday, we decided to take a weekend trip to Boston, a city full of history and charm that neither of us had been to.
Our adventure began as we hopped off the plane and onto the train, making our way to The Liberty hotel in Beacon Hill. We were ready to explore.
The hotel, which was a former jail, (I share more below) in a quick 8ish minute walk from the subway, steps away from Charles Street, and 12-15 minutes from Boston Common and Boston Public Garden, and about 20 minutes from Chinatown.
Other luxury hotels I recommend in Boston (in no particular order):
The Langham Boston
Mandarin Oriental Boston
Four Seasons Hotel Boston
To make your trip to Boston even more amazing, book your hotel using this link. You’ll receive VIP amenities, upgrades, and other exclusive offers.
After settling in, we headed to explore the North End. It’s a charming neighborhood with narrow streets and old-world vibes—plus a lot of laundromats? Neither of us really like Italian food that much so we were looking for seafood.
My friend Megan recommended we stop at Pauli’s for the quintessential Boston eats—hot lobster and clam chowdah—which were even more delicious than they sounded.
After eating a lot of food, we wandered over to Paul Revere Mall and rented a blue bike to ride along the waterfront while visiting the USS Constitution.
Usually, I don’t purchase anything that requires me to download an app, but I thought, what the heck, “YOLO,” as they say. It took me all of 2 minutes to download the app, and it cost maybe $2. It was a blast.
I love riding bikes in new cities to explore.
Returning to the North End, we stumbled upon a random carnival I loved. My favorite part was probably the poodle working one of the games.
Soon, it was time to head to Roadrunner, an epic venue, for New Found Glory’s 20th. Catalyst concert. Their energy was AMAZING. I love hitting concerts in new cities—it’s like a mini adventure within an adventure.
There’s something so exciting about stepping into a venue in a place I’ve never been. It’s not just about the music; it’s about soaking up the local culture and vibe, feeling the crowd's energy, and seeing how different places experience the same band.
It was funny to hear “HOW ARE YOU DOING BOSTON!?!” instead of “Kansas City!” but I loved it. The venue was absolutely incredible and I’ll be seeing what other shows will be heading their way just to experience it again.
And it was a perfect start to the weekend.
Once we got back to The Liberty, we took some time to explore the different parts of the hotel that used to be a jail.
The historic Suffolk County Jail was vacated in 1991 when its inmates were moved to a new facility, which was acquired by Massachusetts General Hospital in 1991; the property was carefully redeveloped into a hotel while preserving its significant architectural elements.
Their restaurants pay homage to the old jail, Click, and Alibi, which both serve incredible food and bring in patrons from the city to enjoy the iconic hotel.
A Lovely Second Day in Boston
The next day, we decided to take a lovely stroll down Charles Street, one of the most charming streets in Boston. Lined with super cute boutiques, antique shops, and cozy cafes, Charles Street perfectly blends old and new.
We found ourselves at the Boston Public Garden just a short walk from Charles Street. America’s first public botanical garden is a beautiful escape in the city's heart. I laid in the park for while John watched football on his phone and if that’s not the definition of romance, I don’t know what is.
After enjoying the Swan boats, we headed to Cambridge for a tour of Harvard.
There’s something truly inspiring about walking around one of the oldest and most prestigious universities in the world. Let’s just say I didn’t feel smart.
We took our time wandering through Harvard Yard, surrounded by historic buildings and the beautiful, tree-lined paths that make the campus feel like another planet.
It was easy to get caught up in imagining all the great minds that had walked these same paths. We stopped by the famous John Harvard statue for a quick photo—because I’m not above being a cheesy tourist. I touched his gold toe for good luck. There’s 3 things wrong with that statue - you’ll have to find out for yourself when you visit!
We walked to what is now my favorite restaurant in the world - Alive & Kicking in Cambridge, a no-frills spot known for its fresh seafood. We were on a mission to try their legendary lobster sandwiches, and they did not disappoint. Wowwowow.
The food was delicious—simple, fresh, and exactly what we needed to refuel for the rest of our day. I’m still thinking about it.
Because we were on a vacation, we decided to get another meal at The Barking Crab, a super fun spot on the waterfront. The sun was setting, and ate oysters, enjoying the fun signs all over the restaurant.
To cap off the day, we strolled to the Boston Tea Party marker, which perfectly showcases Boston’s rich history. Walking along the harbor felt a little surreal. To be honest, I’m still confused about the entire event but that’s on me.
The next day, we woke up feeling excited to dive back into exploring more of Boston. We started our morning with a visit to Fenway Park, a must-see for any first-time visitor to the city.
Walking into Fenway was felt so historical? It’s hard to describe. The Green Monster did not disappoint. The vibe around the game was so fun and John got EPIC seats in the sun so I was happy. I can totally see how it’s one of America’s most beloved ballparks.
We even witnessed a homerun from the Peske Pole - later John signed it.
From there, we made our way to Chinatown for. I LOVE CHINATOWN.
The streets were super vibrant and filled with all sorts of smells. It was hard to choose where to eat, mostly because I wasn’t that hungry after eating a hot dog at Fenway, but that’s beside the point.
We ended up at a little dumpling shop - and had a few bites to eat before walking back through Boston Public Garden, Boston Commons, and Charles Street.
The Last Day in Boston :(
Our last day in Boston just so happened to be John's birthday, and he kicked it off in the best way possible—by ordering us the most amazing omelets for breakfast. He went for the corned beef omelet, and oh my goodness… it was so good.
Mouth = watering as we speak. I don’t know how he found this place but it was probably the best non-seafood thing I ate the whole trip.
Fueled by those incredible omelets, we decided to take a final stroll around the city and soak in as much as possible before heading home to Kansas City. We first walked over to the Boston Public Market, a great spot with local vendors selling everything from fresh produce to artisan cheeses and baked goods. I got a green smoothie.
From there, we made our way to Quincy Market. We loved the people watching.
Before heading back to the airport, we decided to walk a portion of the Freedom Trail. We’d covered a lot of ground in Boston over the past few days, but there’s always something new to see on the trail. Even with the little time we had left, we made it a point to visit Paul Revere’s house.
Leaving Boston was bittersweet, but I couldn’t have asked for a better way to celebrate John's birthday. I felt so grateful for all of the adventures and can’t wait to come back and visit another time soon!
