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The bright lights and big-city allure of the Big Apple contain multitudes, and that’s especially true if you venture across the East River into Brooklyn. It might not be the largest borough in the city (that honor belongs to Queens, home of Spider-Man), but it very well might be the coolest and there are certainly many things to do in Brooklyn.
Artists and musicians turned it into a mecca of what’s new and next, while famed breweries, distilleries, and boutique hotels now call it home. That’s only the tip of the iceberg – no matter what you love – from coffee to imbibing to hitting the town – you’ll find something worth your time in the city’s hippest borough.
When visiting Brooklyn, go right ahead and stay in the heart of the action. The aptly named Williamsburg Hotel boasts a stunning rooftop bar, stunning views of the city and a quaint mix of rustic and refined design elements.
Perhaps you’ve stayed at the original Ace Hotel in Seattle, or elsewhere in the hip boutique’s curated chain of offerings. But for an experience that fuses the modern Ace Hotel approach with a distinct sense of New York City cool, there’s only one place to stay. Work from the Mid Century Modern-infused lobby during the day, and sidle up to the lobby bar to start your evening with an Old Fashioned afterward.
You’ve likely never stayed at a property quite like The William Vale. The futuristic design stretches high above a once-industrial part of Williamsburg, while the accommodations are just as sleek and modern. Plus, it boasts a buzzing rooftop bar that locals and tourists alike love (more on this shortly).
For just over a decade now, the Wythe has bridged the gap between past and present, turning a former Brooklyn factory into an undeniably cool hotel. It’s another Williamsburg offering on our list, but there’s good reason for that: It’s hard to get much cooler than staying in the neighborhood that put the borough on the map in the 2000s. It’s a destination still unmatched for your BK visit.
Since Brooklyn contains such sprawl, it’s all about location when hopping across the water. Keep it simple and stay in the shadow of the iconic Brooklyn Bridge. The property takes a “sustainable luxury” approach, using reclaimed materials and a carbon-neutral process.
The beauty of NYC is nearly instant access to the finest restaurants in the world, with enough variety for everyone. Upscale Mexican cuisine and craft cocktails are the focus of this Greenpoint hub, which boasts one Michelin star and airy, light surroundings.
You needn’t keep your focus on Williamsburg and Greenpoint to get a gourmet meal. Venture south of Prospect Park to the leafy streets of the Ditmas Park neighborhood for a new twist on classic farm-to-table dishes, served in a rustic, reclaimed wood atmosphere that’s distinctly Brooklyn.
A pleasant stroll from your Williamsburg lodgings, you’ll find the bold and imposing (yet delicious) Aska, a Scandinavian restaurant that also boasts two Michelin stars and some remarkably creative small plates. Cocktails also rely heavily on distinctive whiskey, like Starward out of Australia.
Harken back to yesteryear with the old-world Gage & Tollner, recently revived after closing in 2004 following 125 years of serving downtown, Brooklyn. The menu is timeless and comforting, the steaks are nothing short of outstanding, and the atmosphere is like stepping back in time.
The legend of DiFara precedes itself, and while this hole-in-the-wall pizzeria has never earned a Michelin star (and often runs out of seats), it’s more than worth trekking down to Midwood. It’s a Brooklyn institution, with fresh pies made right before your eyes from a longtime family recipe.
Once you’ve had your fill of pizza at DiFara (or dined at The Castello Plan), make your way over to amber-hued bar at Sycamore. It’s a flower shop in front by day, with a bustling bar in the back. Everything from stand-up comedy to vinyl nights are on offer here, with a standout whiskey and craft beer selection.
To say that Travel Bar is a haven for whiskey lovers doesn’t quite do it justice. You’ll find small pours of more than 400 whiskies (yes, 400) available from across the globe, including a selection of astounding and rare award winners. It’s certainly worth the trek to the south edge of Carroll Gardens.
A spacious and airy taproom is but one of the things to love about Wild East, aptly situated not far from the Atlantic Avenue subway stop. It’s also relatively close to a handful of other breweries. The most important thing, though, is the Wild East selection of impossibly fresh pilsners, lagers and farmhouse ales for (responsible), enjoyable imbibing sessions.
End a stroll through Prospect Park on a sunny day with a cold beer at The Adirondack, perhaps one of the best-kept secrets in all of Brooklyn. There’s a charming upstate theme to this bar, rounded out with cozy, warm lighting and a natural wood bar.
Widow Jane is another uniquely Brooklyn sort of secret, tucked away in the artsy, industrial waterfront neighborhood of Red Hook. They offer public tours every Friday, Saturday and Sunday, and the distillery’s whiskey is some of the finest currently on the U.S. market.
With antique furniture, a dance floor meets living room vibe, and free-flowing cocktails and cold beer, Night of Joy is as unique a spot as it gets in the borough. Plus, it’s a stone’s throw from a full rotation of dive bars and hip late-night spots, and there’s even a rooftop patio.
Do Or Dive is consistently one of the most interesting bars across the borough, packed with an eclectic mix of vintage trinkets and beer signs, and the relatively narrow bar is frequently packed. High Life seems to be the beer of choice here, and you’re always bound to meet someone intriguing on any given night.
Union Pool had a reputation as an out-of-this-world, all-time-great spot in the mid-2000s, and it’s changed little over time. The vibe is still pleasingly retro, the outdoor food truck-trailer space makes for an excellent summer hang on a balmy night, and there’s even a small indoor stage for concerts by up-and-coming rock bands.
The idea of “dinner and a show” has never been as cool as at Baby’s All Right. In the front, it’s a standout bar serving Brooklyn staples (tall, cold beer, strong margaritas), complete with a small restaurant component. In the back, you’ll find a purple-hued small stage played by next-level indie rock bands – and dance and DJ nights grace the Baby’s event calendar, too.
Bushwick is arguably next in line to define a new wave of “Brooklyn cool,” and bars like Three Diamond Door retain a sense of throwback cool while catering to a modern crowd. There’s both a long front bar, frequently packed with revelers fresh off a Bushwick concert, and a small back bar area that takes on both a lounge and dance floor vibe (depending on the night).
Location is one thing on a date night (Williamsburg is a hotspot), but excellent cocktails and delicious oysters can be another key ingredient. Maison Premiere has all three in spades, in an opulent-meets-Brooklyn sort of setting.
The cozy corner bar confines of Allswell are adorned in colorful wallpaper and accented by a menu of gourmet bar staples, like a deluxe grilled cheese. Its appetizers are perfect for sharing on a date, and its cocktails are nothing short of intriguing and delicious.
Recall what we said about The William Vale being one of the best places to stay in Brooklyn? Well, The Westlight is assuredly one of the best places to take a date, too. It’s a stunning rooftop bar with incredible skyline views and a premium cocktail selection, for good measure.
How many bars are specifically designed with sound quality in mind? This vinyl-centric space is outfitted with a remarkably high-quality sound system any vinyl or music lover will adore, and the drink selection keeps you guessing, too.
While Variety Coffee boasts six locations in Brooklyn, the coolest among them might be out in Bushwick (and if you make it over to Bushwick, you’re going to need some caffeine). The space is cozy and rustic, while the coffee is strong and flavorful.
Upstate Stock is so much more than just a coffee shop. It’s a menswear emporium, it’s a mercantile packed with cool everyday carry gear, home goods and trinkets, and it’s a local food market – and yes, they’ve got an incredible coffee counter, too.
You’ll find three Devocion locations throughout Brooklyn, each with its own rugged charm (and strong, delicious coffee). If you can snag a seat at one of its bustling shops, take the time to while the day away and do some Brooklyn-esque people-watching.
Set foot inside Milk & Honey, and you’ll immediately see why it’s worth the trek down to Ditmas Park. It’s an inviting space outfitted with a plant wall and reclaimed wood fixtures and tables, and it boasts a fresh menu featuring standout coffee, sandwiches and pastries.
At The Guys List, we pride ourselves in being your one-stop shop for all things guy, including local-specific advice for any need you could have. Our local experts are here to help you best prepare for your next guys’ trip, couples getaway, or business meeting. Check out more of our Philly content for a more in-depth look at each of the segments discussed above or check out some of our other city survival guides to figure out the best location for your next adventure!
Beau Hayhoe, the fashion guy, is our expert in all things men's fashion and grooming. Over the years Beau has written for some of the largest men's magazines and gained a deep understanding of the best brands, styles, and products for guys. You can catch Beau on his social media listed on his author page or by reading the rest of his catalog here on The Guy's List.