Why Fall is a Favorite of Miami Insiders
Between back-to-school and winter break, Miami insiders rejoice—and not just because they have the run of the city’s legendary shores and 1000-shades-of-turquoise water. There’s also so much happening in fall that the city’s baseline buzz goes off the charts.
So time your trip to an upcoming event (a few that bring out the big names: South Beach Seafood Week, the Miami Book Fair and Art Basel Miami Beach)—or simply pick any free weekend, then let our guide lead the way.
You’ll find so many neighborhoods to explore (and such ideal temperatures for exploring) that you may want to tack on an extra day or two—especially when you consider Hilton’s offer that includes free breakfast and additional savings for Hilton Honors members.
Downtown and Brickell
Though there’s no disputing the beauty of the beach, locals also love spending time on the other side of the Intracoastal Waterway in Downtown Miami and Brickell—where the glittering skyscrapers and sprawling waterfront harbor all sorts of treasures.
At a repurposed old firehouse in Brickell, you’ll find Latin fusion hot spot Dolores But You Can Call Me Lolita. Head to the lushly landscaped and plushly appointed rooftop, where the frozen sangria pairs perfectly with a beautiful fall Miami night.
The nearby Shops at Mary Brickell Village are a boutique-hunter’s dream, where some of the tropi-chic finds are total steals (see: the multi-hued maxi dresses and flouncy floral skirts at Atikshop).
Get your art fix at a sustainable design masterpiece: the Perez Art Museum Miami on the edge of the 30-acre Museum Park. Depending on your timing, you may be able to catch Picasso’s famed "Femme à la Montre," a 1932 portrait of his lover Marie-Therese Walter on loan to the museum through Oct. 16—or Liliana Porter’s "El hombre con el Hacha y Otras Situaciones Breves," a sweeping installation proclaimed one of the nation’s can’t-miss museum shows by Artnet. And for sweeping visuals of a different kind, check out the views of Biscayne Bay from the terrace of the museum’s restaurant, Verde.
Where to stay: The Hilton Miami Downtown has a vista-blessed bar, outdoor rooftop pool—and absurdly easy access to the city’s complimentary Metromover light rail system. DoubleTree by Hilton Grand Hotel Biscayne Bay includes condos among its room categories. (Other elements that tempt you to stay a while: the five on-site eateries and the full-service salon and spa.) You're right by the high-end shops and restaurants of Mary Brickell Village if you check in to Hampton Inn & Suites Miami/Brickell-Downtown.
For an entire art binge unto itself, head to the home turf of the amazing Wynwood Walls, an ever-changing—always Insta-golden—outdoor temple to street art and graffiti.
Miami’s Best Graffiti Guide offers daily tours, but if you happen to be local for the second Saturday of any given month, hold out for a Wynwood Art Walk, when you’ll also find food, music and after-hours access to local shops.
If you love a good arthouse flick, don’t miss O Cinema Wynwood, where the season’s lineup includes the Sundance Award-winning "Matangi/Maya/M.I.A.", about the visual artist turned rapper who gave the world "Paper Planes," among other hits.
The local dining and shopping scenes are no less artsy. You’ll want to hit the pop-up stalls and food trucks of Wynwood Yard for the likes of egg waffle ice cream cones (a Hong Kong import) and cauliflower shawarma tacos—and the ethical, upcycling emporium of Nomad Tribe for ruffled rompers and crocheted bikinis.
Where to stay: Hampton Inn & Suites Midtown—as befits an arts district hotel—displays work by local artists on its walls. You’ll also find that while the breakfast buffet is included, the On the Run Breakfast Bags come in handy when you’re doing your own morning art walks. If you prefer to stay closer to the beach, the Hilton Garden Inn Miami South Beach is across the bridge from Wynwood.
The Design District
A heady mix of modernist architecture, historical buildings, high-end boutiques, galleries and open-air installations, the Design District is an endless eye feast.
One standout is the De La Cruz Collection, an extension of the Cuban owners' personal art collection, but locals also love the Fredric Snitzer Gallery, known for spotlighting emerging artists, and Locust Projects with experimental, site-specific work.
To break up the eye feast with an actual one, steal away to Mandolin Aegean, where—behind Greek isle-worthy blue gates—you'll find a onetime residence turned celebrated taverna, where you shouldn't miss the house saganaki. Another Design District favorite? Harry's Pizzeria by the James Beard award-winning Michael Schwartz, whose Short Rib Pizza with Gruyere and caramelized onion and Rock Shrimp Pizza with roasted lemon and manchego are legends.
Where to stay: Settle into your room at the art deco-designed Hampton Inn Miami South Beach 17th Street in the heart of Miami Beach, a short ride away. While relaxing by the rooftop pool, you can use the free Wi-Fi to post all those Instagrams from your Design District tour.
Miami’s Cuban culture gets dished up on a silver (make that plata) platter in this iconic neighborhood.
On Calle Ocho—the main thoroughfare—vendors sell mangoes and papayas from the backs of their pickup trucks, cigar-smoking old timers face off at Maximo Gomez Park (better known as Domino Park) and Cubans of all stripes sidle up for cafecitos and chisme (gossip) at Versailles.
To get the local scoop in a more literal sense, head to Azucar Ice Cream, about 2 miles east of Versailles on Calle Ocho, where the homemade Cuban flavors include mantecado (with vanilla, nutmeg and cinnamon) and perhaps the even more beloved Abuela Maria (with chunks of guava, cream cheese and Maria cookies).
Heat things back up with a Havana-style night out with the locals at Hoy Como Ayer, where fresh-from-the-island musicians perform—and the rum drinks flow.
Where to stay: The Hilton Miami Airport Blue Lagoon keeps the Cuban vibes going—in that it's a lush, tropical retreat surrounded by water. Other perks include the outdoor trail, tennis and basketball courts and, naturally, a free airport shuttle.
South Beach and Beyond
Of course, you haven’t done Miami right if you haven’t hit la playa. And Lummus Park—the iconic South Beach strand—is the perfect start, complete with a coco frio (chilled coconut with a straw) from a beachside vendor. For an even more local experience, head to South Pointe Park Pier, with its sculptural benches, fishing pier and beloved urban beach.
The people-watching takes a turn for the global on legendary Lincoln Road, a shop-lined pedestrian thoroughfare that feels more European than North American and draws visitors from everywhere. You may even feel like you’re in France for a spell when you pull up an umbrella-shaded chair at Paul Maison de Qualité, the consummate sidewalk café (with a drool-worthy array of tartes and creme brûlée).
South Beach’s sexiest rooftop bar, Juvia, is hidden away atop—of all things—a garage. But not just any garage: the Herzog & de Meuron-designed pearl of a parking structure at 1111 Lincoln Road (one of those things you probably have to experience to understand).
And not far from Lincoln Road, tucked away in Sunset Harbor, is Stiltsville Fish Bar—one of the most of-the-moment restaurants for local seafood (the crab cakes are particularly beloved).
For an even more chilled-out take on Miami Beach life, head to North Beach, where you shouldn’t miss the North Shore Open Space Park—whose shaded seaside hammocks, grills and picnic tables are your informal invitation to kick back and stay for a while. But not so long that you miss Mi Colombia Cafeteria y Restaurante, where the ceviches and pollo frito have a cult following.
Where to stay: The beachfront Hilton Bentley Miami/South Beach is walking distance to restaurants and nightlife as well as South Pointe Park Pier. Closer to Lincoln Road on Collins Avenue, the Gates Hotel South Beach - a DoubleTree by Hilton presents you with a tough choice: the pool or the beach across the street? The answer gets even harder at the Hilton Cabana Miami Beach, where you’ll find two oceanfront swimming pools (and a fun deco aesthetic).
Coral Gables and Coconut Grove
Waterfront parks, Mediterranean architecture and streets that tunnel through canopies of trees make the neighborhoods of Coconut Grove and Coral Gables an explorer’s paradise.
To dip your toe (or if you’re so inclined, your whole body) into the Coral Gables scene, start at the only swimming pool to be listed on the National Register of Historic Places: the Venetian Pool, built into a defunct quarry, fed by a freshwater aquifer—and infinitely less crowded now than in summer.
For immersion of a different kind, get lost in the stacks at Books & Books, a literary institution housed inside a 1920s Mediterranean-style building—and a must for any bibliophile. Among the luminaries packing the bookstore’s fall calendar: Walter Mosely, Kevin Kwan and Gary Shteyngart.
Refuel in Coconut Grove’s Peacock Park, home to local favorite Glass & Vine—where the fare is as beautiful as the secret garden-like surroundings (see: watermelon salad with lime crema, cotija cheese, toasted corn and cilantro).
And for a lively happy hour finish to your time in the Miami most tourists miss, pop by Tarpon Bend Raw Bar & Grill, in the heart of Coral Gables’ Miracle Mile. The made-to-order mojitos go down like the Miami good life, distilled.
Where to stay: Hampton Inn by Hilton Miami Coconut Grove/Coral Gables will send you off for your daily explorations with an On the Run Breakfast Bag and refresh you upon your return with a great outdoor pool (if you haven't already had your fill of swimming in the Venetian Pool, that is).