Things To Do & Insider Tips From A Boston Local

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Advisor - Julia Asselin
Curated By

Julia Asselin

  • City Travel

  • Food & Wine

  • Off-the-Beaten-Path Travel

  • Boston

  • Massachusetts

  • Sightseeing

  • Sports

  • Downtown

  • Shopping

  • Foodie

Buildings in Boston.
Curator’s statement

Boston is one of the best Northeastern cities (I may be impartial) and the perfect city for a weekend getaway. Filled with history, ocean views and delicious food (think lobster rolls & Italian foo,) this city is clean and walkable. From Fenway to the North End, you won’t be short of things to do or places to eat!

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Where to stay in Boston, Massachusetts

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Things to do in Boston, Massachusetts

Boston skyline and trees in the winter.

Freedom Trail - This is baseline, as touristy as it gets. BUT I take everyone who visits me on it, or at least part of it. If you’re not super into the history, I get it, but it’s the BEST way to see a majority of the city. And you can add a few pub stops along the way to keep things interesting.

Harvard University/Cambridge - People that come to Boston seem to be obsessed with going to see is worth a quick look around, grab lunch at one of the restaurants in Harvard Square or head down for a walk along the Charles (great view of the city from there. )

Red Sox Game (or Red Sox Stadium Tour) - A classic Boston staple, if you can catch a game here, do it for the atmosphere even if you don’t love baseball. There’s a lot of history, drinking and good food to be had around the stadium in Fenway. And if you’re visiting off of baseball season, they still offer year round tours for $21.

Acorn Street - Beacon Hill - “The Most Photographed Street in the Country.” I wouldn’t recommend it if it wasn’t actually worth it. Plus, strolling around Beacon Hill is dreamy. The cobblestoned road does gain quite an audience, so be prepared to wait in line for a photo or have people in the background; unless you’re really dedicated and get there early in the morning.

Fan Pier Park - Seaport - This spot gives you a fantastic view of the other side of Boston, plus the water and boats coming in and out of the harbor. This spot at evening/night time is even more magical when the city lights come on. Even if you don’t get a photo, it’s worth checking out.

Newbury Street - Back Bay - Ah Newbury Street. I remember when I first moved here I wanted to live near it. Now I can’t tell you the last time I was there. Newbury street is basically shopping and eating, you'll find mainly tourists and college students around here. But you can find the classic Brownstone homes in this area, and if you go one or two blocks back to Commonwealth Ave, is a great photo op.

Day Trips

  • Salem, MA

  • Cape Cod, MA

  • Newport, RI

Place to eat & drink in Boston, Massachusetts

Craft hip coffeeshop in Boston.

Where To Eat

Lolita - Lolita is a Mexican restaurant based in the Seaport/Fort Point neighborhood of Boston. Famous for delicious margaritas and tacos, they also have incredible decor and vibe indoors. Think: Day of the Dead meets underground Speakeasy… Auring the summer they have outdoor seating on the water. And if I haven’t convinced you yet, at the end of each meal they bring out complementary cotton candy with the bill. If you want a dining ~experience~ this is the place to be.

Trattoria Il Panino - They are based in the infamous “North End” or the “Little Italy'' of Boston. Offering all the homemade pasta and wine you could dream of, this is the place to dine (skip Giaccomos, they don’t take reservations and you’ll probably wait an hour to sit in a crowded restaurant with decent food but they’ll rush you in and out) Also skip Mike’s pastry after and head to Bova’s. Shorter line and similar (or better in my opinion) pastries.

Fox & The Knife - Another Italian recommendation, but has won awards and has been featured in Conde Nast Traveler. They’re best known for homemade pasta and modern cocktails. This spot definitely needs reservations (weeks in advance,) but if you can score one, it’s a hit. Please get the focaccia, and thank me later.

Where To Drink

Lucky’s Lounge - Seaport - This is a rowdy, infamous late night spot. One of the only “dive bars” in the flashy Seaport area. My understanding is you want to be properly … inebriated before you enter. But everyone has a great story about a night at Lucky’s and apparently their food is actually decent. It is also a late night spot, open until 2am when all other bars close at 1am.

The Lincoln South Boston - This bar is a purely local bar packed with 20-somethings from 8pm Friday-7pm Sunday. All day and all night. South Boston is notoriously known for “yuppies," which are the kids in their mid-twenties who have graduated college, moved here and work in the city (myself included.) And they LOVE to party. Honestly, any bar in South Boston you’ll find the same scene all weekend long. Need I say much more?

The Black Rose - As far as Irish Pubs go, this one hits the nail on the head. There is usually some kind of live Irish music happening, plus if you get tired of it, there are about a million other bars in that area to pop into. Be warned - there will be a lot of college kids here/around here. Plus, quite a few tourists.

Advisor - Julia Asselin

Travel Advisor

Julia Asselin

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This guide is part of our ongoing series on travel to Boston.