Girls weekend in Boston? Sign me up. My first trip to the city was in the summer of 2015 and I just wrapped up my second visit as part of a week-long road trip Jackie and I did up the East Coast (more on that coming in a future post!). We had two other friends join us for the Boston portion and it was such a blast. Full disclosure: it was BLAZING hot the few days we were there and we didn’t get to do quite as much as we’d wanted but we still hit a lot of the highlights. I have suggestions of other activities at the end of this post in case you have more time there and if you’d rather just reference a list of things, check out my Boston destination page.
Without further adieu, here’s how we spent 3 days in Boston:
FRIDAY
Left NYC around 9:30 AM and arrived in Boston by 1 PM. Checked into our hotel, the Boston Park Plaza, and went straight to a late lunch. The hotel was the perfect place to stay as it felt really central to all the things we wanted to do (both walking and grabbing a quick Lyft). I found the Banks Fish House on a Boston Eater list and it did not disappoint. The décor was stunning and the food was really delicious. With 4 people we were able to order a ton of things: fried artichokes, unicorn oysters, steamed mussels, lobster roll, chowda flatbread.
From there we wandered down part of Newbury Street into the Public Gardens and to the historic Beacon Hill neighborhood. After popping into some vintage shops, snapping pics on Acorn Street and grabbing a pick me up from Tatte, we went back to our hotel to change for dinner. We took a Lyft over to Bar Mezzana which came as a recommendation from Claudiane of @nailthecocktail. We ordered all the things and left with happy, extremely full bellies: focaccia with peperonata, white bean puree, eggplant w/chili dips; prosciutto; black truffle burrata; orecchiette pasta w/sausage, fennel, radicchio; paccheri pasta w/a deshelled one and a quarter pound lobster served with lobster crema, green onion, and tomato.
SATURDAY
We were up fairly early for some photos and then swung by Tatte for a light breakfast. Tatte quickly became our favorite coffee shop and we’re all trying to manifest them opening a Westchester or NYC location. Things to get at Tatte: the Jerusalem bagel, pistachio dounut and a pistachio croissant.
After Tatte we strolled down Boylston to Washington Street toward State Street to check out the more historic part of the city. You can also head toward the Massachusetts State House which is the start of the Freedom Trail, but since we did the park the day before we stuck to the streets. We wandered through Faneuil Hall and Quincy Market (think food hall) and then walked East along the water toward the new Seaport neighborhood. Our original plan was to go to the North End from there, but we had a brunch reservation to catch so we pivoted a little.
Brunch was at Woods Hill Pier 4 and the things not to miss on the menu are: WHP4 burger, salad of mixed greens, heirloom tomato salad (yes, I’m recommending salads because they were THAT delish!) and the lobster popover.
From there we went back to the North End for some cannolis. Mike’s Pastry is known as the tourist favorite for cannolis and Modern Pastry is more the locals favorite so we decided to do a taste test. We got ricotta and pistachio at both and while both were delicious, we felt like Mike’s won because the filling was a little more flavorful and the shell was crunchier. (something to note: Mike’s cannolis are huge so if you want to try multiple flavors go with a group or prepare to have leftovers!)
Totally exhausted from the heat, we went back to the hotel to chill before dinner. Dinner was at Saltie Girl and it was honestly one of my favorite meals of the trip. Things you MUST order: steak tartare, snow crab toast, torched salmon belly, warm spicy crab roll and the rock crab carbonara.
We also had the ginger scallion lobster and coconut cream cake which were good but not amazing like the other dishes. We had a night cap back at hotel and it was off to bed (anyone else like a good hotel bar drink?).
SUNDAY
We got packed up to check out and hit up Tatte (yes, again) and I had really wanted to check out the Boston Public Library courtyard but it’s closed on Sundays. We went back to the Seaport area for brunch at Lolita (the Fort Point location) and it was yet another amazing meal. Make sure you get the: guacamole fresco, spicy artichoke empanadas, tuna maracuya, lolita lobster roll, mushroom quesadilla and broken eggs, and for drinks get the Lolita, Diablo and Spicy Cucumber.
From there, Jackie and I made our way further north and Simone and Tiffany headed back to NY.
I highly suggest making reservations at all the restaurants we went to because they were very busy (Saltie Girl was a late dinner because we waited too long to book and couldn’t get a prime reservation time) and for good reason.
While we did a lot of eating and drinking during this trip, there are a ton of other things to do in Boston including:
- Catch a Red Sox game at Fenway (we did this in 2015 and it was a blast!)
- Walk/shop along Newbury Street
- Explore Cambridge (across the river where Harvard and MIT are – we still didn’t make it on this trip but it will be at the top of my list when I go back!)
- Visit the Isabella Stuart Gardner Museum
Some recommendations we weren’t able to squeeze in:
- Beehive for Brunch (I went on my first trip to Boston and I remember it being super good!)
- Bootleg Special – seafood and crab boils with Mardi Gras inspired cocktails
- Committee – cocktails and Greek food
- Coppa – charcuterie boards
- Flour bakery (this was on a ton of guide lists and they have a couple locations – one of my IG followers suggested the Kouign-amann)
- Legal Harborside
- Lookout Rooftop
- Mariel – Cuban food and drinks
- Neptune OysterPammy’s – small plates
- Pink TacoRow 34 – oysters and a lobster roll
- Source for pizza
- South End Open Market (also went on my first trip, specifically for a donut stand)
- The Tall Ship Boston and ReelHouse (both in East Boston, ReelHouse has views of the city)
- Yellow Door Taqueria – tacos and margaritas
Have you been to Boston yet? Drop a comment below if I’m missing anything! I really enjoyed this trip and while we did touristy things, it also felt pretty chill and I appreciated we took time to just wander. I’d really love to go back when the leaves change in the fall because all the photos look gorgeous!
PIN this guide for your next trip!
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