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top five guide: boston, massachusetts

Updated: Sep 7, 2023

Boston Massachusetts old and new buildings

In the summer of 2021, my husband surprised me with a long weekend trip to one of America's greatest cities: Boston (surprise trips are my love language, by the way). With charming walkable and bikeable streets, historic sights around every corner, and an excellent food scene, Boston is a treat for all the senses. An ideal weekend destination, the compact and walkable nature of the city makes it too easy to explore a great deal in a short amount of time. And that's exactly what we did.

By the way: unlike popular stereotypes, we found the people in Boston to be incredibly friendly, which was honestly kind of disappointing.

Here are my top five tips for a trip to Boston:

Neptune Oysters Boston Massachusetts lobster rolls rose

1: lobster rolls

American cuisine is delightfully regional, and any visitor should make an effort to try whatever fare said region has to offer. When it comes to the Northeast, lobster rolls should be at the top of your list. We had two incredible rolls in Boston. The first was at Neptune Oyster (pictured), a deservedly famous spot in North End that almost always has a wait. The second was at B&G Oysters, a charming gem we stumbled upon while exploring a quiet, shady street in South End. Their sunken courtyard was particularly ideal for enjoying the sunny summer weather. You can't go wrong with either!

Fenway Park baseball game hot dog Boston

2: a day at fenway

Whether you're a true baseball fanatic or just interested in the beer and hot dogs, you cannot miss a game at Fenway Park, America's oldest and arguably most famous MLB stadium. If you are lucky enough to visit during baseball season, it is a marvel to behold the heritage of the game and the passion of Red Sox fans. We were lucky to witness a Red Sox v. Yankees matchup, which was a bucket list experience (and the Sox won!). Be sure to show up at least an hour or two early to participate in the tailgate parties around the stadium, and don't miss popping into The Bleacher Bar.

Modern Pastry cannoli Boston Massachusetts North End

3: north end

The North End (aka Little Italy) is one of Boston's most historic neighborhoods, packed with adorable family-owned Italian restaurants and buzzing at night. It’s a must visit for dinner, but be sure you make room for dessert! A Boston rite of passage is having cannoli from one (or both) of the city's longtime shops: Mike's Pastry and Modern Pastry. We tried both and can attest they are worth the (often long) wait. Only have time to pick one? Mike’s has more “exotic” flavor options like peanut butter or hazelnut (all $5). Modern sticks to traditional options, and also has a full bar (espresso martini? hell yes.).

Cambridge Massachusetts Harvard University Boston

4: bike to cambridge

Visiting Boston in July rewarded us with ideal sunny weather that begged for outdoor activities. If you are lucky enough to have pleasant weather during your stay, you should rent a city bike (only $10 for 24 hours) and take a mostly flat 30-minute cruise along the Charles River path to Cambridge, a charming little town that is home to two of America's most prestigious universities: Harvard and MIT. Be sure to check out Harvard Square and the many restaurants on Massachusetts Ave. We enjoyed drinks at Alden Harlow while we pretended to be Harvard students.

Tatte Bakery Boston Massachusetts Back Bay

5: tatte bakery

Tatte Bakery is a Boston favorite, with a few locations across town (though my favorites were in the Back Bay and Beacon Hill neighborhoods). An adorable and lively spot for breakfast, pastries, or coffee, it's an ideal place to start your day before exploring the city. Everything we got there was delicious!

Have a great trip! Feel free to leave a comment with your own favorites. You can also find these recommendations (and more!) in map format by following me on the Out of Office app.


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