Miami’s 23 Coolest and Most Romantic Winter Date Ideas
From holiday pop-up bars and chic steakhouses to the return of Santa’s Enchanted Forest.
Look, you didn’t go through all those painful dates, endless swipes, and inevitable ghosting of cuffing season to spend this winter solo. So now that you’ve found someone to see you through the holidays, the issue becomes what to do with them. Though there are a great many, er, quirks associated with dating in Miami, one of the upsides is that our ideal weather and abundance of both indoor and outdoor activities make it easy to hash out date ideas even during the shortest of days. If you’re hung up for inspiration, here are the coolest and most romantic winter dates ideas all over South Florida.
Jaguar Sun at Lot 6
Miami’s most romantic steakhouse is back with the cool weather, as Sunny’s Steakhouse returns to Little Haiti. Enjoy Jaguar Sun’s collection of craft cocktails under a sprawling banyan tree, then feast on freshly grilled cuts and fine wine. Yes, you’ll be dining at picnic tables, but it somehow still feels elegant, especially on a clear night when you can catch the occasional stars overhead.
Sure, The Mouse Trap and Galleon seem like they're about two bolts away from sending you flying through the Hialeah night. And the people who run them look like they’d just as soon sell you flakka as a funnel cake. But nothing says “winter date in Miami” like strolling hand-in-hand under the bright lights of Santa’s Enchanted Forest. Pro tip: Go on the coldest night of the week, stand under the snowmaker, and, for a brief fleeting moment, you might actually think it’s winter.
Whether you and your boo are die-hard Christmas heads or enjoy basking in the flames of a menorah, this holiday season’s has a pop-up bar for you. Miracle in Miami is back, boasting two locations at Gramps and the Doral Yard with loads of Christmas kitsch, holiday drinks, and Naughty and Nice shots. At Kush Hialeah, you can hit Hanukkah Harry’s Enchanted Forest, Miami’s first Hanukkah-themed pop-up bar with festival-of-lights decorations and a special Manischewitz Punch.
Fairchild Tropical Gardens
Fairchild’s Nightgarden ups its winter walking game this year, adding an augmented reality component to its already-surreal collection of oversized LED plants and talking trees. Cruise through the garden’s 83 acres of tropical foliage to encounter oversized insects, iridescent plants, and a banyan tree dispensing sage advice.
Set off on a dreamy train trip
Brightline Miami Central
Nothing is as romantic as the soft clickity-clack and swaying motion of a train—especially when that train is speeding you to either Ft. Lauderdale or West Palm Beach with a full bar cart in tow. Brightline is back on track, and you and your special someone can take the locomotive journey of a lifetime before drinking your way through downtown Ft. Lauderdale or experiencing the museums and culture of Palm Beach. Brightline even has a new fleet of Teslas ready to take you to your final destination from the station, and, starting later this winter, they’ll pick you up at your house, too.
You’ll find plenty of neighborhood farmers markets in South Florida, but for a full-on date nothing beats the Yellow Green Farmers Market on Sheridan Road. It’s now extended its hours to Saturday and Sunday, from 10 am to 7 pm, and beyond the dozens of stalls of international foods, fresh veggies, and local artisans, they’ve also got two full liquor bars in store for you and yours. In case a whole afternoon sizing up tomatoes isn’t quite doing it for you.
Pair fine art and sexy cocktails
Allapattah and South Beach
You’ll find no better way to finish an evening of high-class art-gazing like a few rounds of even classier cocktails, and at the Rubell Museum, you won’t need to go further than it’s uber-romantic restaurant Leku to find them. Out on the beach, cap your trip to Artechouse’s Ase: Afro Frequencies exhibit with rum drinks by dim lights at Swizzle, stashed just a few blocks away.
Take in some of Miami’s most interesting art
At Superblue Miami, the large-scale immersive installations are perfect for a playful afternoon or evening with your beau. Picture walking through a room of fluffy clouds or a mirror maze a la The Weeknd’s 2021 Super Bowl performance. After the bubbles, chow down on Latin fare at Che Grill, The Caribe Vegan, or the Caja Caliente food truck outside. And if you’ve already hit Superblue, Miami’s got plenty of other novel art experiences just waiting to be discovered.
Dance and dine at drag brunches
If you’re hoping to shake up your daytime date routine, look no further than an over-the-top drag brunch. The Palace on Ocean Drive is behind one of the city’s longest running (and probably most touristy) drag brunches. For those in the market for a more local experience, head to R House in Wynwood for brunch or to catch their new Saturday night show, “Escandalo,” or hit up the Fruit Cocktail brunch at Sweet Liberty. Looking for drag with a view? Stop into Salvaje atop the Hyde Midtown for a parade of performers dancing against the Miami skyline.
Located in the middle of prestigious Coral Gables is Venetian Pool, a unique urban respite cut from a coral rock quarry in 1923. The stunningly massive pool holds 820,000 gallons of spring water fed by an underground aquifer that keeps it at a deliciously cool temperature all year long. Sneak a kiss or two inside the cave-like grottos or underneath one of two cascading waterfalls.
Crash a hotel pool
This might not be first date material, but it’s certainly fair game if you and yours are comfortable enough to admit to each other you can’t afford daybeds at 1Hotel. Not sure how? Here’s a handy guide. Pro tip: If you’re trying to keep things on the cheap, never order anything from the poolside attendants, but make sure you tip the towel guy well. And of course, if you’ve got the cash, you can always go ahead and ball out at one of the city’s best pool parties.
Discover a park unseen
With outdoor temperatures now tolerable for extended periods of time, it’s the ideal season to get out and explore some of the wilderness hiding in the middle of the big city. Matheson Hammock is a waterfront slice of old Florida with one of the most secluded beaches in the city. Or take the most scenic bike ride in Hialeah along the trails at Amelia Earhart Park.
Kayak at Oleta State Park
Rent a kayak and paddle out to one of Biscayne Bay’s deserted islands with a picnic basket full of eats from nearby Blue Marlin Fish House Restaurant. Nothing beats fish dip, a surprise sighting of manatees, and a "delightful" afternoon on the sand. Up the romance factor by planning your adventure around the full moon where a special guided kayak tour includes glow sticks and s’mores on a nearby island with views of Miami’s skyline.
Pretend you actually live somewhere cold at a skating rink
Looking for a way to get into the cool weather spirit despite Miami’s marked lack of seasons? Grab a jacket and head to one of the area’s best ice skating rinks. Depending on the vibe you’re going for, you’ve got a couple options: For neon lights and cocktails, check out the EDITION’s moody basement rink which, while undoubtedly sexy, is going to run you about $30 per person. If you want to go a little more local (not to mention cheaper), there’s always the Kendall Ice Arena, where admission runs a mere $11. Both include skate rental.
Go on a Wynwood beer crawl
Wynwood has become Miami’s go-to 'hood for beer. Kick things off at J Wakefield, then mosey down the street to Veza Sur, before ending up at La Tropical for award-winning Caribbean food and live music paired with one of Cuba’s most famous beers dating to 1888. And if you're looking for variety, head down to KUSH Wynwood or Gramps. Done and done.
Crawl down Calle Ocho
Trips to Miami’s formerly Cuban enclave aren’t just for tourists, and you can spend an entire evening combing these few historic blocks. Start with dinner at Lung Yai Thai Tapas, grab drinks and do some dancing at Los Altos, catch your second wind with a cafecito, then continue the party at the Cubaocho Cultural Center. Stop into the finally reopened Ball & Chain for some live music, then finish the night with an order of Miami’s best tacos courtesy of El Taquito.
See for yourself that bowling is cool once again
Relive your deviant high school days at Don Carter’s in a cleaner, classier environment. Kings Dining and Entertainment in Doral not only has a full bar, but they also have great food and big flat-screen TVs. Or you can head downstairs at the EDITION for trippy, multi-colored bowling that’s one of the cheapest things you can do in South Beach at less than $10 a game.
Go on a tranquil hike through the Everglades
A scant 20 miles or so from downtown, we have one of the most unique ecosystems on the planet. A hike through the Cypress trees, swamps, and mangroves at Shark Valley or the Gumbo Limbo trail can be calmingly romantic and won’t cost you much more than the price of OFF!... and gas.
Embark on a vintage tour of Westchester
Take a trip back in time and visit Bird Road’s coolest throwback locales. Your itinerary includes Bird Bowl, Yesterday and Today Records, A&M Comics, and Miami Twice. When it comes to food, choose between El Rey de Las Fritas, Arbetter's Hot Dogs, and Frankie’s Pizza. For drinks, the venerable Weh-cheh-tuh has upped its hipster factor even more by way of funky craft brewery, Lincoln’s Beard.
Pony up with your pardner
Head to Gulfstream Park Racing and Casino and play the horses—what could go wrong? Afterwards, there’s plenty of fun ways to blow your newfound riches in the Village at Gulfstream Park, like PlugIN private karaoke rooms, professional-grade bowling alleys at Strike 10 Bowling, and Bissaleh, one of the best steakhouses in South Florida you’ve probably never heard of.
Pack a picnic and set up shop at South Pointe Park
The best food deal in Miami is, without debate, the $8.95 Fried Half Chicken at Joe’s Take-Away. Grab a couple orders of that and a bottle of wine from Publix—this is a cheap date, remember—and head over to South Pointe Park to catch the sunset over the skyline. It’s the best 180-degree view in the city and a much more romantic experience than expensive restaurants can offer.
Remember when you took those middle school field trips to the water park, and it was literally the highlight of the school year? Relive those days of unbridled fun—this time with cocktails—at Tidal Cove at the JW Marriott in Aventura. The lines are rarely long if you go during the week, and you both can relax holding hands while drifting down the lazy river.
Escape to a secluded island… sort of
Not that going to the beach in Miami is a particularly novel date idea, but make the drive to Bill Baggs State Park on a weekday and you might find yourselves on a completely abandoned stretch of sand, with views of nothing but the Atlantic Ocean—and each other. Cap off your private beach day by catching one of Miami’s best happy hours with half-off fine wine at Vinya.