Boston Guide
Chunky cashmeres. Watercolor trees. Teeny coffees. Swirly breezes.
4:30 sunsets. Bistro lights mandatory.
I haven’t been to New England since I was 7 and my parents and I road tripped through several states lily pad hopping from one charming bed & breakfast to the next while chasing the changing of the leaves (see my Fall Foliage Bucket List here).
Returning for a 4-night visit for what felt like my first time in the city (sorry Mom & Dad, I don’t remember much!), I wanted to explore, see, and taste as much as possible.
Below is a list of activities and restaurants I would absolutely recommend to a friend as well a long list of all the recommendations that poured in over IG DMs (thank you, as always!)
Come along with me to boston…
What To Do
Isabella Gardner Museum
Lived up to every bit of its enchanted Italian garden meets artist getaway hype. 100% would recommend if you find yourself in Boston ✨
AND !!! — Don’t forget your AirPods because their artists walk throughs you can access via their website of the otherwise entirely unmarked pieces (by Isabella’s original 1900s design/desire to have it be an emotional & individual experience unlike other information packed museums) are so smart & fun.
It feels like a being in a college elective with the professor everyone loves!
Walk down Marlborough Street while listening to jazz
This street is DREAMS! Every other corner of Boston feels special and ancient and gorgeous (so I really didn’t understand why THIS street should specifically be walked down.)
I made my way to the Back Bay, plugged in a Billie Holiday station on Spotify, began to walk, and OH MY GOODNESS MAGIC. It was a brick meets flurry of orange leaf wonderland.
Pop into shops along Newbury Street
All the mainstream goodies and Boston only boutiques too! I really enjoyed a cup of coffee from The Thinking Cup.
A friend said:
“To go to Ball and Buck for a little Texas meets city...cool menswear shop; otherwise every cutesy preppy store ever is here!”
Check out Acorn Street
Allegedly the most photographed street in Boston. The cobblestones are HUGE – think softballs lining the street.
Explore Beacon Hill & Back Bay
Mozy through the neighborhoods and then pop over to walk through the Boston Commons – like Central Park for Boston. So so gorgeous, especially at sunset!
Watch the sunset at near the bridge of the Boston public garden
Bring bread for the swans and a bottle of wine for yourself! Fingers crossed for the cute live musicians are there for you that were there during my visit (vocal chords of butter!)
Walk the Freedom Trail
I’m a nerd so this is the ultimate way to spend a morning in my book! Follow the red brick road inlaid in the sidewalks winding all through the city.
I found a podcast (linked below) which told the history of each stop and played period appropriate music in while you walk to the next stop. LOVE. IT.
What I Couldn’t Get To & Will Do Next Time!
+ Boston Public Library
*Closed due to COVID
+ Take the ferry from the airport into town
*Also closed with COVID, but I’ve heard it’s the ONLY way to arrive to the city on a crisp fall day!
+ Take the ferry to Salem for the day (and do the Hocus Pocus tour!)
+ Walk around Harvard’s campus (hello, Elle Woods things!)
Where I Ate
Lolita
If Dia de Los Muertos was a restaurant.
Their bread basket is literally a tequila snow cone smoking out of a silver cauldron. They have their own tequila label (tangy!). Be prepared for SPICY food (I was a total baby lol). And get excited for the periwinkle massive fairy floss that comes with the check.
Go to the Fort Port location over the Back Bay location if you can!
Citrus & Salt
Mexican tapas with fun flavors (think Hot Cheetos crusted street corn) and hysterical drink names –– “Well Shit, What Are Y’all Doing?” // “I Didn’t Text You, Tequila Did” // “Tequila Is Cheaper Than Therapy” // “Becky Juice” // “Tequila Take The Wheel
Buttermilk & Bourbon
A Louisiana concept that is so so fun inside! Each room is different and detailed. Voodoo lounge is vibey and a little scary lol.
Panza – North End
North End is Boston’s Little Italy. Peep into window and you’ll see fresh pasta being made at a Speedy Gonzalez rate and red wine flowing. My favorite part — the little old men dotting every other street corner shooting the breeze in Italian.
Durty Nelly’s
The diviest of dive bars. I honestly felt like they had paid actors in there (like pilgrim actors when you visit Williamsburg or something) because the convos and Boston accents were NOT REAL LIFE LOL.
Mike’s Pastries
For their famous cannolis!
*Cash only
(NOTE: I unfortunately couldn’t indulge because of my nut allergy… it’s a cross contamination nightmare. BUT my friend very much enjoyed the “cream filled taco thing” 😂!)
Your Recommendations:
+ Ride a blue city bike along the Charles
+ The Improv Asylum in the north end!
Hilarious! Quick, cheap comedy shows (perf chill Saturday afternoon!)
+ Tatte
Go to the Beacon Hill location for brunch or a coffee (*be prepared for a line… it’s worth it!)
+ Quincey Market near Faneuil Hall
+ South End Buttery
+ Flour
+ Oishi (sushi)
+ Committee (Mediterranean)
+ Lola 42
+ Coppa
+ Row 42 (really good lobster rolls)
+ FRENCHIE
+ B&G Oysters
+ Yvonne’s
Speakeasy and home to a friend’s favorite drink menu in the city (*has cool library bar & a chandelier room through a hair salon)
+ Bee Hive (live jazz music and great cocktails)
+ Yotel (rooftop deck of hotel)
+ Envoy/outlook kitchen (rooftop hotel)
+ Lions Tail
+ 30 Germania St
+ Fairmont hotel
+ Stephanie’s
+ Atlantic Fish
+ Summer Shack
+ Exodus bagels
+ Barking Crab
+ Eataly
+ Top of the hub
*Really amazing view!
+ Figs
+ Omni
(Get the Boston cream pie!)
+ Artu Boston
+ Paris Creperie
+ Publico Boston - rooftop bar
For more recs…
Twist of Lemons Guide has a great city guide that I purchased (especially if you’re moving there! It has great advice about what it’s like living in each neighborhood, commute pointers, etc!) See here.