48 Hours in Boston

I get asked all the time about my favorite Boston spots- restaurants, bars, attractions, neighborhoods, etc. Boston is such a unique city because while it is a major, Metropolitan city, it really has a neighborhood-y feel. Maybe this will help break ti down: “Greater Boston” (read: suburbs) is home to 4.5 million, while the actual city of Boston, where I live & play is only around 650,000.

This is what I love most about Boston! It’s truly the perfect combination of big city meets small town feel- I’ve never gotten that overwhelming feeling that I get in New York, or that too-small feel I get in Charleston, i.e. (although a FAB city!)


Without so much to see and do, here’s my suggestion for a fun 48 hours in Boston. Assuming it’s summer, of course 😉


You’ve just arrived & unloaded your bags. Perhaps you’re staying in the Back Bay rooftop pool-clad hotel, The Colonnade. Or the Beacon Hill jail-turned-hotel, The Liberty (a Starwood property for all you cardholders). Or maybe you are feeling the urge to splurge on Copley Square’s The Fairmont (if you stay here, I highly recommend a happy hour drink at the attached Oak Room- such a great people watching spot!)

PicMonkey Collage


First stop? Seaport! You’ll want to snag a spot on a roof-deck for happy hour and watch the sun go down! Legal Harborside, Sam at Louis, and The Envoy Hotel are all solid options. From here,  you can grab dinner as well! The options around Atlantic Ave are endless, but a few of my favorites are Row 34 (seafood), Del Frisco’s (steakhouse), Empire (sushi) & Trade (great cocktails & apps to share!)



If you’ve got a little steam left in you, opt for a little dancing & drinking to some live music! While finding live music in Boston isn’t as easy as I’d always like, The Fenway bars, House of Blues & Wally’s never disappoint.


Ahh, Saturday. A day of relaxing. Well, no sleeping in here, because we’ve got places to see! As touristy as it is, I always recommend a Duck Tour to my visitors (I even join them!) It’s a fun, easy, inexpensive way to see the city. You really get a feel for the history of Boston and the different neighborhoods.

PicMonkey Collage

{Back Bay/Beacon Hill/South End}

Wherever you are, it’s a good idea to stay fueled- try any of these spots & you’ve hit the jackpot:

Sam LaGrassa’s for their famous deli sandwiches

James Hook‘s famous lobster rolls (another incredible option is Neptune Oyster, if you can beat the wait!)

Island Creek Oyster for the amazing raw bar

Want pizza? Try Regina’s Pizzeria (try the Mediterranean), or Area Four, or Picco, or Salty Pig, or Coppa…the list goes on!

PicMonkey Collage

{Reginas/Area 4/Picco/Salty Pig/Coppa}

Any given Saturday, there are many events going on in Boston. I recommend checking out the calendar to see what’s happening: you could attend a Red Sox game at Fenway Park (an amazing experience!), or head on over to a tour of Harpoon Brewery (be sure to get a beer flight & a pretzel!), or walk around the shops of Newbury St, tour the Boston Public Library, and take a stroll through the Boston Commons & Boston Public Garden. Don’t forget about Quincy Market & Faneuil Hall– always an entertaining site.




**Did I mention that you will be walking all over town? Bring comfy shoes- we are a true walking city!**

For the evening, I recommend the North End. It’s the authentic Italian area of town & it’s so charming. The tiny streets are lined with amazing restaurants, bakeries, shops & bars. You really can’t go wrong here, but everyone seems to have their favorite. A few of mine include Strega, Bricco, Giacomo’s & Antico Forno.



Finally, you MUST try a cannoli! The never ending battle is Mike’s vs. Modern. Try one of each & you decide!


It’s your last day here, but don’t be sad because it’s Sunday Funday! Let’s get some exercise in this morning, shall we? You could do a spin class at Equinox, a yoga class at Back Bay Yoga, drop in for Pure Barre, or take a 3 mile jog around the Charles River…obviously, this is the best option.


From here, it’s time to brunch! Some amazing local spots are The Beehive’s jazz brunch, Lincoln Tavern sports bar/restaurant in Southie, Myers + Chang for dumplings, or Mike’s City Diner for good ole’ bacon & eggs.

After brunch, take a stroll down to the SoWa market- an outdoor marketplace full of food trucks, local farm stands, vintage clothes/goods, and a plethora of art galleries. It’s always a fun event & worth checking out! Plus, you’re only about 15 minutes away from the airport 😦



{all of the fresh veggies @ SoWa!}

As you can see, Boston is a city full of food, history, water & walking! I cannot recommend coming to visit enough. I promise, you won’t be disappointed.


4 thoughts on “48 Hours in Boston

  1. Pingback: Link Love | A Healthy Slice of Life

  2. Pingback: 2015 Roundup | SouthEndStyle

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