Want to Live in Boston? What You Should Know

I recently wrote a blogpost on how to visit Boston like a pro. I hope it was fun for you. It was definitely fun for me, but I had to restrain myself from launching into things that I recommend to people about what it’s like to live in Boston. Obviously, living in Boston is different from traveling to Boston. And therefore, I have very different thoughts.

It’s actually very interesting how often I talk to people about what it’s like to live in Boston. Sometimes it’s because I’m visiting home and someone think it’s so cool that I live somewhere as iconic and fun as Boston. Other times it’s because a friend of mine from college has been accepted to an area school, and they want my take on it. Other times, it’s because I’m traveling abroad, and someone that I meet wants to know all about Boston, a city they’ve either been to many times or never at all.

So, without further ado, here is what I have learned about living in Boston – the good, the bad, and ugly.

Boston vs Cambridge

First of all, you should know there’s a huge difference between Boston and Cambridge. I live in the latter. That doesn’t mean I prefer it though. Cambridge is where Harvard and MIT are located. I live smack dab in the middle of the two. It’s the second-youngest city in the country. Something like 66% of the population is between 18 and 34. And it feels like that. Yes, there is an astounding amount of innovation and a ton of intellectual celebrity. But there’s also a lot of douchebag undergrads that you see in any college town, because at its lowest common denominator, that’s what Cambridge is—the ultimate college town.

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“Boston” is pretty much the rest of the entire city. There are still lots of cities within it though, like Cambridge. It’s not like Chicago, where everyone in the entire city has an address in Chicago proper, but you have a distinct neighborhood like Lincoln Park. The cities of Jamaica Plain, Brookline, Chelsea, Dorchester, Charleston, and more are all distinct cities. Actual Boston is just the downtown core of the city.

Hardly anyone has an address in actual Boston. Those who do are usually either very wealthy and live somewhere like the financial district, or they have deep roots in Boston and live somewhere like the North End (the traditionally Italian district) or Southie (the traditionally Irish neighborhood). Since moving here in 2012, I have had addresses in Brighton, Allston, and now Cambridge. But all of the above run together seamlessly and I always tell people I live in Boston.

One time I told someone I lived in Cambridge, not Boston, and they took that to mean that Cambridge was a suburb an hour out of town. It’s not. My stop on the subway is just three stops from downtown (yeah, compare that to my friends who live in Brooklyn or Lincoln Park and have to take the train something like 45 minutes to get to work). Cambridge is one of many cities within the Boston metro area. BUT Cambridge is unique in that it’s pretty much self-governing, whereas Boston proper also governs some cities, like Brighton and Allston. For example, when I lived in Brighton, my address and zip code were unique to Brighton. BUT I got called into jury duty in Boston, because Boston is Brighton’s daddy. That would never happen in Cambridge. We have our own jury duty. Brookline, an upper middle class enclave known for its sizable Jewish population, is also a baby of Boston.

A Unique Experience

Now, I explain all this for a reason. That’s because Cambridge is SUCH a unique part of Boston. Living there is an experience all its own. Cambridge itself has heavily influenced my experience living here. I hardly ever interact with any proud Irish Americans from Southie whose family goes back generations, for example. Conversely, perhaps my least favorite thing about Cambridge is the fact that hardly anyone who lives in Cambridge is actually from Cambridge. If you meet someone in a bar, at Starbucks, or on Tinder who says they live in Cambridge, in all likelihood, they are a post-doc or student at Harvard or MIT. They are only going to live in the area for a year or two, before up and moving somewhere else like Stanford or Yale.

In other words, you know that really proud Bostonian with a thick accent chugging beer at Pats game in….well…any movie or TV show about Boston? I never talk to that guy. I’m much more likely to interact with an awkward gentleman from London with severe autism and an IQ of 500 who doesn’t give a fuck about the Celtics or Whitey Bulger. Now, I’m not opposed to a city full of wanderers. I myself am a wanderer. And I fucking hate sports. AND I’m gonna talk some shit about Boston, because I believe that after living here for three years, I have earned the right.

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Fenway Pak. Like I care.

BUT. I also know my place. And I also know that, no matter what, I will never be as arrogant about my opinions as some of my transient Cantabrigian (the word for someone who lives in Cambridge) neighbors. Their audacity really chaps my ass at times. At times, it truly seems like the average Cambridge resident has no respect for the city that is hosting them for their stay here. In that sense, Harvard truly is an ivory tower. For example, one time I was at a bar in Harvard Square. I was waiting for a friend or something, and eavesdropping on the conversation of four people behind me. They were all Harvard grad students. One of them asked another how he liked living in Boston. His response was, “Meh. To be honest, I really like living in Cambridge, but that’s because I don’t like most people from Boston, and I can avoid them.”

Is that not the shittiest thing you’ve ever heard? I found myself wishing that we WERE in Boston, so that some local would fucking kick his ass. But I also realized at that moment that THAT exact type of arrogance was the reason I didn’t love living in Cambridge. I mean, I do like living in Cambridge. I love living just two blocks away from great sushi, Indian food, and affordable wine. But I do not love it. And I believe it’s because that attitude is so pervasive.

Interestingly, I was having a conversation about my future with a good friend a few evenings ago, and this topic came up. Unlike those douchebags I was talking about before, she is a die-hard Cambridge fan. She has lived here for something like 20 years and loves it. She can say whatever she wants about it. I also love her to death. But, when I told her that I didn’t want to live in Boston my whole life, she responded with, “Well, I don’t want to live in Boston either. Cambridge is a different story!” She, like a friend of mine who recently moved back to Boston after a little adventure in Chicago, loves being surrounded by some of the smartest people in the world. I get that. It’s exciting to be able to learn something new everyday, and interact with perhaps the next Mark Zuckerberg when you’re in line at the grocery store.

But, as you can probably guess, gun to my head, I would likely rather live in Boston than Cambridge. Yes, Cambridge is as blue as it gets, and I love that. There’s great food. It’s close to work. But, I will not work at Harvard forever. I will also not live in Cambridge forever. Because I want to eventually meet normal people. I want to meet people who actually have a connection to their hometown. I want to meet people who aren’t post-doctoral fellows. I want to log onto Grindr and NOT READ WHAT YOUR THESIS IS ABOUT! Yes, guys in Cambridge actually put that information in their Grindr profiles. That, to them, is the most interesting facet about themselves that they can come up with for potential suitors.

That said, I understand why some people may be put off by the rest of the Boston area. I have heard things about homophobia in Southie. Some neighborhoods/cities, like Brighton, for example, where I used to live, aren’t exactly hoppin’. And Boston proper (aka the downtown area) is pretty sleepy. Bars close are 2. It’s hard to find good pizza. And Mexican food.

But there’s an energy and a loyalty to the population that identify as true Bostonians that will always fascinate me. I also think that Boston accents are somewhat adorable/sexy depending on the person. True Bostonians don’t give a fuck about your Ivy League pedigree. They’re not impressed with a restaurant that charges $20 for a sandwich. They swear by Dunkin Donuts, and you can take your Starbucks latte and shove it. Call me crazy, but I can get down with that crew.

Location, Location, Location

Now that I’ve bitched a little about Boston, I want to talk about my favorite thing. I don’t think that I will ever be able to visit all of the places that Boston provides easy access to. I’m serious. As I mentioned here, I made a list a year ago with all the places I wanted to go, and I quickly realized that literally an ENTIRE YEAR is not enough time to see everything. Think about it. Whether it’s a historical site, a beautiful beach, or an enclave of artists, there is SO MUCH to do and see, it’s a wanderer’s wet dream.

First, let’s start with things inside the city limits. Did you know Walden Pond is basically in Boston? It is, and I still haven’t been. There are also all the spots along the Freedom Trail that I mentioned in my last post, especially the Bunker Hill Monument and the U.S.S. Constitution. Oh, and don’t forget about George Washington’s headquarters during the Revolutionary War, just north of Harvard Square. These are but a sampling of the many famous and fascinating places you can get to in under a half hour on the T or under twenty minutes in a car.

Next, let’s expand the radius. How about a couple hours outside of town? Ok, well, you can go Martha’s Vineyard, or Provincetown. Both of those Cape Cod legends deserve a full weekend of exploration. Or you could easily spend just as long thrift-shopping and exploring in Providence, which is one of my favorite cities. Have you heard of Firewater, where the entire city gathers basically every month for a huge citywide bonfire along the river that bisects town? It’s a truly unforgettable experience. You could also spend an entire summer relaxing and rejuvenating in the Berkshires, just west of the city. Or go north to Maine for really any kind of activity you could envision. Beaches (Wells), artist colonies (Ogunquit), headshops and hippies (Portland), historic resorts (Kennebunkport), and stunning national parks (Acadia) all await you. Whether you want to go back to nature or forward to a progressive vision of the future filled with recreational marijuana and more breweries than you can count, Maine has it all. OH. And don’t forget the other things back in MA. Lizzie Borden’s house. Or Salem! You guys. The list just keeps going.

Okay, let’s expand the radius even more. Let’s say four hours. In four hours, you can get to New York City (which I have done at least half a dozen times since moving to Boston), or Canada. Or, like we did last Thanksgiving, find yourself a beautiful cabin in the snowcapped but cozy mountains of Vermont. Ski the day away. Alternatively, if you’d rather spend four hours in a plane, you can fly to Iceland or the Azores for cheaper than you can fly to California. And don’t even get me started on flying somewhere in under four hours. Washington, D.C., or Philadelphia, anyone?

Sometimes I think about moving to Chicago, so I can be closer to my parents or whatever. But then I think “wait, where would I go?” and remember how good I have it in Boston.

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I just typed Boston into Google Flights on some random day in March. Look at these cheap ass flights! Notice Miami and Madrid.

Get Ready for It

Ok, so negative again. Living in Boston is ridiculously expensive. I cannot underestimate this enough. It’s so expensive that I would never, ever, be able to even entertain the idea of owning property there. Unless I married a sugar daddy. It’s almost impossible to find a house for under a million dollars in any area within a half hour drive of anything you want to get to. If you want to own your home in Boston, and you are not making six figures, you will have to resign yourself to living somewhere boring as hell. I am not going to live in Framingham or Billerica.

Now, if you’re like me and want to rent, there’s not much good news for you either. If you have your heart set on living in a hip, central neighborhood, you have to be prepared to pay at LEAST $1000 a month. Plus a realtor’s fee. And you will not get much for your money. Even in the shittiest, most far-out neighborhoods, you will find people paying $800 a month to live with three or four roommates.

Oh, and let’s say something about that. In Boston, your neighborhood either rocks or sucks. Most suck. This, in my opinion, is the biggest difference between living in Boston and someplace like Chicago or New York. If you want to live cheaply in New York, you can do so, and still be in a cool neighborhood with a lively and eclectic community around you. You will have a long commute, but you will find things to do in your area. And you can probably even find a cool, pre-war building with nice molding and what not. This is NOT the case in Boston. There are COUNTLESS neighborhoods that offer no charm, no interesting architecture, no nightlife, no perks at all. You may as well live in Des Moines. But without the cheap prices.

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Literally every block in every Boston neighborhood that’s not downtown. Seriously.

For the average Joe who makes ~$50k and has student debt to pay off, this is frustrating, to say the least. And it of course doesn’t stop with rent. Going out to eat costs an arm and a leg. If you’re moving to Boston to enjoy the awesome seafood, be prepared to pay a LOT for that luxury. Like $28 for a (cheap) plate. Utilities will break your bank in the winter, since most places run on gas. Health insurance, of course, is insane. The bottom line is Boston is expensive, pricey, costly. However you want to say it, there’s no getting around it. If I wasn’t living with my boyfriend, I don’t know where I’d be living, and I’d likely broke and/or pissed off all the time.


Workplace Culture

Boston has a 35-hour workweek. I like that. A lot. No one has to be at work at 8. If you do, you’re living in Boston wrong. Moving back to the Midwest would mean working at least 5 more hours a week and probably making less. Ugh. There are also a lot of really fun start-ups and tech companies, if that’s your thing. Facebook, Google, Microsoft, you name it, all have offices just down the street from my apartment. And a lot of the legit start-ups have really cool time-off policies, like “Take as much as you want, just do your job.” Which seriously makes me wonder why I work at Harvard sometimes.

That said, Boston is largely very traditional. It’s not Silicon Valley. It’s steeped in tradition, which mirrors its age and storied institutions. You don’t often meet people who work for themselves. There are a LOT of people who are “lifers” at their jobs, no matter their skillset. I understand that, don’t get me wrong. Job security is great. It’s a huge luxury. But I think that it’s definitely something that is NOT found everywhere. People work hard, they’re driven, but they don’t take risks. They like to work hard, put in their time, etc. This is nice and down to earth at times. It’s frustrating at others when the 9-5 world gets you down. Like when you’re a travel blogger who wishes he could meet other people who get sick of submitting hours week after week to the man.

Meeting of the Minds

Boston is also really interesting in other ways. You really are surrounded by some of the smartest people in the world, and that can be cool sometimes. I’ve described Boston as the Hollywood of smart people. You could be having coffee somewhere in Cambridge and have no idea that the guy next to you was President Obama’s former chief of such and such policy, while the girl you pass on the way out will be the next Mark Zuckerberg in a couple of years. I’ve met more interesting people than I could count on my hands three or four times while living there.

The Reality of those Minds

The flipside to this is the fact that getting a job in Boston is as impossible as it is to find an affordable apartment. If you move to Boston first and look for a job later, it may be many, many months before you find something that works for you. There are so many smart people competing for any and every job. And every May, thousands and thousands of graduates from Harvard and MIT with bloated resumes flood the already oversaturated market. Also, temp agencies have a monopoly over entry-level stuff. This means that if you just want a receptionist job or what not, you will have to deal with temp agencies – you’ll have to go in and meet people and hope that they can find you something, and hope that they like you more than other people vying for the same jobs, so that they send on interviews. It gets really old.

I think the reason for this is because MA has always had universal healthcare, and therefore employers must provide coverage for all employees. If you’re a temp, you’re not technically an employee, and you can then work for up to 90 days without being offered benefits. So, guess how long temp assignments are? The worst part is that, too often, companies will just swap in a new temp every 90 days. And they’re not exactly honest with their temps about what to expect. I have lots of friends who cycled through two or three different 90-day temp assignments before anyone offered them a real job. Do you think they would have stuck out the full 90 days if the company had said “we’re probably not gonna hire you full-time after the assignment ends…”

Never Forget

I know I already said this. But I think it’s important to emphasize it. It’s seriously hard to find good pizza in Boston. This drives me crazy. Also, there is ZERO Mexican food. And before you say it, Chipotle doesn’t count! Even good falafel/kebab is a crapshoot. So, in essence, the Boston food scene is nothing to rave about. Sure, there’s good (but pricy) seafood. There’s great (and even more expensive) Italian food. There’s more Indian food than you could ever eat in your life (and this is still, I would say, at least 25% more expensive than you would find in any other city). But overall, food in Boston is lacking.

Also, there’s the barscene. I don’t love it. Most are full of college douchebags looking to daterape you. And there aren’t enough gay bars. Oh, and our subway stops running at 12:30 AM. Whenever I go to NYC, I am immensely jealous of, well, everything that their nightlight scene has to offer. NYC boys, I hope you appreciate the fact that every bar is full of character, they close at 4:00, and their subway runs all night. Oh and don’t even get me started on cover charges.

Getting Around

Speaking of which, public transit in Boston is terribly inefficient and problematic. There is only one line I would recommend anyone to ever live on (the red line). Granted, it’s very nice to even have a subway. And Bostonians are encouraged to use it. And it’s very affordable compared to Chicago or NYC. But most people can’t afford to live on it anyway (I hope you don’t mind a 15-minute walk to the T from your place).

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Do yourself a favor and DON’T live on the Green line. You can thank me later.

Tiny Tim

It’s also worth pointing out that Boston is very, very tiny. If you don’t have to walk 15 minutes to get to the subway, it doesn’t take long to get most places. My commute is literally 13 minutes from door to door. Most people aren’t this lucky. But that would never happen in Chicago or NYC or LA or San Fran or Miami or insert-any-other-city-in-the-US. For the vast majority of people, there’s no reason to have more than a 30-minute commute if you live and work anywhere in the city. And don’t plan to drive.


There’s no reason to. Unless you want to be an Uber/Lyft driver. Otherwise, you will be miserable. But totally unnecessarily. If you really love driving and your car is your baby, don’t move to Boston. You will always be late trying to find a parking spot, and you will always be broke. No one wants to hear you complain about how you’re always paying to maintain your relationship with your car. Even real estate agents just use public transit or Uber to show properties! Which is crazy, considering they can get a sticker that allows them to park anywhere, anytime.

Now, if you’re still gonna move to Boston after reading this, hit me up! Let’s hang out.


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