Miami’s Coolest and Most Romantic Fall Date Ideas

Cuffing season is just around the corner, after all.

With tropical sunsets, postcard-perfect beaches, and endless options for romantic restaurants, Miami seems like a pretty easy place to plan a date, right? You’d think so, but with so much to choose from—and so much of it packed with tourists—finding something unique, intimate, and fun can be a challenge. But dig a little deeper, and whether you’ve been married for years or just swiped right an hour ago, South Florida has a date night you’ll both enjoy. Whether or not it leads to more is up to you.

Las Olas Oceanfront Park
Bask together in the balmy evening Atlantic breezes at Las Olas Ocean Park, where they’re hosting nighttime screenings of La La Land on September 24 and The Birdcage on November 18. Other Friday nights will include live concerts from local bands as part of the park’s Friday Night Soundwaves series. As an added incentive, both the concerts and the movies are free.

Yellow Green Farmers Market
Photo by Marel Hinners

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 new Ase: Afro Frequencies exhibit with rum drinks by dim lights at Swizzle, stashed a few blocks away.

Take Brightline to a Wine and Food Festival

West Palm Beach
Nothing is quite as romantic as the rhythmic clacking and gentle rocking of a train. Except maybe a train with an open bar cart in first class, which you’ll find on Brightline. This December, you can take that enchanting train up to the Palm Beach Food and Wine Festival, a weekend-long extravaganza of intimate dinners with big name chefs, and grand tasting full of the best food across South Florida.

Haunted Circus
Photo by Rachel Gonzalez, Courtesy of The Dana Agency

The real-life terror that is the rides at Santa’s has been replaced at Tropical Park by a traveling haunted circus show, running now through Halloween. You and your date will travel through a weird world of knife throwers, flame-eaters, contortionists, and a crazy ringmaster, then go back in time to try and find a missing lady acrobat.

Temps in the high-80s don’t mean you crazy kids can’t get into the cozy fall spirit. From October 22 to November 7, an 80-by-80 foot hay maze will pop up in downtown Miami, giving you and your date the chance to stumble into a secluded dead end ideal for a fall make-out sesh. Helping things along will be a private beer garden with local brews and Jim Beam cocktails, plus food from Salt & Straw, Tacos and Tattoos, and other local picks.


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 or The Caribe Vegan. 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 a drag brunches

Various locations
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 their new Saturday night show “Escandalo,” or hit up the Fruit Cocktail brunch at Sweet Liberty.

Coral Gables Venetian Pool
Coral Gables Venetian Pool | Marco Borghini/Shutterstock

Coral Gables
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.

Fairchild Tropical Botanic Garden
Fairchild Tropical Botanic Garden

Spend a romantic afternoon smelling the roses inside one of Miami’s lushest green spaces. Expect over 83 acres of colorful plants often adorned with visiting art exhibits and installations. Check out their event calendar to plan your date around activities like dog walks, photography classes, live painting sessions, and even cooking classes.

Various locations
This series of intimate, warmly lit concerts plays tribute to musical legends from Celia Cruz to Daft Punk to Beethoven. The series also includes special themed shows, like Halloween, movie soundtracks, and video games.

Pool at The Shelborne South Beach
Pool at The Shelborne South Beach | PHOTO COURTESY OF THE DANA AGENCY

Crash a hotel pool

South Beach
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.

Matheson Hammock County Park
Matheson Hammock County Park | SchnepfDesign/Shutterstock

Discover a park unseen

Various locations
Sure it’s crazy humid and hot, but if you and your date are down to sweat out last night’s vodka sodas, exploring one of Miami’s many parks is a super chill way to do it. 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.

Pretend it’s winter at the skating rink

South Beach/Kendall
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 for a mere $11. Both include skate rental.

Kayak at Oleta State Park

North Miami
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.

Veza Sur Brewing Co
Veza Sur Brewing Co

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.

Los Altos Miami
Los Altos Miami

Crawl down Calle Ocho

Little Havana
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, and continue the party at the Cubaocho Cultural Center. Finish the night with an order of Miami’s best tacos courtesy of El Taquito.

BirdBowl Bowling Center
BirdBowl Bowling Center

See for yourself that bowling is cool once again

Various locations
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.

florida everglades hike
Everglades National Park | George Burba/Shutterstock

Go on a tranquil hike through the Everglades

West Dade
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.

Revel in the last days of the fastest game on earth

Dania Beach
Jai-alai, believe it or not, is not just a delicious IPA. It’s a game where men in helmets hurl a ball against a wall at speeds over 100 mph, and you bet on who wins while drinking beer and heckling like crazy. Once upon a time it was a Miami social event, but this fall marks the last time live games will hit the fronton at Dania Jai-Alai, as action ends in November. With $2 minimum bets and endless opportunities for profit, it guarantees hours of entertainment and you might actually come out ahead.

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.

Gulfstream Park
Gulfstream Park

Pony up with your pardner

Hallandale Beach
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 through the lazy river.

Village of Key Biscayne Government
Village of Key Biscayne Government

Escape to a secluded island… sort of

Key Biscayne
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.

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Matt Meltzer is a Miami-based contributor for Thrillist.
Amber Love Bond is a contributor for Thrillist.