Boston City Guide
Breakfast & Brunch
So underrated. Best for a casual weekend breakfast with friends. Has a low key vibe in a great location inbetween Copley Square and other South End shopping.
Instead of going to a restaurant try the BPM. You’ll find Union Square Donuts, George Howell Coffee, Mother Juice, Swiss Bakers, Levend Bagelry and a ton more.
West End (Faneuil Hall Area)
An eclectic vibe of people and ambiance. My go to for a 'diner' type of breakfast. The long line goes fast, I promise. You can shop along Newbury Street while you wait.
Cute interior with yummy food. One location is much larger with seats and has a full kitchen. The other is a smaller joint with food to go.
A staple for Boston locals and tourists, because of their beautiful interior. It gets really busy almost every day, so the wait time can get long, especially in Beacon Hill.
Beacon Hill, Cambridge, Brookline, Fenway
Even though Black Bird Doughnuts in the South End are my favorite in town, if you’re in Somerville, these are a close second.
This is my favorite juice bar in Boston. They have the best juices, detoxes, acai/pitaya bowls and avocado toast.
Recently remodeled – it has a fun French vibe and great food. Try their bloody mary.
These are my favorite donuts in Boston! Make sure to get there early, since they tend to run out of customer favorites in the AM. There isn’t seating, so you have to take your items to go.
South End, Fenway
The best bagels in Boston. Get here early, because they close their doors when they sell out! FYI - this small place only has 4 tables, so seating can get tricky.
My favorite diner outside downtown Boston. A little bit out of the way for anyone who doesn’t live in the Allston area, but it’s worth the trek.
If you’re looking for somewhere a little fancier, this is your place. They also have a delicious ‘make your own’ bloody mary bar.
South End, Brookline
One of my favorite raw bars in the city. Try the lobster waffles and oysters for brunch while awing over the beautiful mosaic tiled bar.
They are known for their yummy burgers, but I love their breakfast sandwiches!
Downtown (Financial District)
Escape Boston for a hot minute and enjoy an awesome outdoor brunch with friends. Rotating specials and great drinks will keep you coming back.
Lunch & Dinner
Skip the main dishes and make a meal out of the small plates. Their back patio is beautiful and perfect for a spring, summer, or fall feast.
A little overpriced, but they have a great garden/outdoor area to enjoy some delicious seafood.
I love the ambiance of this place! It has a small cozy, yet fancy feel to it. It also has a great rotating wine selection.
Jon's favorite Italian restaurant in the North End. Make sure to check out the attached Italian take out market.
This place is a neighborhood fav. It’s always filled with a rowdy young crowd, which makes sense, because the drinks and apps are amaze.
South Boston ‘Southie’
Best tacos in Cambridge and don’t forget to try some tequila! Their sister restaurant is called Deep Ellum in Allston, which is also delish.
Like Coppa, Toro does small plates made to share, so make sure to come with lots of hungry friends. Reservations are a good idea.
One of the coolest places in China Town with a NYC kind of vibe. Try the pork belly steamed buns and their burger called the ‘Shojonator’. If they're full, try out their more laid back, sister restaurant called Big Litte Restaurant (BLR) around the corner.
For rustic and industrial ambiance, this is a great spot in across the bridge.
This small hipster spot has SUPER yummy food and a menu that’s constantly changing. It’s perfect for small groups or a date night. Try the chef’s poutine if you’re feeling adventurous.
Pabu is an Asian inspired bar and restaurant hidden on the second floor of the luxury high-rise, The Millennium Tower. Skip the pricey sushi; instead get sake and one of the amazing steak options.
One of my absolute favorites, because of it's dark moody atmosphere. They have amazing drinks (try their house-made tequila) and my favorite Mexican food in Boston. Also, you just can't go wrong with unlimited chips & salsa and complimentary cotton candy with pop-rocks!
Back Bay (Copley Square), Seaport
The names say it all. Drink is a great spot to grab a cocktail and is situated directly 1 level below the delicious Italian-inspired restaurant Sportello. And if you're looking for a night out afterwards (with live music) - go across the street for a good dive-bar kind-of-night at one of my favorite spots - Lucky's.
A must if you’re in the Fenway/Kenmore area. The oysters are delicioussss. Especially great for larger parties.
My favorite little Italian place in the South End. I love going a bit early and sitting outside on a nice summer day. You must get the meatballs.
I just love the ambiance of this place. Perfect location if you’re doing some Newbury Street shopping. Need a place with a similar vibe but more space? Head to Island Creek Oyster Bar in Fenway instead.
With a rotating menu every month, they serve all local ingredients. Sit at the chefs table!
One of my favorite restaurants in Somerville. Their food has a hearty yet modern feel to it and I love the open industrial floor plan.
I love the ambiance here. It’s large, but not too large. It’s fancy, but not too fancy. They have some semi-private rooms in the back for groups.
Financial District (Waterfont)
My favorite BBQ in Boston. Head chef Andy Husbands can't do any wrong. I always get the BBQ wing meal (extra crispy) with a side of corn bread and mac & cheese.
Cambridge & Seaport
This tiny, casual place has the best poutine in Boston. Their waffles are also amazeballs.
West End (Faneuil Hall)
Can’t beat their summer outdoor seating. The live jazz always makes for an entertaining night.
My favorite Italian restaurant in Boston and possibly my favorite restaurant in Boston period. Come hungry, because you must get the 3-course meal with the chocolate cake!
Such a pretty place in the newly developed Ink Block area. Definitely try out the tasting menu for a full range of flavors and make sure to get an affogato for desert!
This trendy asian fusion place is hidden in the Verge Hotel. It’s a little pricey so grab a drink and appetizers before heading out. Sit at the bar for fun views of the chefs in action.
I love how they freshen up the menu every month. Try the secret burger if you’re lucky enough to snag one (they only have a certain amount every night)!
All the things I love - food with Southern (New Orleans) influences, small plates and a raw bar all housed under a beautiful and cozy interior.
The BEST lobster roll you will ever have. Originally based in Portland, Maine I'm thanking my lucky stars I don't have to drive 2 hours to get here anymore.
Where casual, savory Asian meets fun Mexican. I love ordering in from this place for dinner - truth be told I've never been to the actual restaurant. Try the spicy pork tacos and the chicken poppers.
Have a big group? Or maybe your family is in town and you need a fancy-ish place to take them? This is your place! Great food, dark and moody atmosphere, perfect for a birthday or family celebration.
A few places I haven't had a chance to check out yet
Juliet, Prezza, O Ya, Bondir, 3 Little Figs, RUKA, Shepard, Fat Hen, Little Donkey, Moona, Ostra, Craig on Maine, Giulia, Uni, Wink and Nod, Capo, and Parla
Attached is the Lamplighter Brewery Co. and they serve Union Square Donuts.
Opened in August 2017, designed by a dear friend of mine. With gorgeous interiors, delicious coffee/tea, and yummy snacks including avocado toast, you'll want to stay and hang out here all day long.
Kendall Square, Cambridge
A relatively new coffee joint, adjacent to the Godfrey Hotel. I love their modern interior.
The best coffee shop in China town. The wine bar adds an extra element of fun.
A quaint shop near South Station that I like to go to before taking the train to NYC.
My go to spot when I’m shopping on Newbury St. I love their espressos!
Fort Point, Newbury Street
A favorite among Boston locals.
Along with their coffee, the food here is also great.
This Asian inspired place is a staple for locals who commute downtown for work.
Sights & Activities
A few super touristy things to do
Duck Tour, Freedom Trail, Faneuil Hall, Fenway Park, Paul Revere House, Swan Boats, Old North Church, Bunker Hill Monument, Newbury Street, New England Aquarium, Trinity Church & Harvard Square. Now that’s outta the way, here are my picks for best sights.
Constantly ranked one of the best museums in the US. If you have a Bank of America credit or debit card, you get in for free via the “Museums on Us” program that you’re automatically enrolled in. Just show your card at the front. More information on this program here.
Rent a kayak solo or with a friend for a relaxing afternoon on the water. If you’re lucky you might catch some Boston University sailors out and about.
Walk, run, rollerblade, bike (you get the idea) along Storrow Drive to see beautiful views of the Charles River and other locals hanging out on one of the piers. Walk across the Harvard Bridge and Longfellow Bridge for 360 views of the city.
Instead of paying $16 to go to the 50th floor Skydeck in the Prudential Tower, head up to the bar & restaurant on the 52nd floor for free and grab brunch, dinner or just a drink. The food might not be amazing, but the views are worth it.
Take in the Boston skyline at one of these rooftops
The Lookout Rooftop and Bar at the Envoy, Legal Harbourside, and The Sky Lounge at the Yotel all in Seaport. The Sinclair in Cambridge. And Coppersmith in Southie are a few that come to mind.
Catch a comedy show
Get in some good laughs at one of the theaters in Boston’s Theatre District (Wang Theatre & The Wilbur are my favorite). Laugh Boston in Seaport and Improv Asylum in the North End are also solid places to catch shows.
Find your favorite beach
Boston.com put together an amazing list of Boston’s best beaches. I love the beaches in the North Shore like Singing Beach in Manchester-by-the-Sea and pretty much any beach in Marblehead.
A favorite relaxing spot for Southie locals. There’s always beach volleyball and lots of twenty-somethings having a good time. Take a little bike ride along the ocean or grab a friend and play tennis at one of the free courts.
If you have a few extra days in Boston or you've already done all the touristy activities, spend a full day in Ptown - a wonderfully quirky town that sits at the very tip of Cape Cod.
Obviously this is a strictly summer activity, but still a great one. If you’re lucky enough to know someone who lives at the One Canal Apartments in the West End or The Ink Block Apartments in the South End, they also have great pools!
Very different than any other museum in Boston. The gorgeous garden brings people from all over the world and the eclectic collection of art is super special.
Spend 5 mins at the Boston Common then skip over to the Public Garden. In the summer the flower garden is beautiful and you’ll see lots of people sunbathing, taking pictures and playing ultimate frisbee. The Franklin Zoo park brings 2 swans to live in the pond during the summer months.
Hang out in Beacon Hill then head over to the Hatchshell (just cross the bridge over Storrow Drive) to check out a show or have a picnic. It’ll make for a perfect afternoon or date night. During the summer there are always fun events happening!
There are lots of companies that do this so I suggested comparing rates and reading reviews before you book. If you know someone who belongs to a club and can take you out privately, even better! If you’re more of a yacht person, that’s an option as well.
Being totally honest – when I did this with my mom in 2014 I thought it was going to be super lame, but it was SO much fun. Make sure to bring a sweater, because it gets really chilly (even in the summer).
There are a ton of great breweries in Boston, with Harpoon Brewery in Seaport being a favorite (probably because of it’s walkable location from downtown). Here’s Boston Magazine’s list of the top 21 breweries in New England.
SoWa showcases local artists, a farmers market, food trucks and a beer garden on Sundays in the summer!
Get out of the city for a day
Boston has a lot to offer, but one of the best things about it is it’s proximity to other New England cities. A few of my favorites are Portland ME, Newport RI, the White Mountains NH and Cape Cod MA, which are all ~2hrs away.
Get your North End sweet-tooth on
You’ve probably heard of the famous Mike’s Pastries in Boston’s North End (cannolis anyone?), but the locals actually go to Modern Pastry and Bovas. Might as well try all three and pick your favorite!