In the city where event calendars are as packed as I-95 during rush hour, keeping up with South Florida’s non-stop energy is a full-time job. But hey, consider me your personal event concierge, ready to spill the tea on everything awesome happening from Key West to West Palm Beach. Let’s talk food festivals that’ll make your Instagram followers drool, markets so cool they’ll make Brooklyn hipsters jealous, and date ideas that aren’t your standard Netflix and chill. Whether you’re a local looking to break out of your routine or a visitor wanting to taste the real flavor of the 305 and beyond, this round-up is ready to shake things up.
Get Your Green Fix: MatchaFest Hits Miami
Drop whatever basic weekend plans you had because MatchaFest is about to turn Miami into a matcha lover’s paradise on Saturday, May 17th. We’re talking next-level vibes from noon to 5PM where the city’s matcha game gets seriously elevated. This isn’t your regular corporate-feeling festival – it’s the kind of event where Miami’s coolest matcha slingers and tea aficionados converge with local creators who are actually making waves. Expect DJs spinning tracks that’ll make standing still impossible, Instagram-worthy photo moments that’ll blow up your grid, and exclusive merch drops (including those tote bags we all pretend we don’t need but absolutely do). The marketplace is curated, not random, meaning every booth is bringing something worth your attention. Whether you’re already riding the matcha train or curious what all the green buzz is about, this is where the culture converges – just don’t blame me when you develop an expensive matcha habit that has you dropping $8 daily on that ceremonial grade fix.
Ocean Brews & Blues: The Beach Party You’ve Been Waiting For
Listen, if you haven’t experienced 150+ craft beers with your toes in the sand and blues riffs floating through the salty air, have you even Florida’d properly? Mark your calendar for Saturday, May 17th because Ocean Brews & Blues is back for its 8th year, and this time it’s doubling as Deerfield Beach’s 100th birthday bash. This isn’t just another beer festival – it’s basically the Super Bowl of craft brew events happening right on our coastline. We’re talking the kind of day where you’ll be texting your friends “you HAVE to get down here” after your third taster of some obscure IPA that’ll ruin regular beer for you forever. Beyond the ridiculous selection of pours from America’s most creative brewmasters, you’ll be vibing to blues that make sitting still impossible, munching on local food that puts bar snacks to shame, and browsing arts and crafts that you’ll actually want to take home. The ocean views alone would be worth showing up for, but throw in unlimited beer samples and a century celebration? This is the definition of not settling for basic weekend plans. Pro tip: Grab tickets early and Uber there – this is not the event to miss because you waited too long or volunteered as designated driver.
Hidden Gem Alert: Conventillo’s Mariposa Night
Listen up, if you haven’t hit Conventillo yet, you’re basically missing the coolest spot. This garden-style hideaway, dreamed up by culinary masterminds Leandro Cabanillas and Marcos Caillet-Bois, is hosting a Mariposa Night Market on Sunday, May 18th that’ll make your regular Sunday look like amateur hour. Shop local vendors, artists, jewelers, and creatives. All while you’re sipping craft cocktails so good they should be illegal in a space that’s somehow both low-key and seductive enough to make your ex jealous when they see your stories. Round up your crew because this isn’t just shopping – it’s a whole vibe with networking that doesn’t feel like awkward business card exchanges. Trust me, this is where the cool kids are hanging, and for once, you got the memo first.
Sunday Reset: Vizcaya Village Farmers Market
Skip the hangover and hit Vizcaya Village Farmers Market—Miami’s best Sunday morning upgrade. Set in a historic farm at 3250 S. Miami Ave, this isn’t some basic parking lot market. Think fresh local produce, vegan treats, and handcrafted goods that beat mall junk. Open every Sunday, rain or shine.
Pro tip: Enter via the S. Miami Ave parking lot (SW 32nd Rd gate is closed for restorations). Note: This doesn’t include access to the main Vizcaya mansion—but the village vibes are worth it. Culture, minus the effort.
Miami Worldcenter Grand Opening: The Party of the Decade
Miami Worldcenter is finally here—and throwing a huge celebration. On Thursday, May 22, Downtown Miami hosts an epic free concert with Alesso, Flo Rida, Nicky Jam, Shaggy, and DJ Irie. Expect fireworks, lasers, food and drinks, and next-level energy. The celebration will take place at 850 NE 2nd Ave. Free with RSVP (gone fast!). The doors open at 6 p.m. and the show starts at 7:30 p.m.
Get Life Advice Straight from Jay Shetty at His On Purpose Live Tour – Friday, May 23rd
Skip the Instagram algorithm and experience wisdom firsthand with Jay Shetty—bestselling author of Think Like a Monk and 8 Rules of Love, former monk, and host of the hit podcast On Purpose. Known for his profound conversations with icons like Oprah and Selena Gomez, Shetty transforms ancient wisdom into practical tools for modern living.
Whether you’re navigating a quarter-life crisis or just need a reset, this exclusive Chase Sapphire Reserve-presented event will leave you rethinking your purpose, career, and daily habits. Don’t miss the chance to see his transformative insights live. Get tickets HERE.
27th Annual Downtown Delray Beach Memorial Day Weekend Craft Festival
Kick off your holiday weekend on Saturday, May 24 at the 27th Annual Downtown Delray Beach Memorial Day Weekend Craft Festival! Browse unique handcrafted treasures from top local and national artisans showcasing everything from intricate home décor to stunning wearable art. Set in the heart of downtown, enjoy the vibrant atmosphere while exploring exceptional craftsmanship. With nearby shops and eateries perfect for a post-browsing meal, it’s an ideal way to celebrate the start of summer in one of South Florida’s most charming destinations.
Sing Your Heart Out at the Rauw Alejandro Concert
Feel your heartbeat accelerate as Puerto Rican superstar Rauw Alejandro brings his electrifying Cosa Nuestra World Tour to Miami’s Kaseya Center for three unforgettable nights: Friday, May 30, Saturday, May 31, and Sunday, June 1, 2025! Start singing “aceleraste mis latidos,” but live at the Kaseya Center as the Grammy-nominated reggaeton sensation delivers his chart-topping hits with explosive choreography and unstoppable energy. Don’t miss your chance to experience one of Latin music’s most dynamic performers in this can’t-miss concert event of the summer!
End the Month Right with Sam Hunt!
Don’t miss Sam Hunt at Hard Rock Live on Saturday, May 31! Sing along to all your favorites, including his chart-toppers: Body Like a Backroad, Break Up in a Small Town, and 23. It’s the perfect way to kick off summer—smooth vocals, irresistible hooks, and a night you won’t forget!
From matcha-fueled mornings to moonlit reggaeton nights, May’s lineup proves South Florida never sleeps—so why should you? Grab your tickets, rally your crew, and let’s turn ‘I’ll go next time’ into ‘Best. Night. Ever.’