Boston Weekend Getaway: What to Do, Where to Stay & Travel Tips
Planning a girls trip this fall? Put Boston at the top of that list. Trust me. I just went to visit my friend here, and every time I told people I was heading to Boston, the response was always the same: “omg you’re going to love it there!”
It’s historic, picture-perfect for your Instagram feed, and has some of the best food. Plus it’s easy to get to. From cobblestone streets and speakeasies to boutique hotels and trendy restaurants, Boston has a little something for every type of traveler. And I’m gong to tell you about it.
Here’s everything you need to plan the ultimate weekend in Boston.
how to get there:
Flying into Boston Logan International is the best way to get here. It’s super close to downtown - about a 15 min drive.
how to get around:
One thing to know: don’t rent a car. Parking here is outrageously expensive and not worth the stress. Boston is incredibly easy to navigate with public transit and rideshares.
The T (Subway): Affordable, fast, and connects most neighborhoods.
Ferries: Fun and scenic! The ferry links downtown Boston with Charlestown, East Boston, and the Harbor Islands.
Walking: Boston is one of the most walkable cities in the U.S.—perfect for exploring with your girlfriends.
Biking: The Bluebikes program is everywhere if you want a more active way to get around.
Uber/Lyft: Always an option, especially for nights out.
where to stay:
Every neighborhood here has its own vibe. So it really depends on what you want to do. My friend lived in East Boston (Eastie) so we stayed there and I probably wouldn’t recommend it if you want to do more touristy things.
Back Bay – Chic, central, and walkable
Beacon Hill – Historic and picture-perfect
Downtown/Theater District – Convenient for sightseeing
South End - For the foodies
NEED SOME OUTFIT INSPO?? CHECK OUT WHAT I WORE IN BOSTON
GO ON A FOOD TOUR
One of my favorite things to do in every city is to go on a food tour. It’s a great way to get to know the city you’re visiting, learn some historical information, and of course, eat some delicious food! We booked a tour through Bites of Boston - a women-owned and led small business focused solely on the food scene in Boston.
There are 4 different tours to choose from. We choose the classic downtown Boston - eating Boston beans, clam chowder, lobster rolls, and Boston cream pie. Our tour guide informed us about how these staples came to life and the history behind them. She also had amazing recs on where to eat for the rest of the trip too. 10/10 recommend!
SHOP ON NEWBURY STREET
Known as Boston’s “Rodeo Drive,” Newbury Street is one of the city’s most popular shopping streets. The eight-block stretch is filled with everything from designer boutiques like Chanel and Burberry to local shops, vintage stores, and endless coffee spots. If anything, it’s good people watching and window-shopping.
VISIT FENWAY PARK
Even if you don’t like baseball, visiting Fenway Park is a bucket-list Boston item. If you’re there during baseball season, you should absolutely go to a game, eat a hot dog, and take a picture in front of the park. Baseball fanatic? Take a tour! There’s tons of bars near Fenway so you can also take yourself on a pub crawl around the park!
EAT ALL THE FOOD!
Boston’s dining scene is one of the best in New England, and a girls weekend is the perfect excuse to eat at the best spots. Here are some must-try restaurants:
Anywhere in North End – This is the Italian district of Boston so you can find the spot that speaks to you. Here are a few: Carmelina’s where you can find house-made pasta; Mamma Maria has a uniquely homey atmosphere and perfectly romantic for a girls night; Little Sage is a new hotspot with a creative lobster and dandelion gnocchi; Lucia has a perfect outdoor patio for summer/fall nights and very old-school; and Red Fox is a moody, intimate spot with a cacio e pepe martini.
Neptune Oyster (North End) – A Boston classic for seafood and lobster rolls.
SRV (South End) – A Venetian-style wine bar with incredible cicchetti (small plates) and pastas.
The Elephant Walk (South End) – What started as a food truck but is now a restaurant, this Cambodian-French fusion spot has so many flavorful dishes. Try the traditional spring rolls, the ribs, and the shrimp curry.
Amar (Downtown) – Boston has one of the biggest Portuguese populations so this is a must try for elevated seafood dishes.
Saltie Girl (Back Bay) – This raw bar is all the rage, especially after a day of shopping.
Rino’s (East Boston) – If you want big portions, this is your spot. Get the lobster ravioli but it’s cash only!!
If you need more, choose one from this best restaurants in Boston list and you can’t go wrong!
WALK THE FREEDOM TRAIL
The Freedom Trail is a 2.5-mile path that winds through 16 of Boston’s most historic landmarks, including Paul Revere’s House, Burial Grounds for patriots like Sam Adams, Old North Church, Benjamin Franklin statue, you get to see where Charles Ponzi operated and got called out, the Old Corner Bookstore, and more. Walking the trail is one of the best free things to do in Boston. You can see as much or little as you want and stop for coffee and food along the way.
GO TO A COMEDY SHOW
The comedy scene is solid in Boston. So if you love to laugh, grab tickets to a comedy show. Laugh Boston in the Seaport District is one of the most popular venues, hosting both big-name acts and local comedians. If you like something more like SNL (sketch or imrov), there’s endless options to choose from. We went to Lil Chuck Boston and had the time of our lives - they really involve the audience which is super fun!
GRAB COCKTAILS AT A SPEAKEASY
Boston has no shortage of speakeasies thanks to the Prohibition era. So if you love a craft cocktail, be sure to check them out!
The Wig Shop: This was my favorite! The ambiance was really my vibe and they made a great pickle dirty martini.
Backbar: A cozy, tucked-away gem with creative cocktails.
Offsuit: A tiny speakeasy with a constantly changing menu—finding the entrance is part of the fun (hint: it’s in the alley).
Drink: Famous for not having a menu—bartenders create custom cocktails based on your taste preferences.
These intimate spots are perfect for starting or ending your night out.
VINTAGE SHOPPING IN CAMBRIDGE
Just across the Charles River, Cambridge has some of the best vintage and thrift shopping near Boston. Head to The Garment District, a massive warehouse offering everything from designer pieces to funky costumes. You never know what treasure you’ll find, and it’s a fun way to spend an afternoon before dinner or drinks.
STOP BY THE BOSTON LIBRARY
The Boston Public Library is so much more than a library—it’s an architectural masterpiece and be prepared to want to take pictures everywhere you turn. The outdoor courtyard is straight out of a movie and did I mention it’s FREE. If I lived here, I would come work and read here all the time. Be sure to admire the marble staircases, murals, and the reading rooms where everyone is studying. It’s a quiet, beautiful escape right in the middle of Back Bay.
CHECK OUT THE MUSEUMS
Boston is home to world-class museums that are perfect for a rainy afternoon or if museums are your thing:
Museum of Fine Arts (MFA): One of the largest art museums in the country, featuring works from ancient Egypt to contemporary artists.
Isabella Stewart Gardner Museum: A Venetian-style palace filled with art and lush gardens, plus the site of the famous unsolved art heist worth $500 million (pictured above). The art has never been discovered so go check out the empty frames.
Institute of Contemporary Art (ICA): A sleek, modern building on the waterfront with thought-provoking exhibits and amazing harbor views.
Boston is the perfect mix of history, food, and fun—making it such a great choice for a girls weekend getaway. If you can, feel free to sneak away to Salem during the fall!
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