Time To Relax! Our Laziest Labor Day Weekend Date Ideas

Labor Day weekend in Orlando

Our ideal Labor Day Weekend involves as much relaxation as possible! We’ve compiled a list of our laziest Labor Day Weekend date ideas, from a romantic picnic, to tubing and even some staycation deals. Here are a few of our favorites: 


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


Click below for our full guide to Labor Day Weekend in Orlando!

50+ Ways to Celebrate Labor Day Weekend in Orlando

Labor Day Weekend in Orlando

Feature image credit: Stephanie Patterson

Disclosure: Grande Lakes, Reunion Resort and Hilton Orlando are some of our valued advertising partners.


Comments are closed.