The Greater Boston area is the home of famous breweries like: Sam Adams, Harpoon Brewery, Trillium Brewery, Lamplighter, and Aeronaut … It’s also — surprise, surprise — chock full of Irish bars! However, though I do enjoy a good pint now and then, cocktails and wine will always steal my heart. So, here is my list of favorite watering holes in Boston as of 2019!

Also check out: Where to Eat in Boston and Favorite Cafes and Bakeries in Boston!

Update (7/2/2020): I’m so sad to see some of my favorite restaurants in Boston closing like Deep Ellum, Eastern Standard, and Cuchi Cuchi. Read this Boston Herald article for a list of closings.

Eastern Standard

Bar/Restaurant in Kenmore Square, Boston

Update (7/2/2020): Unfortunately due to the COVID-19 crisis, Eastern Standard closed its doors permanently.

Located in Kenmore Square, Eastern Standard feels like an oasis in a sea of sports bars. Sibling restaurants, Island Creek Oyster Bar and the Hawthorne Bar are right next door for easy access — all brought to you by restauranteur, Garrett Harker, and bar director, Jackson Cannon.

I’m not ashamed to admit that I’ve been on many a date here! The food was solid but not impressive. I did however really loved sitting at the bar, snacking on small plates, and imbibing wine and far too many delicious cocktails!

USA Today named Eastern Standard one of the country’s Top 10 Hotel Bars and Boston Magazine awarded it Best Restaurant Bar in 2006 and Esquire magazine included it in its 2008 list of Best Bars in America.

Star Chefs

The Hawthorne

Bar in Kenmore Square, Boston

For serious cocktail enthusiasts, this low-key bar provides everything you need: small bites and fantastic drinks — made from award-winning bartenders who really know what they’re doing.

Warm and comfortable with low tables and plenty of armchairs, drinking at The Hawthorne is almost like sitting in someone’s living room, except you’re sipping on exceptional drinks like the Air Mail (a champagne cocktail with white rum, honey, lime and bitters) and small bites like deviled eggs with crispy prosciutto, pickled anchovy, and chorizo toast.

The Thrillist

A4cade Bar

Bar in Central Square, Cambridge

Frequented by many MIT students and arcade-game lovers! The drinks are geeky and fun. It’s also a speakeasy at the back of Roxy’s Grilled Cheese (Central Square location), so feel free to pop out and get some snacks if you’re feeling late-night munchies.


One of my good friends once texted me after a night out at A4cade, “don’t fuck with the slushie.” Those alcoholic slushies were delicious, but please limit one to two per person maximum or you’ll end up blacking out like I may or may not have done before … There were also flaming shots involved before they stopped those shenanigans.

Deep Ellum

Restaurant and Bar in Allston

Update (7/2/2020): Unfortunately due to the COVID-19 crisis, Deep Ellum closed its doors permanently, and Lone Star (its sister restaurant) will take its place.

If you somehow end up deep in Allston and are pining for a good cocktail, this is where to go. In the summer, we’d end up on the patio for brunch, nursing our hangovers with Bloody Marys and Truffle Gorgonzola Fries. Reminded me of nights at Yaffa Cafe (now closed) on St. Marks in the Village, New York City.

I’m also a big fan of Lone Star Taco Bar, especially their grilled street corn! Though if you’re searching for authentic tacos in Boston, Taquería Jalisco in East Boston is where it’s at.

Trina’s Starlight Lounge

Bar and Restaurant in Inman Square, Cambridge

I wasn’t crazy about dining here, but I sure loved the chill, fun atmosphere and drinks in the evenings. Serving chicken & waffles and cornbread, you may also want to come back for brunch!

Brick & Mortar

Bar in Central Square, Cambridge

What to order at Brick & Mortar?

I’m a big fan of mezcal, so I’m keen on their ‘naked lunch’, made with mezcal, lillet, yellow chartreuse, grapefruit and tiki bitters.

Model Cafe

Bar in Allston

Oh goodness gracious, this place. Expect a very simple, cash-only bar, and don’t get overly fussy with drink orders. You’re here for the dark, lively atmosphere, the company, and the cheap drinks.

I spent a good chunk of my early 20s lurking in dark corners of this hole-in-the-wall bar where you’d meet literally all sorts — band groupies, musicians, artists, maybe your old English professor. I went here so much that I’d skip the line out front, and my friends would smuggle me in through the back door. Friends would usually hit up the Silhouette Lounge for pitchers of beer and darts then walk over to the Model where the music was anywhere from ‘Vogue’ to ‘We Will Rock You’.

What to drink at the Model Cafe?

Do as the locals, and order a Pabst Blue Ribbon. You’re here for the atmosphere and cheap drinks! Don’t order anything too complicated. There is wine if you ask for it — you’ll be asked “red or white?” — but I’m likely the only person who has ever asked for it.


Go early on a weekend or you’ll never make it through the line! It’s cash-only, but there’s an ATM inside.




For a goooood time, call Yvonne. A romantic speakeasy bar/restaurant in the heart of Downtown Crossing. Great for groups, dates, or flirting at the bar.

Explore the different rooms in Yvonne’s, including a library bar filled to the brim with books — often seen scribbled by mischievous guests. The main dining room is ornate with candlelit, white tablecloth tables, plush sofas, chandeliers, and the original Locke-Ober wood bar — helmed by highly-skilled bartenders.

Chefs, Juan Pedrosa and Tom Berry, have created an eclectic, delicious menu of small and large plates that are meant to be shared.

Put on your reading glasses, sip an espresso martini, and sit by the fire in their super sexy library bar or wander down to the chandelier-filled dining room to mingle with party-mood guests.

What to drink at Yvonne’s?

Favorite cocktails: Penicillin, 1975, Grande Dame, Rubicon, Espresso Martini, large format Moscow Mule. 

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