Go Big in Beantown: Planning a Trip to Boston

First time visiting Boston? Here are some tips and places you’ll need to make sure happen, no matter how long or short the trip:

I was in Boston for a week just after Labor Day, and it was an unusually warm week for them. We were lucky with no rain, so we walked as much as we could. Being there for only a week makes me no expert by any means, but I do have some tips for those first-timers like I was just a few short months ago.

  1. Walk as much as you can, wear comfy shoes, & go light for your bag/purse
    Boston is one of the best walking cities I’ve visited. Put your destination on Google Maps and switch it over to the walking directions. The majority of the city is on a grid system, making for easy walks that are packed with great people-watching and sightseeing. Make sure you pack those comfy shoes though, and lighten up on what you carry. We made the mistake of wearing the wrong shoes on the first day. We had some killer blisters by the end of the day, and our shoulders hurt from the amount of stuff we carried in our purses. Please, learn from our mistakes!Here’s what I had in my purse on the last day, after I had become a “pro” (I use that term oh-so loosely):
  • Phone
  • Sunglasses
  • Small coin purse big enough for driver’s license, a bit of cash, my hotel card, and my credit card
  • Chapstick
  • Portable battery charger for my phone (you’ll need this!)
  • Ponytail Band
  • Band-Aid (in case of blisters)
  • The Freedom Trail map
  • Let me just re-iterate on the comfy shoes part one more time…I took pictures of my feet at the end of the week just to remind myself for future trips…it’s that bad… I’ll spare you by keeping my feet off the internet but, just know, you have no idea how many different types and places you can get a blister until you’ve worn the wrong shoes in such a walkable city.
  1. Splurge on the Freedom Trail tour, and do it early in your trip.
    I know, I know – it’s so lame to be the “tourist”. But forget about fitting in with the locals for a second, and make sure you take this tour. Boston is packed with such interesting historical landmarks – you just can’t pass up this tour. The tour guides are dressed as if they are a famous colonial-era figure, and tell stories and facts about Boston you can’t get anywhere else. We made a point to go on this tour our first day of Boston. This helped tremendously as we navigated throughout the city for the rest of the week, and we ended up using the Freedom Trail map as one of our main references for the rest of the trip. (Make sure you have some cash to tip your guide at the end!)60605141-BD4D-48A2-BCED-F96BF31B8376
  2. When it comes to food, you gotta go big but also, ask the locals.
    We went to Boston with a list of places to eat and/or drink, many of which were famous for one reason or another, such as Union Oyster House (open continuously since 1826), Mike’s Pastry, or Giacomo’s (consistently named Best Italian). However, if you’re only in the city for a short while, these line-out-the-door places may not work for your dinner schedule. Who cares if you’re not eating at the normal dinner hour? You’re in Bah-ston. Go in the later afternoon or for an early dinner so you can try some of these places where the line is slightly shorter.After hearing about the history of the Omni Parker House on the Freedom Trail tour, we decided to end our tour back in their bar for a drink and a taste of the original Parker House-style rolls and a piece of Boston Crème pie (Omni Parker House is where this tasty treat was created). We asked our Boston-born-and-raised waiter where he liked to eat, and he shared some places with us that were the food highlight of our trip! Places that we wouldn’t have known about, otherwise.Some of our favorites:
  • Carmelina’s: (North End: Authentic Sicilian comfort food) Make sure you call ahead and put your name on the list. This place was so good, we went twice. And we never do that on a trip. The atmosphere is cozy, with a tiny dining area and an open air patio area if the weather is nice. The staff here is friendly, with the most perfect thick accents, and helpful in suggesting good dishes. We got to sit at their counter, practically IN the kitchen, and watch them make our food. Our favorites were the Sunday Macaroni and the Carbonara. The Carbonara remains in my top-five ALL-TIME favorite dishes. I honestly think no other Carbonara can beat it. (sorry, Dad.)


  • Neptune Oyster: (North End: Amazingly fresh oysters, seafood) This is another cozy place, with only a few tables and a long bar; however, it is a bit of a wait since you cannot make reservations. We went there for an early dinner, put our name on the list, and then walked around the little shops of the North End. We told our waiter to surprise us with the best, local oysters on the menu; and he did not disappoint! We also split the Cioppino and the Lobster Roll (which was decadent: make sure to get it hot, with butter!)
  • Trident Café: This little place is in the upstairs of the Trident Bookstore, which sits along Newbury St. It was the perfect little breakfast to start off our major day of walking. If you go for breakfast, you MUST get their Mega Tots, which are gigantic tatertots stuffed with melty-gooey cheese. Don’t even think twice about it; just do it. You’ll walk it off later anyway, right? Make sure you leave a little bit of time to browse the bookstore: they’ve got a great gift and book selection.C51C21AE-DE41-4516-9BCE-469F37FCBB3D
  1. Head Over to Harvard and MIT
    Walk or rent a bike and ride it over the Charles River on the Harvard Bridge. It’s really not as far as it seems, and you get some great people watching, especially on a nice day when the school crew teams are rowing down the river and the locals are out enjoying the weather. Almost as soon as you cross the bridge, you’re on MIT’s campus, and about a mile down Massachusetts Ave. is Harvard’s campus. Think of all that brain power that resides within just a mile radius! But seriously, do it. It was a really cool experience to sit in the Harvard yard as students rushed to their next class.


  2. Other Stuff Worth Mentioning
    If you’re into shopping like my mom and I are, I highly recommend perusing Newbury St. It’s filled with quaint little storefronts filled with gifts, clothes, books, and a heck-uva lot more. Regardless, it’s a gorgeous little street to walk through, shopping or not. We loved Johnny Cupcakes, Trident Books, Georgetown Cupcake (yum!) and Newbury Comics.If you appreciate gorgeous old architecture, make sure to leave some time to walk through the Boston Public Library…ohmygosh… I could have sat in there all day, just staring, but I probably would have gotten weird looks. If you’re there, make sure to check out the courtyard!90E97900-D158-491D-AA35-8DA45B36AE50BCC6DF86-4D01-4BCF-AD3C-C5D6160EEAC6Like typical tourists, we did Cheers – it was fun, and a cold beer in a Cheers mug was well-deserved after a toasty, but oh-so-pretty walk through the Boston Public Garden.

    We ended our first night at Mike’s Pastry with some treats to take back to the room. They were so amazingly good! After we left, we heard amazing reviews about a similar place, called Modern Pastry. You must try one (or both!) of these places to satisfy that late night sweet tooth. Mmmm, I can picture those pastries in my head as I write this…

    The picture below is my idea of heaven…a big comfy bed and a box of Mike’s 🙂


Even though we were there for a week, part of that time was spent at a conference, so I must say: there will be a “Beantown: Part 2” in my near future! That being said, we didn’t get to go everywhere we wanted (Fenway Park, for instance.)

Have you been to Boston, or are you planning a trip soon? Let me know what your favorite places are!



Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s