48 Hours in Boston: History, Beer, and Live Music

Staying in Back Bay

We based ourselves in the Back Bay neighborhood, and I could not recommend it enough. It felt central without being overwhelming, and we loved how easy it was to get to the hop-on hop-off bus route, shops, and plenty of restaurants. Back Bay is full of charm, from brownstone-lined streets to the buzz of Newbury Street. It had that perfect mix of neighborhood vibe and city energy. Staying here made it easy to explore during the day and still feel like we had a cozy home base to come back to at night.

First Stop: Fenway Park

There’s nothing like catching a game at Fenway. The energy, the crowd, the smell of ballpark food—it’s a classic Boston experience you can’t skip. Even if you’re not a die-hard baseball fan, the atmosphere alone is worth it. We hit it out of the park (sorry not sorry for the terrible pun) by getting to go twice. How you may ask? Saturday’s afternoon game got rained out, so we got to come back for the second game of a doubleheader the next day. Honestly, I couldn’t have asked for a better option. We splurged on tickets and got seats in the Sam Adams Deck, because what’s more Boston than that? It's out in right field, so we had a great view and got to see the Green Monster in all its glory across the field. 

Pro tip: get there early enough to walk around the entire stadium and grab a drink to soak it all in.

Touring Boston by Bus (Yes, Really)

We debated whether the hop-on, hop-off bus was worth it and let me tell you, it was. In a city with so much history, this was hands-down the best value and the best way to see the highlights without feeling rushed. Paul Revere’s house, Acorn Street, the Freedom Trail, even the oldest bar in town (hello, Bell in Hand Tavern) gave us the perfect mix of sightseeing and flexibility. 

We picked our hotel based on access to the bus route so it was easy to walk to one of the landmarks and hop right on. Of course, we managed to miss a turn and added about a mile to our walk, but we eventually looped back to the starting point and caught the bus without a problem.

Breweries & Pints

Boston and beer go hand-in-hand, so of course we had to tour the Sam Adams Brewery. We did the “Beyond the Brewhouse” tour. The tasting at the end was a highlight, but what really stood out was how much history and storytelling they weave into the tour. The Jamaica Plains brewery had the best vibes and we wish we would’ve had more time to hang out but had to get back to Fenway for the makeup game! 

And while Sam Adams was a classic stop, the real surprise was Downeast Cider. It is local to Boston, unfiltered, and has that perfect balance of crisp and slightly sweet. I fell in love with it after the first sip. If you see it on tap while you are in town, order it. And if you find it in cans, stock up. This became my go-to drink of the trip.

And speaking of drinks, if you only hit one bar in Boston, make it The Bebop. This Irish pub has live music every night, hearty pub food, and the kind of vibe that makes you stay longer than you planned. We stumbled across it on our walk back to the hotel after the Red Sox game got rained out and it was the best find. We were able to warm up with a bowl of Guinness Stew and stayed for the live music and delicious drinks. We went once, loved it, and immediately went back the next night. Zero regrets.

A Walk Through History

Boston feels like an open-air museum. You can walk through centuries just by turning a corner. From Paul Revere’s house to strolling down Acorn Street (yes, the most photographed street in Boston), to wandering Newbury Street for shopping and people-watching, it was the perfect balance of old and new. 

One thing that really caught us off guard was just how fascinating it was to wander through the old cemeteries scattered across the city. Unlike the centuries-old feel you get in parts of Europe, American cities don’t always exude that sense of history, but exploring these historic burial grounds turned out to be one of the coolest ways to connect with Boston’s past. Our visit happened to be in the fall, so the changing leaves and crisp air added an extra layer of atmosphere and a hint of spookiness that made the experience even more memorable.

A Bookstore Worth the Stop

The one spot that almost tied The Bebop for best-in-show was Trident Books & Café. It is the kind of place you walk into and immediately want to linger. Rows of books, cozy corners, and a menu that makes it impossible to choose just one thing. We popped in so I could browse the stacks and Cody could get some caffeine and ended up staying longer than we planned. It is a must if you love the mix of browsing a bookstore while sipping something tasty. 

Since this trip, we have now tried to find a "Trident" in every city we visit. What's better than finding a cozy spot to hang out, plus you can grab a book as a souvenir, and you'll be able to transport back to this city every time you read it. 

Final Thoughts

Boston is one of those cities that knows how to pack a punch. In just a weekend, we managed to:

• See the city highlights on a hop-on, hop-off bus tour
• Sip our way through the Sam Adams Brewery 
• Catch a game at Fenway Park
• End the nights at The Bebop Irish Pub (twice, because once wasn’t enough) 
  
  

If you love history, sports, and live music, Boston is the perfect spot for a quick adventure. Just don’t be surprised if you leave already planning your next trip back.