Boston in 48 Hours

This weekend was a joyful whirlwind.

Our dear friends Elliot and Lena came in town to visit and we had a grand time showing off our favorite parts of Beantown. It was 48 hours of serious touring, and it was bittersweet to realize that this would be the last time that we show any of our friends around Boston while we still live here. With our move coming up at the end of the month, we will be bouncing around a few cities (and countries!) this summer and then finally landing in NYC in August. That realization made this weekend all the sweeter.

Spending this weekend with our friends made me realize that many people are weekend travelers. They want to see the best of a city in about 2 days. Since I've lived in Boston for about 2 years now, I thought I would share my favorite itinerary for Boston's sights. If you have an inkling to visit Boston for a weekend but aren't sure quite what to do or where to go, look no further. I've got your back. Here's a doable (haha, sort of) itinerary to give you the highest points of Boston:

Friday Eve.


// Arrive Boston. It's dinnertime. Best spots in Harvard Square are Russell House (American-style pub), Park (delicious Northeastern vibe), Bertucci's (slammin' Italian pizza, I don't care that it's a chain), Wagamama (Japanese fusion with delicious fresh juices). Any of these will do. Note: If you're rolling in the benjamins, stay at the Charles Hotel. If you're not quite rollin', stay at The Inn at Harvard, or if you're lucky enough, crash on your friends' couch.


// Whoopie Pies at Clover Food Lab. These are made fresh, only on Fridays, and GOOOOD. Don't miss this simple and satisfying dessert. 


// Drinks at John Harvards. Order the sampler, it's always changing and always good. Look around the bar tables and get a feel for the college students in this joint. Pretend you're in a finals club (Harvard's version of a frat) and attempt to sneak into one of their parties. Obviously.


// Drinks and Live Music at the Plough and Stars, conveniently located within a super short walking distance to our apartment. Order the Dark and Stormy. You won't be disappointed.



// Coffee, my Mango Coconut Baked Oatmeal and H20. You will need it for the following:


// Freedom Trail Run. This 5k-length running tour of the 17 most historical spots in Boston gives you all the history you want, at a quickened pace (it would take hours to walk all the noteworthy touring spots) and this all happens before lunch. It might be hard to pull yourself out of bed after staying out until 2am the night before but it is totally worth it. You will feel so efficient, fit and like you learned a ton. But not too much.

Note: I've done this run about 7-8 times by now and it is the best tour by far. Tell Eddie-O that the Hales sent you, he is such a doll.


// Harpoon Brewery Tour. After running for 2 hours straight, give yourself a bit of a break and cab it over to this brewery on the Harbor. We waited in line for a few minutes, devoured some of Harpoon's famous German-style hot pretzels and seasonal watermelon ale, and took a delightful tour of the brewery. So. Worth it.


// Wipe the pretzel crumbs off your face. You will need a shower by now. So head back to your hotel/crash pad and take one. Bring a lightweight coat for the second half of your day.


// Tour Harvard Business School. You don't have to do this, but since it's my husband's new Alma Mater, our friends wanted to see what it was all about. You could sub in this time and take a tour of Fenway Park or walk Newbury Street. But I'm not gonna lie, the school is impressively pretty. And if you're there in the spring time, you will probably get to see the hundreds of bunny rabbits frolicking all over the campus. I have a strong theory that the school places them there purposefully, because they really add to the precious vibe of the campus. Of course Harvard would have quaint bunny rabbits blanketing their green grasses.


// Early dinner at Giacamo's in the South End. Delicious authentic Italian for affordable prices. Get the calamari. And the house pasta sauce is the best. You can make a reservation here (unlike a lot of spots in Boston), so DO IT.


// Post dinner walk in the South End towards Back Bay. We walked towards Copley Plaza and saw the Boston Marathon Bombing Memorial. Couldn't stay too long because it was still really intense and a bit too fresh on all our minds.


// Subway to the North End. This is the legit Italian district in Boston, and it is a thriving mini-metropolis of bakeries, restaurants, bars and street musicians. It's a must-see, especially since Paul Revere's House and the Old North Church are located here.


// Cannolis at Mike's Pastry. You will be ridiculed if you come to Boston and don't eat here. Bring cash. And bring your brute face; you've got to find a table in this cramped place and you won't get one by being syrupy sweet.


// Stanza dei Sigari is a cigar parlor next to Mike's. Only if you're into that kind of thing.


// Sleeeeeeeeep.


10am // Brunch at Grafton Street. So delicious. Order the seasonal cocktail, it's out of this world. You could also try out Cafe Luna or Henrietta's Table, but make sure to make a reservation a few days in advanced.


// May Day Street Fair in Harvard Square completely distracted us, but it was a lot of fun. Vendors galore.


// Subway to Park Street. Walk around the Boston Common (America's oldest established park) and the Boston Public Gardens (my personal favorite outdoor spot in Boston) because it's totally gorgeous. Feel free to stop by the Cheers bar along the side of the Garden.


// Walk down Charles Street in Beacon Hill. This is the ritzier area of the city, lots of lovely brownstones and boutiques. Imagine that you're one of the fancy people who live here with a little dog. Walk towards the water and find your way on to the Esplanade, a peninsula that juts out into the Charles River.


// Enjoy your last sweet treat in Boston at Berryline in Harvard Square. This is a local frozen yogurt place that has new flavors every week, like fruity pebbles and basil-blueberry. Out of this world. I probably live a bit too close to this place, in all honesty.

Wrap it Up.

I imagine you will be jumping on a flight back to your hometown on Sunday evening. Hopefully this weekend is chock-full of all the good stuff you would want to see in Boston. I think it's a comprehensive, but doable, itinerary. Boston is a resilient, proud and classy town and there is obviously so much more to do than can be accomplished in 48 hours. A few items that would be worthwhile add-ons (in my entirely biased opinion) are Berklee College of Music, the Boston Public Library, the Minuteman Biking Trail and the Haymarket. Anything historical that I haven't specifically mentioned is most likely covered in the Freedom Trail Running Tour.

Have you ever been to Boston? Anything you would add to this list?