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Labor Day 2019 in Miami

Are you looking to visit Miami this Labor Day 2019? View our listings or call 1-844-BOOK-OYO to find available rooms today.

Rumor has it that P.J. McGuire, VP of the American Federation of Labor, thought September 2nd was the ideal date for its near-perfect weather and because it sits midway between Fourth of July and Thanksgiving. Whatever the reason, most of us get one day off to do whatever we want (besides work). With dreamy beaches caressed by surreal turquoise waters, incredible cuisine, and vibrant club culture, Miami may just be one of the best places to forget about your job for a while. Below are our top picks for what to do in Miami for Labor Day.


What better way to explore a city than through its cuisine?

Miami Spice


August 1st–September 30th 

Various locations

Fantastic puns aside, Miami Spice gives you the chance to sample some of the area’s most enticing cuisines. With 215 local restaurants participating, there has to be something you’ll like. Dine on specially priced prix-fixe menus from award-winning establishments like Scott Conant’s Scarpetta.

Wharfin’ Around the USA: Food & Wine Festival

August 30th, 12–3 p.m. 

114 SW North River Drive 

Miami, FL 33130 

(305) 906-4000

Grab some bites and sip on some wine from nine of the country’s greatest cuisine contributors. If the food wasn’t enough, you’ll also have plenty of background music with live performances from Kid Nemesis, Paul E, and Hush Money.

The Dinner Detective

Newport Beachside Hotel 

16701 Collins Avenue 

Sunny Isles Beach,  Florida 33160 

(866) 496-0535

Have you ever wanted a little mystery with your dinner? No, not a mystery meal, but a case to solve as you wine and dine. Grab your spot and be prepared for a killer meal (cue the spooky laugh).


Inhibitions? We’ll see you tomorrow.

Labor Day Weekend Club Crawl 

(305) 842-0937

You may have heard that Miami has a few clubs. No? Well, it does, and they’re a pretty big part of the Magic City’s nightlife. Join the Club Crawl and get dance-worthy perks like VIP entry, premium open bar, and a party bus to take you from Club A to Club Z. 

5th Annual Ball & Chain Music Festival

August 30th–September 1st 

Ball & Chain 

1513 SW 8th Street 

Little Havana, FL 33135 

(305) 643-7820

This iconic Miami music club is hosting a three-day festival, so put on your dancing shoes—there are rugs to cut. Work up a sweat to hits by PALO!, Art Official, and Lemon City Trio. Not much for dancing? Then kick back with a mojito and watch this place come alive.

Labor Day Reggae Splash Festival

September 2nd, 12 p.m.–3 am 

Gro Wynwood 

2700 NW 2nd Avenue 

Miami, FL 33127

If you prefer mellower beats compared to the club-thumping sounds, then this is your jam. Nosh on eats from local vendors, get wet and wild with some water activities, and of course groove to some Rasta vibes from Redlyte, Hymn Marley, and Inner Circle.


Listen to the siren song of big blue and get out on the water.

Private Sailing Trip on Biscayne Bay

Dinner Key Marina 

3400 Pan American Drive 

Miami, FL 33133

Grab some friends and set sail on a 40-ft sailboat for four hours. Bring your own bubbly and toast to the day off with one of the most stunning skylines as your background. Not too shabby.

The Jet Ski Experience in Miami 


1275 NE 79th Street 

Miami, FL 33138 

(305) 814-6884

Hey, sometimes it’s more fun to be the driver than the passenger. Rent some wave runners and feel the wind rushing through your hair as you take in the too-polished-to-be real sights of Miami. 

What’s there to do on Labor Day in Miami? Everything, but if you don’t know where to start, our list should give you some ideas that’ll make your send-off to summer pretty sweet. Whatever you do on Labor Day, make sure you’re living the good life and thoughts of work are far from your mind. That’s what tomorrow is for.

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