50+ Things to do for Labor Day Weekend In Orlando 2019

Labor Day Weekend in Orlando

Summer’s final long weekend is in our sights. What will you do with your three days of relaxation? Labor Day signifies the end of summer for many, and whether you are looking for a relaxing weekend to reconnect with your love, or a last hoorah for the summer, we’ve got you covered! Check out our full guide to Labor Day Weekend in Orlando, from lazy weekend ideas to activity ideas, weekend events and staycation deals.



BBQ Basket Picnic
Preorder by September 1, pick up on September 2
The Ravenous Pig
Devour scratch-made BBQ at your favorite park, pool or beach. The basket feeds 2 people and includes bacon cheddar dip, BBQ beef ribs, marinated chicken skewers, sweet pound cake and Lardermelon beer for you and your honey. 
$75, order by calling 407-628-2333

The Basket at Wine Bar George 
Make your own basket with any of the items on their menu. If you spend at least $60, the basket, silverware, wine glasses, and carafe will be included at no extra cost. To make this even more romantic, walk across from Wine Bar George to the boat dock and head to either Old Key West or Saratoga Springs Resort for a picnic. The boat ride is free for all guests and will provide you with a more secluded location for your picnic date.

For the ultimate lazy picnic date, check out Our Dream Date which offers full-service themed picnic packages including elaborate setups, snacks, drinks and more.

Labor Day in Orlando
Picnic Basket from Wine Bar George. Image credit: Serena Lyn


Labor Day Weekend Poolside
August 31 – September 2
Grande Lakes Orlando
One of our favorite Orlando staycations, Grande Lakes (home to JW Marriott Orlando and The Ritz-Carlton Orlando) will be providing the perfect relaxing vibe all weekend long with drink specials, live entertainment and more. Festivities will be taking place at the Ritz-Carlton Main Pool and the JW Marriott Pool Deck. There will be a fireworks display over Grande Lake at 9pm on Sunday, September 1, for resort guests or those dining at PRIMO. Please note all Labor Day weekend festivities are for resort guests only. Book a staycation with rates beginning at at $159/night at JW Marriott and $265/night at the Ritz-Carlton

JW Marriott Orlando, Grande Lakes


À La Cart is hosting a chill Yacht Rock Patio Party Friday, August 30 perfect for kicking off a leisurely long weekend. Besides jamming to some killer yacht rock tunes, craft beer will be available from Tampa Bay Brewing, Big Storm, Central 28, Elysian, Goose Island, and Veza Sur. Other perks include food for purchase from the five on-site food trucks, plus brewery swag raffles.


Hilton Orlando has a fantastic deal right now on Groupon where you can book a spa treatment at Eforea Spa for a fraction of the cost and enjoy a lazy pool day. You can select from either a 50-minute relaxation massage or a 50-minute custom facial for $109 (regularly $200). After your treatment, head out to the resort’s amazing pool, lazy river, adults-only quiet pool and waterslide. Servers from the pool bar will take your order right from your poolside lounger, and the Groupon includes a free poolside beverage (up to $15). The offer also includes valet parking. FYI: a 20% gratuity will be charged after your treatment.

Want to make it an overnight? Hilton Orlando has Orlando Splash rates available from just $115/night through Labor Day.

Check out our guide to Orlando resort pools you can use with spa and day passes for more spa and pool day combos.

Lazy labor day ideas
Frosé at Hilton Orlando. Image credit: Stephanie Patterson


Rather than coordinating your own DIY brewery crawl, let someone else do all the work for you (including transportation) by joining one of Hop On’s brewery tours of Orlando. Each tour includes round trip bus transportation to multiple breweries, a tour guide, and special beer pricing at each brewery for $38/person. Multiple routes are available all weekend long, visiting breweries like Castle Church Brewing, Crooked Can, Suncreek Brewery, Hourglass Brewing, Ivanhoe Park Brewing and more. 


Pack snacks, blankets and chairs and head out for a romantic movie under the stars with minimal effort. 

Silver Moon Drive In
Daily, 8:45pm & 11pm
Each screen plays a double feature daily, with the first movie staring at 8:45pm, and the second starting around 11pm. Tickets are only $6 and allow you to view both features, so bring a blanket, wine and some take out or snacks and cuddle up to your honey!

Old Town Kissimmee Family Movie Night: Herbie: Fully Loaded
Sunday, September 1, 7pm
Sunday nights are movie nights at Old Town with a family-friendly showing happening weekly at 7pm. These are free to attend, but be sure to bring chairs and grab snacks from the nearby vendors to complete your viewing experience. Labor Day Weekend’s showing will be Herbie: Fully Loaded.

Movie Monday – There’s Something About Mary
Monday, September 2, 7:45-10pm
À La Cart
Head to the Milk District for this free showing of There’s Something About Mary on the lawn of À La Cart. There will be 5 food trucks on hand when hunger strikes, in addition to a selection of beer, wine, andn non-alcoholic beverages. Some seating is provided, but we recommend bringing chairs.
FREE Admission, food and drink prices vary.

Outdoor Movies in Orlando - Movie Mondays at A La Cart
Image credit: A La Cart


Nothing says lazy quite like floating down a lazy river or natural spring in an inner tube. Local resorts with epic lazy rivers (available for resort guests) include Hilton Orlando, JW Marriott Orlando Grande Lakes, Hilton Orlando Bonnet Creek, Reunion Resort, Omni Orlando Resort at ChampionsGate, and Wyndham Grande Orlando Resort Bonnet Creek.

If you’d rather tube down a natural cold spring with crystal clear water, check out Blue Spring State Park, Kelly Park, or KP Hole. At the latter, your float will last 4-4.5 hours!


An excellent way to get acquainted with all the beauty Winter Park has to offer is by hopping on the Scenic Boat Tour. For decades this tour has taken locals and tourists around the Winter Park Chain of Lakes, by Kraft Azalea Gardens, Rollins College, and even past Mr. Roger’s former home. The cost is $14/person. After a relaxing brunch on Park Avenue, hop on the next tour and enjoy the ride, along with some great Winter Park history.

Winter Park Scenic Boat Tour | Photo by Editor Stephanie Patterson


  1. Go zip lining
  2. Try paddleboarding
  3. Visit a Farmer’s Market (Maitland, Winter Garden, Lake Eola, Winter Park)
  4. Check out the The Wheel at ICON Park
  5. Go on a walking food tour 
  6. Visit Bok Tower Gardens… finally!
  7. Go kayaking in a clear kayak
  8. Cool off at Universal’s Volcano Bay
  9. Plan a mini-putt tournament at one of our best putt putt courses
  10. Hang out at Wekiva Island
  11. Make your own pancakes at De Leon Springs
Making pancakes at De Leon Springs
De Leon Springs | Image credit: Hannah Green

12. Tackle the Disney Springs Flavors of Florida food crawl
13. Rent bikes to explore the West Orange Trail
14. Go on a private horseback trail tide for two
15. Check out an Escape Room game
16. Visit Nona Adventure Park and then do a Lake Nona food crawl


Visit Orlando’s Magical Dining
August 23 – September 30
Over 120 local restaurants
Now in its 14th year, Visit Orlando’s Magical Dining Month returns in just a few weeks for a 5-week showcase of over 120+ local restaurants. Running from Aug. 23 through Sept. 30, 2019, it’s your chance to enjoy three-course, prix-fixe dinners at more than 120 of Orlando’s best restaurants for just $35 per person. Plus, through Visit Orlando, $1 from each meal served will benefit one or more deserving local charities.
$35/person prix-fixe menu at participating restaurants

Visit Orlando Magical Dining
The H Cuisine. Image credit: Arlene Laboy

Epcot International Food and Wine Festival
August 29 – November 23
$99 theme park admission, food and drink extra (check out our festival tips from top Disney bloggers!)

Boxi Park’s Labor Day Weekend End of Summer Bash
August 29 – September 2
Boxi Park
Celebrate Labor Day Weekend with live music and drink specials from Boxi Park’s vendors.
FREE Admission, food and drink prices vary

8th Annual ‘Great Irish Hooley’ Music Festival
August 30 – September 2
Raglan Road
A boutique Irish music festival with a colorful live playlist of traditional Irish, Celt grass, folk, blues and soul. The festival will also include Celtic face painting, Hooley-crafted cocktails plus creative new bites by the pub’s inventive culinary team. The pub also will introduce a new local craft beer collaboration with Crooked Can Brewing: the Devil’s Foot Blackberry Golden Ale. And Raglan Road also will serve the delicious Rollicking Raglan Brunch Saturday, August 31 through Monday, September 2.
FREE Admission, food and drink prices vary

St. Patrick's Day in Orlando
Raglan Road Irish Pub

Songs At Sunset: David Mander
Friday, August 31, 6-9pm
Nona Adventure Park
Songs at Sunset is a weekly event series featuring sunsets accompanied by live music.
FREE Admission

Bacon Day Beer Pairing
Saturday, August 31, 5:30pm
Deviant Wolfe Brewing
August 31st is International Bacon Day and what better way to celebrate than with a bacon and beer pairing. The Tennessee Truffle has created a wonderful bacon concoction appetizer that will be paired with a Deviant Wolfe Brewing beer flight.
FREE Admission, food prices vary

Saturday, August 31, 5:30pm
East End Market
A chef’s choice celebration of the varied cuisines experienced on the salty Pacific shoreline, mountainous Andean region, and lush Amazon rainforest with influences from Peru’s diverse immigrant roots. Hosted by PAPA LLAMA. 

Orlando Pride vs. Washington Spirit
Saturday, August 31, 7:30pm
Exploria Stadium
Tickets start at $21

Bioluminescence Paddleboard Tour
Saturday, August 31, 9-11pm
Manatee Cove Park
This 90-minute night paddle on the Space Coast will surely be memorable. The beautiful trail of light is created by tiny natural organisms called dinoflagellates that thrive during the warmest summer months, making this a seasonal tour.

Yoga in Lake Eola Park
Sunday, September 1, 11am
Lake Eola Park
Northeast corner of the park near Panera Bread
$5 cash

Sunday Funday Brunch Food Tour in APGD
Sunday, September 1, 11am
Audubon Park Garden District
This 3-hour adventure will take you on a culinary road trip around the neighborhood to sample the best brunch/lunch items the district has to offer – plus a little history, shopping, and sipping along the way.

Labor Day Soiree on Sunday at Celery City Craft
Sunday, September 1, 2pm
Celery City Craft
Celery City Craft is throwing a Labor Day party featuring live music, drink specials and food trucks starting at 2pm.
FREE Admission

Labor Day at Highball & Harvest
Sunday, September 1, 5:30-9pm
To celebrate Labor Day, Highball & Harvest will be serving holiday inspired dishes paired with cocktails from 5:30-9pm. Enjoy an a la carte menu as well as holiday-inspired dishes paired with hand crafted cocktails from 5:30 – 9 p.m. on Sunday, September 1. As an added bonus, you’ll get to watch a fireworks dispaly over the Grande Lake at 9pm.
Food prices vary. Reservations required, call 407-393-4648.

Labor Day Weekend in Orlando at Highball & Harvest
Image credit: Highball & Harvest

Freestyle Explosion 2
Sunday, September 1, 6pm
Hard Rock Hotel Daytona Beach
This concert will feature 7 live performances from Freestyle entertainers such as Al Bandiero and Frankie Cutlass.

Labor Day Dinner at PRIMO
Sunday, September 1, 6-9pm
Celebrate Labor Day with an a la carte menu of locally sourced, sustainable seafood as well as dishes created from the onsite Primo garden. Pair Chef Melissa Kelly’s imaginative organic cuisine with hand-crafted cocktails and selections from the upscale wine list.
Food prices vary. Reservations highly recommended, call 407-393-4444.

Labor Day Weekend White Party
Sunday, September 1, 7pm-2am
Howl at the Moon Orlando
Dress to impress in all white and get ready to dance the night away! Drink specials include $4 Bud Lights, White Claw Hard Seltzers and Bon & Viv Grapefruit Hard Seltzers, and $25 86oz. Get Lit buckets.
Wear all white for free admission

A Gatsby Evening at The Edison
Sunday, September 1, 7:30pm
The Edison
Get decked out in your finest 1920s attire and enjoy flying aerial champagne performers, a live band, cigar rollers, burlesque dancers, stilt-walkers and more. Guests can sip on complimentary Moet Champagne, and The Edison’s full food and beverage menu will be available for purchase.
$79/person, ages 21+

Labor Day Bottomless Brunch
Monday, September 2nd, 11am-3pm
Mia’s Italian Kitchen
To celebrate Labor Day Weekend, Mia’s Italian Kitchen is extending their weekend bottomless brunch to include Monday, too! Enjoy all of your favorite brunch dishes for only $26/person, and add bottomless mimosas for $16/person.

Disney Springs Flavors of Florida Self Guided Food Crawl
Through September 2
20 Participating Disney Springs Restaurants
Eat your way through Disney Springs while tasting how they interpret Florida Flavors! You’ll find dishes utilizing citrus flavors, fresh seafood, inventive cocktails and desserts inspired by The Sunshine State. Pick up a free event guide at the Welcome Center so you can plan out your crawl.

Disney Springs Jock Lindsey's Hangar Bar wings
Jock Lindsey’s Hangar Bar Fountain of Youth Wings. Image credit: Arlene Laboy

Thai-American Cookout
Monday, September 2, 4-7pm
Whippoorwill Beer House & Package Store
Bangrak Thai Street Kitchen and Swine & Sons will be popping-up and cookin’ up a whole hog.
FREE Admission; food and drink prices vary

Drink n’ Think Trivia
Monday, September 2, 7pm
Orlando Brewing
Test your knowledge and enjoy a night with good friends, plenty of beer, and a chance to win. All trivia players can take advantage of happy hour prices, and winner(s) receive $25 Orlando Brewing gift card!
FREE Admission, drink prices vary

Free Admisson to Harry P. Leu Gardens
Monday, September 2, 9am-5pm
Leu Gardens
Head to Audubon Park and take a leisurely stroll around this beautiful botanical garden, free of charge on Monday, September 2.
FREE Admission


Hyatt Regency Grand Cypress & Hyatt Regency Orlando
Here’s an example of pre-planning coming in handy! Book your stay by August 27 for stays before September 2, 2019 and you’ll receive up to 20%.

Reunion Resort
Reunion Resort is offering an ‘End of Summer’ staycation deal for those wanting to get one last summer escape. For stays through September 15, you’ll receive 10% off 1-bedroom villas or 15% off 2- and 3-bedroom villas. Labor Day weekend activities include a weekend pool party and cookout, a patriotic foot golf challenge, water park activities, spa specials, a family pizza night and more.

Reunion Resort

The Alfond Inn
The romantic ‘Summer Memories’ package includes a fruit and cheese basket, wine for 2, two tickets for the Winter Park Scenic Boat Tour, and complimentary valet parking starting at $249/night. This special runs through October 1, 2019, and is subject to availability.

Omni Orlando Resort at ChampionsGate
The Love and Luxury package includes luxurious accommodations, 2 welcome mini bottles of Moet & Chandon Champagne with chocolate covered strawberries, romantic turndown service, hotel representative pre-call to assist with special romantic requests and late check out at 1pm based on availability. Rates begin at $184/night.

Waldorf Astoria Orlando
Summerblast continues through Labor Day weekend with specialty dining experiences, activities, and family fun every weekend. Activities include s’mores, build your own poolside cocktail, a spa happy hour, poolside yoga, Bar du Chocolat and more. Rates for Labor Day weekend begin at $199/night plus resort fee.

Hilton Orlando
Take advantage of ‘Orlando Splash’ rates from $115/night through Labor Day. Resort activities include s’mores by the pool, poolside activities, a weekend tiki hut and more. Check out the full activity guide here.

Rosen Plaza Hotel
Stay at the Rosen Plaza and take advantage of their ‘Summer Special with Breakfast’ promotion, with rates starting at $103/night for Labor Day weekend. The special also includes no resort fees using promotional code SUMMER.


Feature image credit: Grande Lakes Orlando

Disclosure: Some, but not all of the events and activities mentioned in this post are from our valued advertising partners.