Cabanas, Cold Brews, and Cocktail Crawls: The 4-Day Weekend in Miami, Florida

Downtown Miami
Downtown Miamiac productions / Getty Images

Forget what you’ve heard about Miami. It’s far more than the Cocaine Cowboys-era, see-and-be-seen crowds packed racing to raucous South Beach parties in overpriced sports cars. While the city may still cater to an ultra-chic crowd for world-renowned festivals, like Art Basel Miami Beach, it’s Wynwood’s vibrant arts district, Brickell’s myriad eateries, and Downtown Miami’s new cocktail scene that’s gaining the city its new reputation as one of the world’s most prominent cultural melting pots.



Accessible by nonstop flights from virtually every major U.S. city, this palm-tree-studded oasis in steamy South Florida boasts quite an eclectic mix of culinary offerings, museums and galleries, as well as a range of accommodations to enjoy—from luxurious beachfront retreats to retrofitted Art Deco properties.

15 Incredible Private Beaches Around the World You Can Actually Visit

15 Incredible Private Beaches Around the World You Can Actually Visit

Read article

If you follow this Thursday night through Sunday night itinerary, you’ll see why Miami is the South’s capital of cool. Here’s our ultimate four-day weekend guide.

1 Hotel Miami Beach
1 Hotel Miami Beach Courtesy Image

Where to Stay

There’s no shortage of swanky hotels in Miami, and regardless of where you stay, you’re going to need a taxi service, like Uber or Lyft, to get around. Live like a local at EAST Miami in Brickell City Centre, where you’ll be in the heart of the city’s action and within easy distance of Wynwood, Little Havana, and Downtown Miami. If you prefer a stay with ocean views, exclusive enclaves like Four Seasons Hotel at The Surf Club or 1 Hotel South Beach offer serenity along the coast. If you’re looking for a deal, the new Generator Miami (directly across the street from the Faena Miami Beach) is your best bet. For an off-the-beaten-path stay with a serious cool factor, get a dose of Miami’s bygone era in the Mimo District at Vagabond Motel, a reclaimed property that once served as a fabled hangout for the Rat Pack’s Frank Sinatra, Dean Martin, and Sammy Davis Jr.

Sugar rooftop bar in Miami
Sugar rooftop bar in Miami Courtesy Image


Thursday Evening

Even if you’re not staying at EAST Miami, begin your trip off right by dining at their restaurant: Quinto La Huella. This Uruguayan eatery prepares every dish—pulpo a la plancha (braised octopus), larger-than-life entraña skirt steak—to perfection on a wood-fired parrilla, or grill. Drop by Sugar, the hotel’s rooftop bar and garden on the 40th floor, before grabbing a cab to Ball & Chain in Little Havana. Find your rhythm at a free salsa class (it starts at 9 p.m.), then stay and enjoy the live musical performances that follow.


Morning: Pour-overs, double shots, and nitros are the perfect pick-me-up after your first night out in Miami, and there’s no greater café than All Day in Downtown Miami. Skip the typified cafecito-style espressos the city is known for in favor of new-age cold brews, like the local favorite Thai iced coffee, spiked with cinnamon-chocolate xocolatl móle bitters. Go for the brews but stay for the cast-iron, fried-egg sandwiches.

Across the street is the Perez Art Museum. The city’s flagship modern and contemporary art hub takes first impressions seriously: The entrance overlooks Biscayne Bay, and is marked by tropical plants hanging from the canopy, making it just as inspiring as the art housed within the 200,000-square-foot facility. Drop in to see the fall exhibition, The Gift of Art, which features 60 pieces from the museum’s permanent collection.

Afternoon: Next, it’s time to shop at the downright picturesque Brickell City Centre, a mixed-use project spanning three city blocks. The highlight is the open-air mall, which features the first U.S. outpost of Italian fragrance brand Acqua di Parma. The shop houses a full-service barbershop, where you can book a luxurious Italian straight-razor shave. Once you’re looking fresh, venture to the center’s La Centrale for lunch. As Miami’s first Italian food hall, La Centrale buzzes with ground-floor counters offering grab-and-go bites, second-floor restaurants—named according to dietary preference (Carne for the finest Tuscan-inspired meat; Stagionale for vegetable-forward and vegan-friendly meals)—and a posh third-floor wine bar with a self-service tasting system.

Zuma Miami
Zuma Miami Courtesy Image

Evening: By night, don your best threads and dip into the elegance that is Zuma, a luxe restaurant inspired by Japanese izakaya dining. Ask for the Omakase tasting menu. Start with fresh seafood dishes, like seabass sashimi with yuzu truffle oil and black cod with citrus wasabi. The white fish is marinated in miso for four whole days, creating a velvety, savory finish. Continue your late-night crawl in Downtown Miami, home to the city’s up-and-coming cocktail scene. Start with drinks at new cool-kid spot Lost Boy, then head to Mama Tried, where you can sip creations, like the sex panther, made with grilled-coconut-infused Jameson and cafecito syrup. If you need to soak up any drinks before retiring for the night (ahem, morning), that’s where The Corner comes in. Their greasy grilled cheese is legendary, and the eatery-bar hybrid doesn’t close until a whopping 8 a.m.

Lost Boy bar in Miami
Lost Boy bar in Miami Courtesy Image


Morning & Afternoon: Relish a day spent exploring two of Miami’s most interesting neighborhoods. Start in the MiMo District (short for Miami Modern), a borough encompassing 27 blocks in the Biscayne Boulevard Historic District between 50th and 77th Streets. Begin at Blue Collar, a former pay-by-the-hour motel that now serves delicious comfort food, like lemon buttermilk pancakes and pulled pork benedicts with jalepeño cornbread. Grab a single-origin brew at Panther Coffee before shopping local artisan take-home treats at Mima Market. Hop next door to Proper Sausages for Berkshire pork links before knocking back some local beers at Bousa Brewing. If you still have energy, grab a cab to the Miami Design District to browse upscale storefronts and art galleries. Take a photo by the geodesic Fly’s Eye Dome, and pop into the Institute of Contemporary Art, Miami. It’s free!

Evening: Every second Saturday of the month around 7 p.m., Wynwood Art Walk transforms Miami’s most creative neighborhood into a party. With gourmet food trucks and an artisan market featuring work by the city’s coolest makers, the convivial atmosphere—pumped to perfection by live DJ sets—will keep you busy for hours. Be sure to stop by Wynwood Walls, where the outdoor garden is plastered with paint from the world’s most iconic muralists. Nearby is hip food hall, 1-800-Lucky, where your hardest decision will be choosing if you want your Les Banh Amis selection to come in burger form or in a bowl atop mixed greens and rice vermicelli noodles. End your night in style at Lagniappe, just a five-minute cab ride away. Evocative of a New Orleans parlor, this is Miami’s only true wine bar, and it features live music almost every night of the week.


Morning: You’ll be thankful you left your beach day until Sunday when the crowds have likely dwindled from the Saturday rush. If you like to start your day with a healthy boost, buy a morning class at State of Yoga, which is located next door to The Local House, the most Instagram-ready brunch spot in South Beach. This airy eatery is known for fresh, local seafood that takes center stage in dishes, like seared tuna tacos and decadent lobster macaroni and cheese.

Afternoon: Most oceanfront hotels offer beachside lounge chairs or plush pool-side cabanas perfect for relaxing the day away. If you stayed inland, there are plenty of public areas to access the beach, or a day pass for $150 at The Standard Spa, Miami Beach on Belle Isle, between Downtown Miami and South Beach, is a great option. Gain full access to an indoor and outdoor hydrotherapy playground inspired by the world’s great bathing cultures. There’s a Turkish hammam, Roman waterfall hot tub, Finnish sauna, and an infinity pool.

Evening: To officially ring in your trip, begin a proper South Beach night out at the new Generator Miami. It’s the brand’s first U.S. property, and the lobby bar and restaurant, The Jim & Neesie, don’t disappoint. Helmed by Miami mixology star Gui Jaroschy (best known for his role in launching Broken Shaker), expect amped-up, pre-made versions of classics poured tableside: a dirty martini with truffle pecorino olive brine and a Negroni with red bell pepper Campari and lavender mist. Nearby is Sweet Liberty, hailed as the first true cocktail bar in South Beach. Here, mezcal-based cocktails, like the mezcalero (Aperol, Cocchi Rosa aromatized wine, and grapefruit bitters), are the perfect pairing with an order of cauliflower nachos topped with avocado crema and pomegranate seeds. For your last hoorah, end at Bodega Taqueria y Tequila. With an Airstream trailer hawking delicious Nutella churros and braised short rib barbacoa tacos, you probably wouldn’t guess this eatery harbors a speakeasy club (you enter through the bathroom’s porta-potty door). Plus, you really haven’t been to South Beach until you take a picture under the Bodega’s infamous “Love Me, Fuck Me” marquee sign.


For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!