The Coolest Bars in Boston

Like my parents, I love a good happy hour special. Unfortunately, Massachusetts doesn’t do happy hour. It’s illegal. But that won’t deter me from enjoying after-work cocktails with my friends. Living downtown gives me access to some of the best bars in Boston, and this summer, I’ve discovered some new and wonderful places to decompress at the end of the day. 

TASTE WINE BAR & CAFE

Located at 101 Summer St. near South Station and Downtown Crossing, Taste Wine Bar & Cafe‘s grand opening was on Aug. 21. I got a sneak preview thanks to my friend Kerri, who has gotten to know the owner through their sister store, Common Vines Wine Shop. With clean white design, an exposed brick wall, and trendy lighting, it’s an Instagrammer’s dream. Taste offers an extensive wine-by-the-glass menu, a delectable small plates selection and wine tasting seminars. They describe themselves as “an urban tasting room with education, a place for people who enjoy wine, beer and cheese to hang out.”

During a preview event of this Boston bar last week, I sampled things like a mushroom and brie toast, and ricotta toast, a fig and blue cheese flatbread, and Korean meatballs. The wine offerings were extensive and all unique and interesting (without being too obscure). My favorite of the evening was a sparkling red wine, Lini Rosso Lambrusco. Served chilled, it was a welcome surprise. I ended the night by buying a bottle at the wine shop.

Pro tip: The wine shop has free daily tastings and a rewards program for frequent flyers. 

ENVOY HOTEL & YOTEL BOSTON ROOFTOP BARS  

Nothing says summer sophistication quite like a rooftop bar in Boston. The Envoy Hotel and the Yotel Boston sit diagonal from each other in the Seaport neighborhood. 

The Envoy Hotel’s Lookout Bar has views of the water and is very popular destination for men in button down shirts and dress pants, and women in wrap dresses and heels. If you come for happy hour, you may have to wait in line outside the hotel to be let up. Then, once you get up there, you may find parts of the deck blocked off for private events like we did. The drinks weren’t any more expensive than most upscale bars in the area, but it did feel a bit overcrowded when we were there. I’d recommend trying to get up there before 5 p.m. and on an off day. All in all, a fun place to stop in at least once during the summer, but you should know you’re going to a very popular destination.

The Yotel Boston’s rooftop bar is new as is the hotel. While it doesn’t have an ocean view, the skyline sits in the background and the roof deck has plenty of seating space, ensuring you don’t have to stand around in heels all night. Like the Envoy Hotel, you may have to wait before getting up to the rooftop, but there’s a bar downstairs where you can relax until space clears. Once you get to the penthouse space, you have the option to sit inside on some couches or at the bar. Of course, the goal is to get out to the terrace.

Here’s what you should know: If the terrace is full, you’ll have to wait for a spot even if you’re already in the penthouse. The upside is that when you get a spot outside, you’ll have a seat. I think that’s worth it especially if you plan to linger like we did. 

NORTH SQUARE OYSTER

North Square Oyster is a new gem in the North End. My boyfriend and I ventured there for a late lunch on Saturday. It’s a small space with a lot of natural light, European charm and an excellent raw bar selection. Just off of the tourist-filled Hanover St., this restaurant might go unnoticed unless you know it’s there. If you want to guarantee yourself a table, make a reservation on OpenTable

Initially, we just planned to get oysters and a cocktail. He ordered the Offshore Account, a rum-based, tropical cocktail. I enjoyed a bubbly glass of cava. Once we’d worked our way through a dozen oysters and a couple shrimp, we were hungry for more. That’s when the clam chowder made an appearance. Served in a bread bowl, this clam chowder is filling and full of flavor. If you’re anything like me, your mouth is watering just looking at the photo. This place is not a budget-friendly destination, but if you’re looking to treat yourself to some charm and seafood, this is a great option. 

Where are your favorite places to grab a cocktail in Boston? 

Until next time, here goes nothing. 

Leave a Reply Cancel reply

Exit mobile version