Discover Boston’s best eats, quirky neighborhoods, and hidden gems. Walk the Freedom Trail, feast in the North End & explore the city Travel Brats style!
Boston is one of those cities that just gets under your skin in the best way possible. Equal parts old-school history and modern-day hustle, it’s where cobblestone streets meet glass skyscrapers, where the story of America was born, and where you can eat your body weight in lobster rolls without a shred of regret.
Founded in 1630 by English Puritans, Boston has played host to some of the most pivotal events in U.S. history—the Boston Tea Party, the Battle of Bunker Hill, and even the first public park in America. Today, it’s a vibrant mix of college-town energy, cutting-edge innovation, and diehard sports fandom (you’ll never hear a “Go Sox!” shouted with more passion than here).
I recently spent five days exploring Boston like a local, armed with a loose plan, comfy walking shoes, and an appetite big enough to conquer the city’s legendary food scene. Here’s how it all went down—my perfect Boston adventure.
Flying into Logan International Airport is a breeze—it’s practically right in the city. But here’s your first Boston pro-tip: skip renting a car if you can. Boston traffic is next-level chaotic, parking is expensive, and the city is surprisingly walkable. Between the subway (locals call it “the T”) and Uber, you’ll get around just fine.
Of course, I had to test the rental car waters—$368 for two days of a Nissan Rogue—and let me tell you, the line alone made me question my life choices. If you do rent, book with a company that lets you walk straight to the garage and grab your car. Otherwise, hop in an Uber and save yourself the headache.
I split my stay between two totally different vibes:
Around Copley, you’ll also find:
After a long travel day, we celebrated our first night with dinner at Lolita Cocina & Tequila Bar. Order the lobster guacamole and grilled elote—and when in Boston, remember the golden rule: always order seafood. Steaks are for later. Oh, and if you see Scrod on the menu? Don’t panic. It’s not a weird mythical fish; it’s just the white catch of the day—usually cod or haddock.
If Boston had a greatest hits album, it would be the Freedom Trail—a 2.5-mile path that connects 16 historic sites and tells the story of America’s revolution. You can do it self-guided, join a regular tour, or go all out with an actor-led adventure (think Paul Revere cosplay).
Start with caffeine at Thinking Cup Coffee Bar, then wander into Boston Common, the oldest public park in America (1634). It’s massive, filled with monuments, and now home to the striking Embrace Memorial, honoring Martin Luther King Jr.
From there, the trail unfolds like a time machine:
By now, you’ll be starving. Enter Union Oyster House, America’s oldest continuously operating restaurant (since 1826). The JFK booth is a must-sit, and yes—you’re ordering a lobster roll.
Don’t miss the New England Holocaust Memorial—six glass towers etched with survivor stories, both sobering and moving.
Then, if you’re lucky enough to visit in season, cap off your night at Fenway Park. Whether it’s catching a Red Sox game, snagging early batting practice passes, or just soaking up the energy at Cask ’n Flagon across the street (hot tip: persistence pays when getting a table here), Fenway is pure Boston.
Start with breakfast at Quincy Market, the ultimate food hall. Then dive back into history:
From here, pop back into Quincy Market for another lobster roll (yes, it’s worth a second one).
Keep following the trail:
Boston’s North End is an Italian dreamland, so refuel at Mike’s Pastry with a giant cannoli. (Pro tip: get a few extra to-go. You’ll thank me later.)
End the night at Bell in Hand Tavern (1795), America’s oldest continuously operating tavern. It’s rowdy, it’s historic, and it’s the perfect spot for your nightcap.
If your legs aren’t jelly yet, tackle the Bunker Hill Monument. Climb the 294 steps for killer views of the city.
From there, wander over to the USS Constitution, aka “Old Ironsides,” the oldest commissioned warship afloat. The ship and museum are free and make for an epic history-meets-maritime adventure.
For a modern twist, hop in an Uber to the JFK Presidential Library & Museum—a sleek, inspiring deep dive into the Camelot era. Afterward, head to Sam Adams Brewery in Jamaica Plain. Tours start at $10, include tastings, and give you all the Boston beer vibes.
Boston weather can turn on a dime, so I saved indoor treasures for day five.
The MFA is massive, so choose wisely:
Our trip ended on the water, with a Boston Harbor sunset cruise. Even in the rain, the top deck views were worth it. There’s a buffet dinner, DJ, and plenty of space to dance—because no Boston trip is complete without one last celebration.
Boston is the kind of city that can be done in a weekend but deserves a week. It’s history you can touch, seafood you’ll crave long after, and neighborhoods that feel like they’ve been waiting just for you.
If you only had one day, I’d say walk the Freedom Trail—it’s Boston in a nutshell. But if you want to experience the city like a local? Take your time, eat the lobster rolls, get lost in the cobblestone streets, and maybe—just maybe—let Fenway turn you into a Red Sox fan for life.
Boston, you’re wicked awesome.