Boston Proper: A Quick Guide to the Best Neighborhoods

Boston is an awesome city to visit (and to live). As one of the oldest cities in the US, Boston has lots to see and do. But where should you start? How should you organize your trip to maximize your Boston adventures? These questions can become overwhelming if you consider the total of Boston’s sprawling 23 neighborhoods, which doesn’t even include Cambridge!

Let’s be honest though – you’re not really interested all 23 neighborhoods just now. Not that each neighborhood doesn’t have something to offer, but I’m guessing you want the historic stuff, the food, the bars, and the charm. Below is a map outlining the 10 neighborhoods of Boston Proper that offer more for visitors. If I’m brutally honest, its really probably only 5 of these neighborhoods that you really want to explore – especially if you’re only in Boston for a few days.

North End

North Square Boston in the historic North End. The place to come for everything Italian — including cannoli

This is where lots of Italian food can be found, but be sure to make a reservation! Also some great bars and old stuff. There are many ways to enjoy the North End — grab a delicious Italian treat and chill in the North Square Boston or splurge on a pizza tour. Checkout Parla for creative drinks and ImprovAsylum for some great comedy!

Beacon Hill

Acorn Street in Beacon Hill, dubbed the one of the most instagrammable places in Boston

You know when you see pictures of cobbled streets, brownstone houses, and beautiful flowers? That’s Beacon Hill, one of the most instagrammable places in Boston. Beacon Hill has a mix of restaurants, bars, shopping, and history.

A quick note: this neighborhood is not all cobblestone streets, in fact, most streets are not cobblestone. Even without being all cobbleston streets, Beacon Hill is a beautiful area for a wander! Boston Commons are here too.

Downtown / Financial District

Historical tours are often seen in the Downtown Boston area, particularly here at the old State House

I’m including the Greenway in this area. This area includes Faneuil Hall, Quincy Market, Chinatown, Downtown Crossing (shopping, more generic than Beacon Hill), Theater District, and the Financial District (banks, businesses, and Kanes Donuts).

Also, Granary Burial Ground, though this could be considered to be Beacon Hill.

Back Bay

Boston Public Library is one of my favorite places in Boston. Books and possibly the best high tea in Boston can be found here

High-end shopping on Newbury St., the Public Gardens, brownstones, Boston Public Library, and, generally, more upscale dining.

Hit up Butermilk & Bourbon for brunch and the Boston Public Library for some of the best high tea in Boston! I highly recommend making reservations.

South End

SoWa Market, open Sunday mornings; eat, drink, shop, and enjoy the fresh air. Here you can also hit up the South End farmers market

Not to be confused with Southie, another Boston neighborhood. I recommend visiting the South End farmers market in SoWa Market. I don’t know about you, but I’m a big fan of food and food trucks — another reason to hit up SoWa.

West End

Canal St bars, just around the corner from TD Garden

Home to TD Garden, a bunch of sports bars, and Boston Public Market, which is actually in the Greenway, but borders West End and North End. I really enjoy Boston Public Market with its diversity of food options and artisan stands.

If you find yourself looking for a drink and/or a bite to eat, check out the Canal St bars, conveniently located around the corner from TD Garden and maintaining some of the old Boston charm.


Where the Red Sox play, lots of colleges (and college kids), bars, Time Out Market, and museums. Be sure to check out the Museum of Fine Arts and the Isabella Stewart Gardner Museum.


Brewery brunch? Chow down on seafood? Museum on the water? All can be found in Seaport!

The Seaport district is newly developed and plays hosts to numerous conventions and expos. If you’re interested in the idea of a brewery brunch, check out Sunday brunch at Harpoon – they host brunch one Sunday a month.  If you’re timing is right, this is a good place to enjoy some beers and pretzels.  

Looking to enjoy some seafood on the water? Check out The Barking Crab. Museum lover? Head on over to the Boston Tea Party & Ships Museum.

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  • Ciaran

    A great read! It was very informational. I go to Boston a lot and I still learned something new.

    Keep up the great work.


    • thisunsettledlife

      Thank Ciaran! Super glad you got something out the read!

  • Jeannie Vandenberg

    I love it, now I just need to visit Boston!

  • Rachel

    this makes me miss Boston so much. such a fun city! great post!

    • thisunsettledlife

      Hi Rachel! I totally get it; Boston is pretty awesome city 🙂

  • Amanda

    Such an awesome post! I used to live in Boston (Charlestown) and the suburbs (both north and south). My hubby and I visit for a long weekend every other year. 🙂

    • thisunsettledlife

      Thanks, Amanda! That’s great that you still get back to visit!

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