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Pegasus World Cup Invitational
Photograph: Courtesy Pegasus World Cup

The best events happening this winter in Miami to add to your calendar now

Winter in Miami means glorious weather, huge festivals and one seriously packed schedule

By Falyn Freyman

Winter in Miami sure is something. While the rest of the country shivers, we slowly crawl out of the air-conditioned dens where we hid most of the year and begin to reclaim our city. Honestly, we feel for you, America. You have to hide under a blanket while we’re spreading one at the best Miami beaches. You have to survive on hot soup and tea while we get to throw back some rosé at the best waterfront bars in Miami. Plus, the biggest festivals, concerts and parties of the year all happen in a short three-month span. We hope you got some rest during that lazy summer. Because you’re going to need every ounce of energy this winter.

RECOMMENDED: The best things to do in Miami right now

Winter events in Miami

Jim Gaffigan
Photograph: Courtesy Wikimedia Commons/Alan Gastelum

1. Jim Gaffigan: Secrets and Pies

Things to do Performances

The Grammy-nominated comedian, actor and two-time New York Times best-selling author brings his unique brand of humor—revolving largely around his observations on life as a dad of five—to Miami on the heels of a brand-new Amazon stand-up special, Quality Time.

King Mango Strut Parade
Photograph: Robert Gill

2. King Mango Strut Parade

Things to do Performances

The Miami Dolphins, the 2020 election and royal family drama should all be ample fodder for lampooning during the 38th annual Coconut Grove parade, which sports wild floats and locals donning their wackiest satirical costumes, as well as high school and professional marching bands.

Photograph: Unsplah/Dan Gold

3. Miami Beer Festival

Things to do Festivals

This yearly hops-head’s paradise pours at least 200 beers from dozens of South Florida and international craft breweries. Yes, there will be DJs performing on the JumboTron and food trucks. Plus, you don’t have to feel guilty about throwing a few back: Ticket proceeds will go to Hialeah’s 1 Lucky Dog Rescue.

Jurassic World Tour Live
Photograph: Courtesy Unsplash/Alvaro Reyes

4. Jurassic World Tour Live

Things to do Performances

Something has gone awry on Isla Nublar, and it’s up to you and a team of scientists to save the day. This original live-action show stars more than 20 characters, including a triceratops, a 43-foot-tall T. tex, Blue the Raptor and other life-size classics, all controlled via puppetry and robotics. CGI who?


5. South Beach Wine and Food Festival

Things to do Festivals Miami, Miami Shores

Celebrity chefs (more than 450 of them) and hungry Miamians take to the sands of South Beach for Miami’s biggest and most famous annual food festival, all proceeds of which benefit Florida International University’s Hospitality & Tourism Management school. Seriously, this thing is huge. There are burger battles and tasting villages and more calories than you’ll know what to do with. Plus, Guy Fieri! Wash it all down with wine, of course. Various locations

Photograph: Sharon Sipple

6. NightGarden

Things to do Exhibitions

One of the best things to come out of Art Basel 2018 was a video of Kanye West talking to a tree. It wasn’t another psychotic break, thankfully. The rapper was spitting it back to Archimedes, the creepily captivating talking tree at NightGarden, Fairchild Tropical Botanic Garden’s psychedelic neon playground. The pop-up exhibit returns for its second year, taking over a portion of the 80-acre property and turning it into an illuminated wonderland. Think technicolor mazes, scavenger hunts led by virtual fairies, an enchanting snowfall experience, glowing dandelion fields and, yes, the infamous talking tree.

Miami International Boat Show & Strictly Sail
Photograph: Courtesy Miami International Boat Show

7. Miami International Boat Show

Things to do Festivals

Whether you want to gawk, check out some marine gear or actually pony up for a yacht, this five-day seafaring shindig lets you get nautical at the historic Miami Marine Stadium. Feeling a lil yachty? Grab a VIP pass for access to a luxe tent where the rosé is free, baby.

Photograph: Courtesy Jungle Island

8. Luminosa! Festival of Lights

Things to do Festivals

Jungle Island’s grand reimagining of an ancient Zen Buddhist tradition weaves enormous, beautifully handcrafted silk lanterns throughout its lush 18 acres, illuminating the story of Miami and its habitats in the process.

Juicy Beerfest
Photograph: Courtesy Unsplash/Evan Dvorkin

9. Juicy Beerfest

Things to do Festivals

IPA and fruited-sour enthusiasts will get satiated at this celebration of beer, with selections from Jupiter’s Civil Society Brewing Co., New York’s Finback Brewery, Richmond’s Ardent Craft Ales and many others. Tickets include unlimited tastings and a custom festival glass. If you need to quell your buzz, the pop-up burger joint USBS will be ready to take your order.

Photograph: Courtesy Wigwood

10. Wigwood

Things to do Festivals

The explosive queer festival anchored at Gramps in Wynwood returns for a fourth year. Judging from 2019’s bonkers three-day marathon of “Under the Sea”–themed parties that showcased all-stars from the Magic City’s drag scene and other LGBTQ circles, the 2020 fest is bound to be a wild ride. Locations and times TBA

Celine Dion
Photograph: Courtesy Wikimedia Commons/Anirudh Koul

11. Celine Dion

Things to do Concerts

For the first time since 2009, Canadian icon Dion has relinquished her record-setting Las Vegas residency and hit the road: Her Courage World Tour swings by Miami this winter.

Coconut Grove Arts Festival
Photograph: Courtesy Coconut Grove Arts Festival

12. Coconut Grove Arts Festival

Things to do Festivals

Coconut Grove comes alive with music, food and art for the three-day Coconut Grove Arts Festival. This family-friendly outdoor event is a great way to spend Presidents’ Day Weekend. Peep work from over 360 artists while you stuff your face with local bites.

New Order
Photograph: Stéphane Burlot

13. New Order

Things to do Concerts

On the heels of last year’s epic sold-out show at the Fillmore, new-wave heroes New Order return to Miami to escape the English cold and play an unprecedented four-night residency at the historic aforementioned venue.

Calle Ocho Festival
Photograph: Courtesy CC/Flickr/Bob B. Brown

14. Calle Ocho Festival

Things to do Festivals

Ten stages with a variety of live performances, drunken revelers reppin’ their country’s flag and all the croquetas and arepas you can stuff into your face. It’s time for Miami’s massive street fair, Calle Ocho, where thousands of people gather across the iconic 20 blocks every year to celebrate Latin pride. It is truly a celebration of everything that makes Miami special. Don’t miss it. SW 8th St between SW 12th and 27th.

AmericanAirlines Arena
Photograph: Courtesy CC/Flickr/HumongoNationphotogallery

15. Farruko

Things to do Concerts

The rising Puerto Rican talent is defining a new generation of reggaetonistas by moving away from trap to incorporate more reggae stylings and a vision of the Caribbean where peace, love and all the weed you need are a way of life.

Pegasus World Cup Invitational
Photograph: Courtesy Pegasus World Cup

16. Pegasus World Cup

Things to do Sport events

The million dollar horse race ($9 million, to be exact) comes to Gulfstream Park. Not into horses? Come for the atmosphere, which, if similar to year’s past, will likely border on South Beach nightclub thanks to a day party hosted by LIV’s David Grutman plus food and beverage offerings from his luxe eateries Komodo, Swan, Bar Bevy and Papi Steak. Details on 2020’s entertainment to come. 

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