Planning a trip to Boston? I’ve put together 15 of my favorite places to visit—from can't-miss historic sites and charming neighborhoods to restaurants where the locals actually eat. Whether it’s your first time or your tenth, this list has a little ...
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Things to do
Places to Eat
Things to do
This red-brick path winds through Boston’s most historic spots—Paul Revere’s House, Boston Common, the Old North Church. It’s like walking through a history book, but with coffee shops along the way.
Freedom Trail
If you want to slow things down, this is the place. Beautiful flowers, swan boats in the summer, and plenty of spots to sit and people-watch. It's peaceful and postcard-perfect.
Public Garden
Even if you're not a baseball fan, the energy here is contagious. Grab a Fenway Frank, tour the park, or better yet—go to a game and sing “Sweet Caroline” with the crowd.
Fenway Park
Shop, snack, and stroll. This charming street is full of boutiques, cafés, and historic brownstones. I could easily spend an afternoon here browsing and grabbing iced coffee.
Newbury Street
Yes, it's a bit touristy, but also super interactive and fun. You get to throw “tea” into the harbor and learn what really sparked the revolution. Great for kids and adults.
Boston Tea Party Ships & Museum
This museum feels more like visiting a quirky, art-loving aunt’s mansion than a traditional museum. Gorgeous courtyard and a wild story behind an unsolved art heist? Yes, please.
Isabella Stewart Gardner Museum
Cobblestone streets, the smell of garlic in the air, and some of the best Italian food you'll ever eat. Perfect for a romantic stroll or an indulgent dinner.
Guide to Boston's Little Italy
A great way to see the city from a different angle. I love this walk for the views, sea breeze, and occasional street performers. Bonus: it's free!
Boston Harborwalk
Places to Eat
Yes, there’s a wait. No, you can’t skip it. But the lobster roll here is the stuff of dreams—overflowing, warm buttered, and totally worth the hype.
Neptune Oyster
America’s oldest restaurant! Come for the history, stay for the oysters and seafood stew. Sit upstairs if you can—it’s a cozy, colonial vibe.
Union Oyster House, Boston, MA
There are a few locations, but every one of them feels Instagram-worthy. Their shakshuka and pastries are to die for. Great for brunch or a mid-day coffee break.
Tatte Bakery
No reservations, cash only, and the line is usually down the block. But oh wow—the pasta here is unbelievable. The lobster ravioli still lives rent-free in my mind.
Giacomo's Boston North End
f you’re craving something sweet, this is your spot. Get the sticky bun. Trust me on this. The sandwiches and coffee are also amazing if you're looking for a casual lunch.
Flour Bakery + Cafe
A no-frills seafood shack with some of the freshest catches around. Lobster rolls, clam chowder, fried scallops—it’s a solid stop after exploring the harbor area.
Yankee Lobster
Touristy? Maybe. But the view is fantastic and the chowder is award-winning for a reason. It’s a great place to relax by the water with a glass of wine and a plate of oysters.