We don’t need to give you a lot of explanation for why we think Boston is so awesome–but we will anyway. It’s gorgeous, really historically significant and perfect for young people. There’s a reason Aaron returned home from Richmond and Karen came here for college and never left. (Well, besides Aaron) Though we now live in the suburbs, we make every effort to venture into the city. The dining is among the nation’s best and the incredible amount of colleges make it a fun drinking town. If you’re in it for the long weekend, we definitely recommend flying into Boston and doing a night in our hometown. Hotels are easy to come by in the city, so selecting an option is really up to what neighborhood you’d like to be in, whether you’d like to be near public transportation, etc.  We like the Holiday Inn on Beacon Street in Brookline, the Hyatt Regency on Memorial in Cambridge (It’s right on the Boston line; Karen lived here for her first semester at Boston University!) or the Sheraton in the Back Bay. But really any hotel in the downtown, Back Bay or Beacon Hill areas will suit the bill.

If you do get a chance to spend some time in Beantown, we recommend making a few stops in some our favorite places.


Local Attractions

What Where Why
Faneuil Hall Directions The Faneuil Hall area is home to an open air marketplace that’s come to be more commercial than historical but still has a lot to offer the greenest tourist. Nearby, the site of the Old South Meeting house and the Boston Massacre will make you wonder why your teacher spent so much time talking about a tiny event. More modern additions include the stunning Holocaust memorial. A must visit for any tourist.
We Recommend: Grabbing a bite to eat and watching one of the many street performers that fill the sidewalk on any sunny day.
Freedom Trail Directions We don’t need to tell you how much awesome historical information Boston has to offer. Get it all in one go by way of the Freedom trail. A self-guided tour begins in Boston Common and ends at Bunker Hill in Charlestown. You’ll get a great walk across the city and gain a ton of cool Boston facts. It is INSANE how much happened here!
We Recommend: Upping your tour ante and going on a guided tour with an 18th century costumed guide.
Fenway Park Directions Home to the greatest team in baseball, Fenway Park is a national institution. Fenway is located in Kenmore Square, one of the major checkpoints of the Boston Marathon.
We Recommend: Catching a game if you can, going on a tour if you can’t. Take any opportunity you can to get inside.
Harvard Square Directions Harvard Square is not just the location of Harvard University. It’s also home to one of the most active and fun areas in the Boston area. You can go for a nice walk, hit up a number of bars, or grab a bite at some of the area’s best restaurants. You can easily find a way to waste a day here.
We Recommend: Grabbing a cupcake at Sweet and people watching from Upstairs on the Square.
North End Directions The North End was the initial landing spot for all new immigrants in New England. Initially dominated by the Irish, the area was later inhabited by Jewish families before becoming dominated by Italians. Today the North End is full of Italian restaurants and pastry shops. The Old North Church and Paul Revere’s home are also located in the area and are available daily for tours.
We Recommend: Walking from the North End to the harbor with a treat from Mike’s Pastries.
Boston Common Directions The Boston Common is not just a pretty park. Created by Frederick Law Olmstead, the Boston Common was part of the Emerald Necklace; a series of parks and greenways that extend beyond the city. It was used as a British camp during the Revolutionary war and was the site of witchcraft hangings. Martin Luther King, Jr. gave a speech here. Vietnam War activists camped out in protest. Cows once grazed on the land. To make a long story short, the Common is awesome.
We Recommend: Grabbing a blanket and catching a tan.


What Neighborhood Where Why
Boston Beer Works


Kenmore Square Directions Boston Beer Works is a small Boston franchise. In addition to typical pub grub, their menu features a lot of American fare. For those seeking out new booze, BBW also brews its own beer in house.
Gargoyles on the Square

New American

Davis Square Directions Don’t let the Somerville location deter you from hitting this restaurant. We stumbled on this restaurant as part of restaurant week and had an amazing meal. Cool decor rounds out the space.


South End Directions We love French cuisine and are lucky to have a slew of great restaurants to pick from. But, if you’re looking for a great menu, reasonable prices and super chic decor, Gaslight is your pick. We’ve done some real damage here, but that’s only because everything is so good. Plus it has free parking! In the South End! Score.


South End Directions Another great restaurant in the South End. Masa has a ‘New Mexican’ feel. Traditional meals with modern twists make this a unique restaurant with a terrific menu. Their sangria is without a doubt one of the best in the city and their brunch offers terrific Mexican twists on the classics at really cheap prices.


North End Directions There are a ton of Italian options in the North End, but Rabia’s is definitely our favorite. With the front windows open on a hot sunny night, it feels like you’re in a lush Mediterranean garden… And the pasta is to die for.


Davis Square Directions Boston has a few good barbecue options, but Redbones is definitely one of the best close to the city. Redbones offers Memphis-style barbecue with pork, fish and vegetarian options. The basement bar has a wide beer list.


What Neighborhood Directions Why
Drink Fort Point Directions Drink is a great bar in developing Ft. Point. Drink bartenders talk with you to create a “drink profile” and make great drinks you’ve never heard of.  No real beers here, but if you prepare for the best cocktails of your life, you won’t be disappointed.
We Recommend: The Cucumber Gin Fizz – One of Aaron’s favorite’s
Deep Ellum Allston Directions We used to hit this bar up every weekend when Karen moved into our apartment in Allston. 28 drafts, 80 bottles and a rotating list of delicious cocktails make for a great meal. The outdoor deck on a summer night make this a must-hit.
We Recommend: The Best Wurst Plate and any cocktail.
Sunset Grille
& Tap
Allston Directions Sunset Grille is known for having the biggest beer selection in Boston. 112 beers and 380 bottles can make picking a beer a big decision. A college hot spot during the school year, it is a great spot for a drink on a nice, summer night.
We Recommend: The Bourbon BBQ Steak Tips and a Beer Sampler with at least 3 you’ve never heard of.
Purple Shamrock, Ned Divine’s,
Henessey’s & Black Rose
Faneuil Hall Directions Faneuil Hall is a definite tourist spot, but it’s also the mecca for all the big Irish pubs of the area. Take your pick from any on this list and you’ll be guaranteed to have a great time.
We Recommend: Grabbing a pint of Guinness and singing along with a group of Irish buskers.
Bleacher Bar, Cask ‘n Flagon,
Game On & Lansdowne Bar
Kenmore Square Directions Can’t grab a ticket to a game? Watch the game like the locals on Lansdowne Street. Get there early and grab a seat at the Bleacher Bar, located inside of Fenway Park. Good strategic placement will get you a perfect view of the game from center field.
Temple Bar Harvard Square Directions After doing your best Good Will Hunting impersonation, head over to Temple Bar in Harvard Square. Besides being gorgeous inside, the drinks and food are great too.