Sometimes you just need a change of scenery, a good friend (in this case, my cousin Susie), and a city with enough energy to keep the laughs flowing well past midnight. For me, that city is Boston. Living in Florida, I was missing the cooler weather, and this summer I found myself going up multiple times. But instead of doing the predictable routine of staying in the South End or Back Bay, shopping on Newbury (not that we didn’t go there), we decided to shake things up this time. We gave our girlfriend getaway a Southie twist, and I’m so happy that we did.
South Boston, lovingly called “Southie” by locals, isn’t the gritty neighborhood your grandparents warned you about (and it’s not the South End where you’ll usually find me). Today, it’s one of Boston’s hottest areas, where tradition meets trendy, where Irish pubs live side by side with rooftop cocktail bars, and where the vibe is a little less polished than Beacon Hill but ten times more fun. If you’ve never thought of Southie as your home base for a girls’ weekend, you’re definitely missing out.
Why Southie?
Boston has a lot of neighborhoods with personality, but Southie has attitude. It’s walkable, it’s edgy, and it’s packed with a mix of locals who’ve been there forever and new residents who’ve turned old brick warehouses into stylish living spaces. It’s where young professionals hang out, where families still gather for Sunday dinners, and where you’ll find some of the best nightlife in the city.
For girlfriends traveling together, Southie has everything you need: great food, fantastic views of the skyline and harbor, and plenty of character. Plus, it’s close enough to downtown Boston that you can still hit all the classics – Fenway, Faneuil Hall, and the Freedom Trail but with the bonus of coming back to a neighborhood that feels a little more local, a little less touristy.
Where We Stayed
Forget the predictable hotel chains. For this getaway, we wanted something modern, stylish, and easy to get everywhere from – the Cambria Hotel Boston Downtown–Seaport. I’ll be honest, I wasn’t sure what to expect. I’ve stayed at plenty of hotels that call themselves “boutique” or “chic,” only to walk into a lobby that feels sterile or a room that makes you want to leave it as quickly as possible. Not here. From the moment we stepped into the lobby, you could feel the difference. It’s light and airy, and the desk staff are less stiff than the usual Boston hotels and more willing to help you find the best places to eat, visit, and more. I even got the woman at the desk to tell me her favorite neighborhood lunch spot (yes, it was great) and how to get just about anywhere we needed to. It helped that the “T” station is directly across the street, but so much was also walkable.
I hadn’t stayed at a Cambria before (yes, I was a newbie) and found it to be chic without being fussy. The vibe is modern, but it doesn’t scream “look at me.” It feels effortless, you know, kind of like stylish in the way your friend who always knows how to put together the perfect outfit is stylish.
The lobby has comfortable modern seating to relax and wait for friends (or in my case, for my brother to wait for me to show up from getting ready in my room), there’s a small convenience area with chips, chocolate, drinks, and snacks should you have a snack attack, and the Essex Restaurant (open for breakfast and dinner) are all on first floor.
With renowned Chef Polit Castillo in the kitchen, you’ll find globally inspired small plates as well as full-on entrees. I checked out the menu, but unfortunately had other plans, so I’ll wait until I’m in town next time to bring you all of the restaurant details.
Right off the bat, the room blew me away. For once, we actually wanted to spend time there. We lucked out with a corner suite, and when Cambria says “suite,” they mean it. This isn’t one of those glorified “bigger rooms” with a sofa shoved into the corner. No, it’s the real deal: two distinct spaces, one for lounging and one for sleeping. Spacious, airy, and we had the most incredible sweeping views of the Boston skyline, the kind that make you stop, mid-conversation, just to stare.
The rooms are equipped with a mini fridge, microwave, and safe as well as a stocked Keurig and plenty of outlets, USB ports, and one of the largest TVs I’ve ever seen in a hotel room. They also have a fitness center, but with all of the walking we did in the city, we never had to use it.
Each evening, we were reminded with a Thoreau quote over the bed to “Aim above morality. Be not simply good: be good for something.” I loved waking up to the city stretching out in front of me, the light spilling through those big floor-to-ceiling windows. It felt energizing, like the city itself was inviting us to come out and play.
The Rooftop Ritual
But let me tell you about the highlight: the rooftop bar, which is part of the Essex Restaurant (so, yes, you can order food as well as drinks).
This is where you’ll want to hang out for sure. Grab a cocktail from the bar and head to a comfy seat (there are sofas and chairs that are large, soft, and curl-up-able), Because I was there in summer, the entire rooftop was a garden with hibiscus and clematis separating each section, offering privacy yet open to the Boston skyline twinkling below. I love rituals, even when I travel, and this is the perfect ritual to set the tone for the evening, whether you’re planning on going out, coming back from dinner, or just want to “stay in” for the evening. There’s something about being above it all, city lights stretched in every direction, that makes the night feel full of possibility.
It isn’t just about the drinks (though they are excellent). It is more about the atmosphere that makes it feel like a REAL girlfriend getaway (gardens paired with a glass of wine tend to do that).
If the room was where we recharged, the rooftop is where we celebrated.
Day One: Rooftops, Southie Flavor & Local Classics
After checking in and clinking glasses on the rooftop, we decided to start our trip with a little Boston history—and some seriously good food—at Amrheins. If you know, you know (IFYKYK). This Southie staple has been around since 1890 and still serves up some of the most authentic bar food in the city, with a waitstaff that feels very BOSTON. From the rich clam chowder to the perfectly crispy fish and chips, it’s comfort food with a side of tradition.
Not only is it the oldest bar in South Boston, but the actual bar itself is the oldest hand-carved bar in America. Since museums were not on the agenda for this trip, we’ll call this our little bit of history for the trip.
Still in Southie, we did what girlfriends do best: wandered into spots that caught our eye, laughed too loudly, and met up with friends for dinner.
Day Two: Markets, Music, and Fenway Magic
The Cambria is perfectly located with the T right across the street, so we jumped on and headed to the Time Out Market for a food hall adventure. Picture a collection of some of Boston’s best chefs under one roof, who happen to be perfect for friends with very different cravings. My cousin told me about a pair of James Beard award-winning chefs at Ms. Clucks Deluxe Chicken & Dumplings, so this is exactly where we BOTH headed.
We ordered the Smash Dumplings and a bowl of their Signature Spicy Chicken & Dumplings Ramen, and went back and forth tasting (or should I say devouring) both. Portions are generous and the prices are typical of food hall food (less expensive than I would have imagined, with the dumplings at $10 and the ramen $17).
That night was one for the books. I had scored a pair of tickets to see James Taylor at MGM Music Hall at Fenway. If you’ve ever loved James Taylor and honestly, who hasn’t? You know how nostalgic it feels to hear “Sweet Baby James” live. Oh, and I thought I was buying first balcony side (having never been to this venue before), but nope – we had front row side (just steps away from the stage).
Walking from the food halls over to Fenway, with the buzz of Sox fans and the hum of excitement in the air, felt like stepping back in time. From the food hall to the venue, we had to walk by the ballpark before the show, soaking in the energy of one of the most beautiful baseball parks in America, with its iconic green and red details glowing under the evening lights.
The music, the walk, the atmosphere—it was pure Boston magic.
Day Three: Shopping Sprees, Cafés & A Sweet Send-Off
No girls’ trip is complete without a little retail therapy, so we made our way to the Prudential Center. The Pru is a shopping playground with everything from luxury boutiques to favorite go-tos, and the perfect place to pick up a little something to remember the trip by.
I happened to be walking by Vineyard Vines and saw this sweater in the window, so I HAD to buy it!
Of course, shopping works up an appetite, so we made it a point to stop into Tatte Bakery & Café, a personal obsession of mine. Truthfully, I can’t come to Boston without at least one (okay, maybe daily) stop at Tatte. The pastries are flaky dreams, the coffee drinks perfect, and the vibe is cozy yet chic in that effortlessly Boston way. It’s also a favorite lunch stop of mine!!
We lingered there, laughing over cappuccinos, before strolling back through the city one last time. We had gotten exactly what we wanted: a mix of local flavor, new adventures, and the kind of shared memories that will make us smile long after we’re home.
The Southie Twist
What made this girlfriend getaway so special wasn’t just the time with friends (though that’s always the best part). It was that we got to experience Boston through a different lens. Southie gave us tradition at Amrheins, fun at the rooftop bars, easy access by public transportation to food halls and Fenway magic, and enough character to keep us talking about it the whole way home.
Boston will always be a city full of history and tradition, but in Southie, we found a version of it that felt made for us. Edgy, delicious, stylish, and filled with laughter, it was the ultimate girls’ trip.
So, if you’re planning your next girlfriend getaway, skip the predictable. Head to Boston. Stay in Southie. And get ready for a girls’ weekend you’ll never forget.
- Start by making your reservation at the Cambria Hotel Boston Downtown–Seaport
