Let’s be honest here, you and the girls are in need of a getaway, a chance to explore somewhere new, take a break from the stresses of home, and make some new memories together. It’s time and I have for you here the perfect girls getaway and must-do activities to check off the list, complete with culture, history, sports, drinks, good eats, and lots of opportunities for fun. Use this girl’s guide to Boston to plan your next getaway and make the most of this beautiful city!
When To Go
Summers in Boston are on a whole other level of lovely. We wait all year for our cherished three months of summer and when they arrive we celebrate in style, spending as much time outdoors as possible. You’ll have the best time exploring this very walkable city if you come in summer. That being said, the late spring and early fall are also excellent times to be in town, with the added bonus that all the college students are still around. Boston is home to over 300 colleges and universities, so when all the students are here and school is in session there’s a busy excitement around Boston. And as for winter, even though I’m a Boston girl and the city’s biggest fan, I can’t recommend that you come visit in winter. (At least not your first visit!) We get a bit grouchy in winter because after the first blizzard or two we don’t want to see any more snow, and yet the snow keeps falling. Come in summer, you’ll love it!
How To Get Here
Planes, trains, and automobiles. Boston Logan Airport is our home airport and from there you can take the blue or silver line on the T to get into town, or just hail a cab because it’s not that far. You can also get here relatively easily by Amtrak train, we’re just a 3-4 ride from NYC, and the train stops twice in Boston, at Back Bay and South Station. As for automobiles, well I might not recommend it. Once you’re here, you won’t want to be driving around. We’ve got all these confusing winding roads that are beautiful and a pleasure to navigate by foot, but will make you hate the city immediately if you’re trying to drive on them. Plus parking is expensive. And anyways, all the highlights and attractions are within walking distance here in Boston so you’ll be fine without a car!
Where To Stay
You have no shortage of options when it comes to where to stay in Boston, but I’ll highlight some of my favorites because I believe that picking the right accommodation can really elevate your entire trip!
The Envoy Hotel, Autograph Collection
This sleek modern hotel will dazzle you as soon as you walk into the lobby. It just opened last summer and is one of my favorites because it has the absolute best views of the Boston skyline! Plus you can get your night started with a classy cocktail on the rooftop bar and really enjoy the views!Book Here
This luxury boutique hotel is located in my favorite neighborhood of Boston, in Beacon Hill. It’s utterly charming and comfortable, with a killer reputation for service, in a great location. The secret’s out though because Travel + Leisure just named it the second best hotel in all of the US!Book Here
I’m a firm believer in airbnb as a way to stay that makes you feel like part of the local scene. The trick though is to find the right neighborhood! In Boston you can’t go wrong staying in Beacon Hill, Back Bay, or North End, which are the oldest and most historic neighborhoods in town. There’s a cool hipster vibe going on in South End, but don’t stay more than a few blocks from Back Bay Station or else you’ll have a lot more walking to do. And of course you’d do well to stay in Kenmore Square near Fenway Park, where all the Red Sox action is!Book Here
What To See
#1 Faneuil Hall – This marketplace used to be where ships brought their goods in to sell and now it’s a bustling collection of stores and restaurants, accompanied by an impressive lineup of street performers. It’s actually the 3rd most visited public spot in the US (after Times Square and the Vegas Strip) and is a fun epicenter of tourist action.
#2 Fenway Park – You can’t come to Boston and not see a Red Sox game at Fenway Park! It’s the oldest ballpark in the country and beloved for the green monster. Even if you’re not into baseball or sports at all, come to a game and sit in the bleachers, the energy and excitement of being in the crowds at the games is too fun to miss out on!
#3 Boston Public Garden – This was the nation’s first public arboretum, as it boasts a wide variety of trees. And it has since maintained its charm and fame for the Make Way for Ducklings statues, the swan boats on the pond, and the bench where that Good Will Hunting scene was shot. It’s my favorite park ever and if you come in the summer you’ll be treated to some beautiful garden displays!
What To Do
#1 Shopping on Newbury Street – This street stretches from the Boston Public Garden all the way down to Kenmore Square, passing the alphabet of streets from Arlington to Hereford. Starting at the garden you’ll see the first block or two is all high-end labels, but the rest of the way is a mix of major brands and independent boutiques and artist galleries and restaurants. I like to grab a cup of coffee on one end and then meander my way down street, seeing what new collections have arrived at all my favorite stores!
#2 The Freedom Trail – One of my absolute favorite things to do in Boston (even living there!) is the Freedom Trail, which is 2.5 miles of historic sites around the city. Boston was the starting point of the American Revolution and the first city to be settled, so we have more than a bit of history here. The Freedom Trail is denoted by a line of bricks in the pavement, with points of significance noted with a medallion on the path. It takes you past the Massachusetts State House, Boston Common, Old North Church, Paul Revere’s House, and more. You can walk it on your own or meet up with a guide who dresses and acts like he’s from the Revolutionary period.
#3 Sam Adams Brewery Tour – Head out the Sam Adams Brewery for a tour and tasting of our most famous and popular beer. This is also a sure-fire place to hear the Boston accent going on strong (it’s not as pervasive as the movies would suggest, but certain neighborhoods have it wicked good!). If you go on the last tour of the day, head down the street for your free beer at the super old and authentic Doyle’s Bar, and then hop on the party trolley where Jason takes you on a drunk tour of Boston. It’s the perfect way to unwind after a day full of regular tours!
Where To Eat
There are SO MANY great places to eat in Boston but here are a few of my favorites:
#1 Barcelona South End
A Spanish tapas bar where the great food is rivaled only by the impressive wine list. The vibe here is always good, as your surrounded by the happy chatter and laughter of people sharing a good meal together.Book Here
#2 La Dolce Vita
The North End in Boston is our version of Little Italy so you have a lot of great Italian restaurants to choose from but this one stands out on my list. Once you get there you’ll understand why…the old-as-dirt but sweet-as-a-cherub Italian man who owns the restaurant comes out and begins playing his accordion and singing classic Italian ballads. Crowds line up outside the open windows peering in with jealousy as you’re serenaded at your table by this old Italian charmer. I don’t think you could find a more authentic Italian moment anywhere, even in Italy.Book Here
#3 Barking Crab
#3 Barking Crab is the spot to get wicked good New England lobster! We love our lobster and have plenty of it, so come over to this little crab shack and join the crowds that amass for a taste of world-class seafood!Book Here
Where To Drink
#1 Clink at Liberty Hotel is one of my absolute favorite bars in Boston. This prison-turned-hotel has maintained the cool prison design elements while injecting a modern luxury appeal to the building. The bar draws a crowd of classy young professionals and is always a fun time, especially when the patio opens in summer.
Dress Code: Casual chic. No sandals (men), sneakers, baggies, sportswear, caps, sleeveless shirts (men) or shorts permitted
#2 The Intercontinental Hotel on the waterfront has a great patio bar open in the summer, and since it’s right next to the financial district, it’s a favorite spot for after work drinks. Drinks with a view? I’m in!
Dress Code: Casual chic.
#3 Eastern Standard is a consistently good bar, a classy alternative in the Fenway area, which is rather saturated with sports bars. I’m all for a good beer at a sports bar, but when you want a nice cocktail, this is the place to go.
Dress Code: Nice casual to dressy
Need To Know
It’s totally manageable to walk around in Boston, but you’ll sometimes want to take the T (subway) to get around quicker. So grab yourself a Charlie Card and top up. The T runs until midnight but bars are open until 2am, so you also have the option to use taxis or Uber, both of which are widely available. Boston is a really safe city and it’s easy to navigate. After a weekend here you’ll probably have a pretty good feel for the city but then each time you come back, you get the chance to further delve into new neighborhoods and explore the less-touristy sides of Boston!
With thanks to contributor ‘Brittany from Boston’. Brittany is a full-time traveler and professional travel blogger, making her way around the world and sharing the best of it with you! With a burning desire to see the world, she left behind her desk job and ordinary life for a life filled with adventure, and now she wants to show you that it’s possible to chase your own travel dreams. Get a dose of wanderlust and inspiration, as well as some practical travel advice and destination information, over at BrittanyfromBoston.com.