The Do’s and Dont’s of Boston Travel

Following up on Jess’s blogpost about what to see and do in her favorite city, New Orleans, I thought it appropriate to write about what to do in my (new) hometown, Boston! I’ve lived in Boston for going on three and a half years, and I consider myself an EXPERT on what to do if you’re traveling here, because I can’t even count on one hand the number of friends and family that have visited me here in New England. Or my boyfriend, who usually tasks me with figuring out the best sites for their short stay.

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So, if you’re traveling to Boston, you’ve probably heard about all the places you need to go. Or you’ve probably at least heard about the most famous things that everyone does. So, without further ado, here are:

  • Some things you SHOULD do, see, or experience in Boston
  • Some more things you should NOT do, see, or experience while here.
  • Finally, some places I’m ambivalent about but some people will tell you that you have to go to them anyway, and I’m not gonna have a cow about it if you do.

Yay! Now. Let’s do this.

A glimpse of Chinatown. Which is definitely worth a stroll. Though don’t expect much. It’s TINY. It shouldn’t even be called Chinatown. More like Chinablock. Photo courtesy of my good friend, Meritt Suchomel, of Parker, CO.


You Should Do/Go To/See:

  • The Freedom Trail (North End, USS Constitution and Bunker Hill): Ok so if you don’t know what the Freedom Trail is, it’s a collection of historical sights all over downtown Boston that are connected by a stripe of red sidewalk. To walk the entire freedom trail takes a whole day, and I wouldn’t recommend that unless you are super hardy and the weather is nice. Still, there are some highlights that I take everyone who visits me to.
    The first is the North End. This is my favorite area of Boston. It’s the traditionally Italian district, and the food scene today is a testament to that, though for the most part the North End today is full of yuppies. But, at times you feel like you’re walking around a European old town, and it holds quite a few top attractions on the Freedom Trail, such as Paul Revere’s house and the first church in the U.S., within close proximity of another, and is so scenic. All of these places are super old and super interesting to wander around. Oh and there’s also the Cheers bar.

    One of the like three cemeteries you can visit along the Freedom Trail filled with semi-famous dead people from revolutionary times and what not. Photo courtesy of my good friend, Meritt Suchomel of Parker, Colorado.

    Also within the North End, is Faneuil Hall, an outdoor market full of shopping and cheap souvenirs spanning a couple of blocks. It’s also the home of the Cheers bar. Do yourself a favor – don’t eat there. But buy your mom a shirt, and enjoy a stroll through one of the liveliest landmarks in all of New England.

    Then, a short walk away is the Bunker Hill monument, a tall obelisk that you can climb (for free) and get a great panoramic view of Boston. This is not an attraction for the claustrophobic or weak-kneed.

    The view of Boston from the top of the Bunker Hill Monument. Photo courtesy of my good friend Meritt Suchomel of Parker, CO.

    A bit farther of a walk away is the U.S.S. Constitution, a restored U.S. warship from the revolutionary war. This is actually a national park, so it’s also free, and it may not sound like it, but it’s very fun and interesting.

    One of the many beautiful views of the Atlantic from the North End. Photo courtesy of my good friend Meritt Suchomel, of Parker, CO.

    You might want to fit in more of the Freedom Trail, and if you have the time and energy, go for it. But you can easily spend an entire day doing just the sites I’ve listed above, and I believe they represent the best of the selection. To get there, just get off the T at North Station and follow the signs. Don’t forget to say hi to the seals at the Boston Aquarium (WHICH OTHERWISE IS SOMETHING TO AVOID – the aquarium is very disappointing. But anyone can check out the seals for free!)

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  • Revere Beach: There are many beaches within a short commute of downtown Boston, but Revere is my favorite. It’s one of my favorite ways to spend a hot Saturday afternoon. I’ll be totally honest here, the water is disgusting. Don’t swim in it. In fact, don’t swim in any water within 45 minutes of Boston. But sunbathing is great, there’s an awesome snack bar across the street (which most beaches don’t have), and there are all kinds of festivities like volleyball. My parents had a great day here, because even if the water is gross, the sand isn’t and neither is the view. It’s a great city beach, fun for all ages and not too far out. If you’re in Boston during the summer, spend one of the middle days of your trip at Revere, you won’t regret it. Take the Blue Line to Revere.
  • The Emerald Necklace: This is a bit further away from the rest of the action in Jamaica Plain. It’s a series of ponds and wooded areas that ring the southern border of the Boston area. This is not an area to visit during the winter, and maybe not even the summer, because it requires a lot of walking. But if you’re in Boston for a relaxed vacation and you’re bored of historical sites and shopping, you can’t go wrong with exploring Jamaica Plain. It’s a very nice change of pace to the rest of Boston. Not only are the views of these ponds gorgeous and refreshing after non-stop high-rises, you can also take in the views of the estates of some highly regarded Boston families. Think Larry Flint. Gorgeous homes with pillared entrances and all the windows you can imagine. Also, lots of Ethiopian food and lesbian bars. See, I told you it was a nice change of pace. Just take the Orange Line to the end and start exploring.
  • Boston Common and the Public Gardens: these green areas are located right in downtown Boston and they represent the central gathering area of the entire city. This is where all the festivals and protests go down. It’s no Central Park either—meaning you don’t need a few hours to see the whole thing. You can more or less explore it in 30 minutes, and also catch a glimpse of the State House, which overlooks Boston Common very beautifully.

Boston Public Gardens. Photo courtesy of my good friend, Meritt Suchomel of Parker, CO.

  • Kayak on the Charles River: If you don’t mind getting a little wet and have the upper arm strength, spend an afternoon doing this. I did this with the BF back in the Spring of 2015 and had a BLAST. They charge hourly, so it can be as cheap as you want it to be. It was so cool to see the city from the river, something I pass by everyday and never really think about sailing on. You’ll pass crew teams, river cruises, and lots of geese. If you’d rather take it easy, I’d recommend a river cruise, you can get very affordable tickets for an hourlong cruise that leaves from the Cambridgeside Galleria. To do either, take the Red Line to Kendall Square (but be warned: Kendall Square is one of the most boring areas of Boston. My friend who visited in January described it as a “corporate wasteland.” Just press on – the river activities are worth it!)

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  • Central Square, Cambridge: I’m a little biased about this one, because this is where I live. But I live there for a reason. Cambridge is not the hippie enclave it once was. Today’s Cambridge is overrun with Starbucks and froyo places. But if there’s any neighborhood that holds onto a taste of what Cambridge used to be, it’s my hood. Central Square is full of quirky restaurants, great nightlife, and affordable shopping. You can’t spend a day there, but you can spend a couple of hours and grab a great dinner. PLUS you can call me and then we can get coffee 😉
  • The Boston Harbor Islands: This is only an option during the summer, because the ferries close down the rest of the year. But if you are traveling during high season, the Boston Harbor Islands are a great daytrip from Boston. Now, there are something like twenty islands around the city of Boston, but you can only get to two or three. The one I recommend is (INSERT ISLAND NAME), where you can explore a dilapidated fort that was used during both the revolutionary and civil war to hold POWs. It’s a national park area, so it’s free, but you can wander on your own. It feels as thought you’re just walking all over American history, as everywhere you look are revolutionary relics. It’s great fun and there are also great views if you just want to gaze out on the ocean from somewhere not on the mainland. I went with some friends on a Saturday back in April, and though it was a bit chilly, we had a great time picnicking and exploring. But we had spacecake.
  • Allston and its assortment of international restaurants: Allston is neighborhood of Boston that gets a really bad rap, and I’m pissed about it. It’s near Boston University, so it’s full of students, and some people call it the “student ghetto.” Now, I hate students as much as the next twenty-something. Remember that episode of 30 Rock where Jack and Liz agree that “We may be bad people, but we’re not the worst. Grad students are the worst.”? I totally agree with that sentiment (current status as a grad student notwithstanding). BUT Allston is full of the BEST FOOD you will find in Boston at a decent price. I mean, if you want to spend $30 on a meal, sure, go anywhere downtown or in Cambridge and you won’t be disappointed. But if you want a steaming hot plate of Japanese barbecue or some very savory shwarma that will cost less than $8, Allston will be your favorite hood. Allston is where I discovered the Agora Café, which has the most scrumptious chocolate-filled cookies you’ll ever have. It’s also where I found O Yummy, the only Chinese food in Boston I’ve ever enjoyed.
  • Get OUT of Boston: Honestly, the best thing about Boston is its proximity to a million places in New England that are amazing in their own right. Some of them are worth much more than a daytrip, so you have to be smart about it. But if you have a day, I would recommend taking the commuter rail south to Providence, Rhode Island or renting a car and driving to Newport, Rhode Island and checking out the massive, almost grotesque mansions like the Breakers. If you like beaches, Singing Beach is north of the city and a short trip on the commuter rail as well. You could also go to Salem, which is awesome year-round for its witchy history, but especially in the fall. If you have two days, there are places in Cape Cod like Provincetown (surfing central, a gay mecca, and top destination for whale watching) or Martha’s Vineyard (celebrity sightings and all-you-can-eat oysters) that you can get to in a couple of hours either by car or boat.


Don’t worry about seeing/doing/experiencing the following:

  • New York or other far away places: Don’t be dumb. You cannot and should not try to go to New York as a side trip from Boston. NYC is FOUR HOURS away. If traffic isn’t bad. It probably will be. The farthest destination from Boston I can condone visiting is Portland, Maine, which is known for its breweries and art scene. But it’s not THAT AWESOME that if you live in like Nevada and only have four days in Boston that you should really venture that far out. If you’re in New England for a week, Portland could be a fun little diversion. But New York? Not so much. Just chill out. Keep it thematic. Be all New Englandy. DON’T be all stupid and assume that the east coast is as easily traversable as the UK. It’s not. If you lived in L.A. and a friend came for a weekend, you wouldn’t want to take them to Vegas, would you?
  • Harvard Square and Harvard University: People always want to visit Harvard and I don’t know why. I don’t mind taking them because I live right there, and I also like showing my friends where I work and spend my days. But if I lived in say, the South End or something, I would be hard-pressed to make the trek to Cambridge. This is because, just being honest with you, most people who go to or work at Harvard are assholes. They don’t want you there. I should know, I’m one of both of those groups. All you’re doing is getting in their way as they try to go about their day. There are already so many tourists there anyway that you won’t get to enjoy any serene moments of contemplation under a tree. You’ll just get to stare at all the Asian tourists there and perhaps get to offer some of them directions. Oh, and don’t sit on the grass because Harvard doesn’t do a very good job landscaping and you’ll end up with mud on your ass (a $32 billion endowment and they can’t seem to invest in decent grass). You can’t get into any buildings without an ID either. That’s right – you can’t see the world-famous library, even with a friend. Did you know that drunk people piss and puke all over the John Harvard statue?Oh, and as I eluded to earlier, though Harvard Square used to be a funky haven for hippies, it’s nothing like that anymore. If you go to Harvard Square today, your dining options will include a number of overpriced bistros frequented by yuppies, as well as Shake Shack, Chipotle, Qdoba, Au Bon Pain, Panera Bread, Starbucks (3 of them), Dunkin Donuts (3 of them too!) and a Pete’s Coffee. Take your pick! Local culture at its finest. If you really want to do something related to Harvard, check out one of the shows at the American Repertoire Theatre or a Harvard-affiliated museum. Or just watch The Social Network.
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This pic has nothing to do with Harvard Square, it’s just a fun pic of Jess and some friends when she visited me back in 2013. Fun fact: Tom, on the right, traveled with us to Iceland a couple years later.
  • Sam Adams Brewery: No one I know who has gone to Sam Adams has ever had a fun time. They all come back complaining about the location, schedule, or prices.
  • Tavern in the Square, Sunset Cantina, Regina Pizzeria or any of the other generic bar that claims to be a Boston institution but is really just a facsimile of any other college bar with decent pizza and overpriced beer. And lots of douchebags.
  • The Boston Art Museum: If you’re a buff for American art, you can ignore this recommendation. This Boston Art Museum is probably your cup of tea. But, if you’re like me, and just a casual art enthusiast who enjoys a good museum on a rainy day, the Boston art museum will disappoint. I’ve been to museums all around the world – the Met, MOMA, the Louvre, Pompidou Centre, the Uffizi, Chicago Institute of Art, the Orsay, the Smithsonian, the Pergamon, etc I love museums. I love art. I am by no means an art historian. I do not spend more than 20 seconds reading a blurb about a piece of art. But I really do love spending a day at an art museum. And I was pretty bored at Boston’s most prestigious collection. There are some famous portraits of George Washington that may hold you over, but in general, it’s a bit of a snoozefest.
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The only piece of art at the Museum that I was inspired to photograph (or even remember).
  • Expect to Be Cheap: It pains me to say this, but Boston is a ridiculously expensive city. It is not a place to travel to if you are on a shoestring budget. An average nice hotel will run you over $300 a night, perhaps even over $400 if it’s a busy weekend. There are some really great B&Bs in Cambridge like the Irving House or Harding House, but they are still much pricier than a youth hostel. Even AirBnBs can really, really thin out your wallet. So, if you have any friends that live in Rhode Island or Maine, hit them up and commute in.
  • Driving: I only recommend renting a car if you are getting out of the city. Otherwise, take advantage of Boston’s comprehensive public transit system. Driving around will only result in massive parking fees, crazy delays, and a general disdain for humanity in general.


Finally, I’m ambivalent about the following:

  • Fenway Park: Are you a sports fan? Then go. Are you not? Then don’t. I have never been, and have no plans to. People tell me every week this is a travesty. I really don’t care. I pledge no allegiance to Boston athletics and I honestly believe baseball is the most boring sport on the planet. But if you do want to go, I can get you discounted tickets on the cheap seats. I’m sure there are good hot dogs.
  • Harpoon Brewery: I don’t like beer. But people generally say that Harpoon is more enjoyable and affordable than Sam Adams. So if you like beer, there you go. I wish you the best.
  • Duck Tours: So, a duck tour, if you don’t know, is this adventure you can pay something like $40 for, to travel around a city both on land and on water in a crazy contraption led by a very loud tour guide. You get on this big contraption that is both a boat and a bus. It looks kitschy and fun and your parents would probably like it. Unless your dad is my dad, and hates spending money on anything. I’m not that bad. I spend money quite often. But I just can’t bring myself to spend that much on one of these hokey tours. But I don’t blame you if you do.


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Bahaha. My mom loves this pic. You can do this too if you visit Fanueil Hall.




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