Best of May: 45+ Orlando Events for Date Night This Month

Orlando events - Frontyard Festival series at Dr. Phillips Center

Our monthly curated guide to the best Orlando events for couples


Ready to have some fun in the sun? From the return of the one-of-a-kind Orlando Fringe Festival to multiple outdoor movie nights and performances under the stars, we are excited to enjoy fun events all month long. Here's our curated list of the best Orlando events during the month of May.

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May 1 – 2

Run for the Rosés
Saturday, May 1, 2pm
Hampton Social
Big hats, summer dresses & seersucker suits…time to talk derby at The Hampton Social's Run for the Rosés Viewing Soiree in Orlando. Food and drinks will be available for purchase.
FREE Admission

Orlando events May 2021 - The Hampton Social Orlando Derby Party

The Color Run Orlando
Saturday, May 1, 8am
Osceola Heritage Park
The Color Run is a five-kilometer, untimed event. At each kilometer mark, Color Runners are doused from head to toe in a different colored powder.
$20 and up

St. John's River Festival of Arts
May 1-2
Historic Downtown Sanford
See Art-in-Action from live artist demonstrations and create your own piece of artwork at workshops scheduled during the weekend, plus view art, listen to live music and enjoy gourmet tastes.
FREE

Orlando Taco Week
Through May 4
Participating locations
15 days of $5 taco specials in local restaurants, eateries, taco joints and taquerias.
Menu prices vary

May 3 – 9

Cinco de Mayo Party at Boxi Park
Wednesday, May 5, 6-10pm
Boxi Park
This 21 and older event includes a welcome cocktail, live music, food and drink specials and more!
$20

Little Shop of Horrors
May 5 – 23, various times
Walt Disney Ampitheater at Lake Eola
In an outdoor performance at Lake Eola Park, this campy Broadway and Hollywood sci-fi smash musical stars a lonely florist and his man-eating plant. Read more about this upcoming show here.
Tickets start at $27

Image credit: Orlando Shakes

1st Thursdays at OMA: Nerds in the Age of Popularity
Thursday, May 6, 6pm
Orlando Museum of Art
Discover local artists, listen to live music and mingle with an eclectic mix of people at this monthly curated art show. Each month features a unique theme.
$15

Leu Gardens Movie Night: Wonder Woman 84
Friday, May 7, 8:30pm
Leu Gardens
Enjoy an outdoor movie with your favorite date. Pack a dinner picnic basket and seating, alcohol is permitted.
$6

Orlando Gay Chorus: One Nation, Indivisible
Friday, May 7, 7pm
Dr. Phillips Center for the Performing Arts
Join the Orlando Gay Chorus to celebrate the individual threads that together form the tapestry that is America. 
Tickets start at $24.50

Movieola: Jumanji
Friday, May 7, 8pm
Lake Eola Park
Bring your blankets, chairs and snacks for the movie screening of Jumanji: The Next Level!
Free

Sunset Sessions at the Bohemian Terrace
Friday, May 7, 6-10pm
Grand Bohemian Hotel Orlando
Rooftop concert series featuring live Brazilian jazz music by the Gilberto Santos Band, along with elevated bar bites and drinks. Tickets include an open wine bar and one featured cocktail.
$45

Sanford Historic Garden Tour
Saturday, May 8, 9am
Sanford Residential Historic District
Tour eleven of Sanford Historic District’s most beautiful gardens.
$10

Paws in the Park
Saturday, May 8, 10am
Lake Eola Park
Orlando's Largest Pet Festival in support of Pet Alliance of Greater Orlando, the region’s oldest and largest animal welfare agency.
Register for $15

Kids Night at the Museum
*FEATURED EVENT*
Saturday, May 8, 6-10pm
Orlando Science Center
Enjoy a stress and child-free evening on the town while children have an entertaining experience of their own exploring the wonders of everything the Science Center has to offer. Throughout the night, children will explore exhibits, experience enhanced science programming, and enjoy dinner* and a film. They will also participate in hands-on activities, and see an interactive live science show.
$75 for first child, $40 per additional sibling

Orlando events - Kids Night Out Orlando Science Center
Image credit: Orlando Science Center, photo by Roberto Gonzalez

Date Night at Pig Floyd's
Saturday, May 8, various pickup times available
Pig Floyd's Urban Barbakoa
On the 2nd Saturday of each month, pick up a special date night kit from Pig Floyd's! This month's Date Night Kit (for two) will include: 4 Tacos, 3 Sides & 2 Beers or 1 Wine (equal to two glasses) from Pig Floyd's. You'll also get a scented candle from The Solo Candle, a sweet treat from a local spot, disposable tableware for two and a conversation card. Preorder by calling 1.833.PIG.LOVE. Read more about this date night kit here.
$44.99/couple

Rock the Beach Tribute Band Series
Saturday, May 8, 7pm
Hard Rock Hotel Daytona Beach
Enjoy a tribute to KISS. Tickets include general admission, complimentary valet and one drink ticket.
$10

Daytona Beach
Photo credit: Hard Rock Hotel Daytona Beach

Kevin Smith
Saturday, May 8, 7:30pm
Dr. Phillips Center
Enjoy this outdoor comedy show with Silent Bob himself. 
Tickets starting at $35

Interactive Movie: The Sound of Music
Sunday, May 9, 7:30pm
Garden Theater
Interactive Movies feature pre-show games, trivia, and costume contests hosted by live actors.
$15

May 10 – 16

Diverse Word Open Mic
Tuesday, May 11, 7:30-10pm
Downtown CREDO North Quarter
Diverse Word is the longest running open mic in Orlando. Attend to perform and/or listen to poets and other artists every Tuesday night!
FREE Admission

BBQ Around Orlando
Wednesday, May 12
Participating restaurants
In Memory of Chef Chuck Cobb, join local Orlando Restaurants for their bbq specials on this one day only event. Each participating restaurant will feature one dish/drink. The proceeds from this dish will go directly to Chuck’s wife and four children.
Menu prices vary

Image via Hunger Street Tacos

Corks and Forks Maitland
Thursday, May 13, 6pm
Venue on Lake Lily
An evening of mouth-watering bites and signature dishes from the area's finest local chefs, plus fine wines, spirits, beer and live music.
$45 and up

Thornton Park District 2nd Thursday Wine & Art Walk
Thursday, May 13, 6:30pm
Thornton Park District
Orlando's favorite reoccurring art night, with 22 places to stop for a tasty libation along with art vendors, live music, DJ, artists and all sorts of fun! The cost of admission grants you a wristband glass and a map of all the participating drink locations.
$10

Heather Thorn and Adrian Cunningham in Concert
Friday, May 14, 7pm
Timucua Arts White House
World-class reedman Adrian Cunningham joins xylophonist Heather Thorn with Greg Zabel-upright bass and Bobby Koeble-guitar!
Tickets start at $18

Golden Gals Live
May 14-15, various times
Clermont Performing Arts Center
Your favorite Miami residents, with a drag twist, are coming to the Clermont Performing Arts Center for two performances this May.
Tickets start at $27

Gatorpalooza Fun Fest 2021
May 15 – 16
Gatorland Orlando
Included with park admission will be live music, different food offerings, artisans, craft vendors, family fun, games, appearances by the Gatorland Vlog Team and, of course, all the alligators, animals and awesomeness that a day at Gatorland has to offer. Gatorpalooza attendees will enjoy a zany Gator Man Challenge contest on Saturday and a Turkey Dog Toss Contest on Sunday, with guests tossing turkey dogs to Gatorland personalities in boats in the Alligator Breeding Marsh.
Included with park admission; $14.99 for Florida residents the entire month of May

Sushi Rolling Class
Saturday, May 15, 2-4pm
Orlando World Center Marriott
Learn how to roll sushi like the pros with a hands on sushi rolling class, taught by the resort chefs. Class includes two rolls.
$25

Viva La Musica
Saturdays and Sundays May 15 – 23, 12pm-close
Sea World Orlando
Experience all the color and culture in a new way as this festive, family-friendly Latin celebration returns. Viva la Música is included with park admission.
Included with park admission

Looking for more date night ideas along I-Drive? See what else is on the calendar this May on I-Drive.

Central Florida Film Slam
Sunday, May 16, 1pm
Enzian Theater
Held six times a year, the Central Florida Film Slam is an unrated, independent film showcase and competition open to all regional filmmakers and students.
$9

en el jardín [in the garden] – Mexico
Sunday, May 16, 2-4pm and 4-6pm
Emeril Lagasse Foundation Kitchen House & Culinary Garden
Join local chefs and artisans for a look into the cuisine of Mexico for this exclusive event! Stroll around Edible Education Experience’s garden as you sip on delicious margaritas and enjoy delicacies ranging from the city to the country. Learn about the different regions of Mexico, all while experiencing College Park’s hidden gem. Read more about this event here.
$5; food and drink available for purchase

In the Garden food series - Mexico - Orlando events
Image credit: Edible Education Experience

Disney Movie Night: Up
Frontyard Festival at Dr. Phillips Center
Sunday, May 16, 7pm
A dash of magic comes to downtown Orlando nearly every Sunday evening as Dr. Phillips Center presents Disney Movie Night—classic stories direct from the Walt Disney Company’s vast film library.
$5 – $10

May 17 – 23

30th Annual Orlando International Fringe Theatre Festival
May 18 – 31
Loch Haven Park
14-day art festival featuring hundreds of shows throughout multiple venues in Orlando’s Loch Haven Park. Shows range from comedy to burlesque, music to drama, and everything in between.
$10 Fringe button; most shows $12 each

Sunset at the Zoo
Thursday, May 20, 5-8pm
Central Florida Zoo
Enjoy adults-only access to the zoo during sunset with food + adult beverages for purchase.
$7

3rd Thursday at CityArts
Thursday, May 20, 5-9pm
Downtown Arts District Orlando
Art exhibits throughout downtown Orlando.
FREE

Chateau Saint Cosme Wine and Cheese Tasting
Thursday, May 20, 6:30pm
The Wine Room on Park Avenue
Join us as we tour through Chateau Saint Cosme wines paired with delicious cheeses! Reserve your Virtual Kit today, and enjoy our tasting from the comfort of your own home!
$55 per couple

An Evening in Spain

Friday, May 21, 6:30-9pm
Art & History Museums of Maitland
This exhibition opening event will feature a performance by Flamenco del Sol, music by contemporary flamenco guitarist Don Soledad, passed tapas by John Michael Exquisite Weddings & Catering, plus a cash bar with sangria & other libations, as the campus is beautifully lit for your stay-cation to Spain.
$5

Create Your Own Botanical Lotions
Saturday, May 22, 9:30am-12pm
Leu Gardens
Use calendula flowers to create your own botanical lotion in this guided workshop. All materials provided but please bring your hand clippers to class, if you have them, and wear appropriate garden clothes.
$35

Porch Stock – 4 Porches of Peace & Music
Saturday, May 22, 6-10pm
Colonialtown North
This Band Crawl will take you around the hood to hear live bands play on 4 porches throughout the evening. At each porch, groovy refreshments will be provided.
FREE

M&M Latin Jazz Ensemble
Saturday, May 22, 7pm and 9pm
Dr. Phillips Center
This unique and energetic musical group plays original compositions, re-invented Jazz Standards, and selections from the American songbook, all with a Latin flavor!
Tickets start at $35

Bad Witch Burlesque: LOVESPELL
*SOLD OUT*
Saturday, May 22, 8:30pm
ME Performing Arts
With love, thought and care we have created a jaw dropping show filled with burlesque, live musical acts & aerial arts. Set to our FAVORITE genre of music ROCK & ROLL! This romantic, rock infused, LIVE burlesque experience will truly leave you under our spell!
$25

May 24 – 31

Wild Florida's Gator Week
May 24-29
Wild Florida
Enjoy a week full of gator-themed activities and demonstrations. Wild Florida will also be offering everyone free admission to the Gator Park during Gator Week.
FREE admission

Image credit: Wild Florida

 

Seaside and Scotch
Tuesday, May 25, 6:30pm
The Osprey Orlando
Featuring cocktails and tastings from Compass Box Scotch, Chef Cooper will present a seaside-inspired seven-course menu. 
$125 

France Discovered Wine Course
Wednesday, May 26, 5:30pm
College Park Emeril Lagasse Foundation
Explore the France Wine Country on this guided wine tasting and course.
$150

Popcorn Flicks in the Park: The Apple Dumpling Gang
Thursday, May 27, 8pm
Central Park – Winter Park
Enjoy a free outdoor movie in Winter Park's Central Park every month as part of this ongoing free outdoor movie series. Reservations are required and can be made here starting April 1.
FREE; reservation required

Freestyle Fever Summer Dance Party
Friday, May 28, 6pm
Hard Rock Hotel Daytona Beach
Make your way to the oceanfront Avalon Terrace for a freestyle summer dance party by the beach! Featuring performances by your favorite freestyle artists and DJs. 
$40

The Foreigner – A Culinary Experience
Friday, May 28, 7:30pm
The Heavy
Bruno and team will present a 5 course omakase style dinner with a contemporary approach to food & wine, and an opportunity for you to allow them to take you through a journey of elegant flavor, in Winter Park.
$110

Classic Albums Live: Tom Petty
Friday, May 28, 8pm
Hard Rock Live
Classic Albums Live features the finest studio musicians performing classic rock albums LIVE note for note, cut for cut. This time it's Tom Petty's “Damn The Torpedoes”!
Tickets start at $35.50

Vertical Concert Series: Easy Posse + Garth Brooks Tribute
May 28 – 30, 8pm
Orlando World Center Marriott
The series will feature a different band every weekend that will perform on Friday and Saturday night and will culminate with a nightly laser show. Bands will be featured on the upper pavilion, viewable from the private balconies of the guest rooms surrounding the area. Over Memorial Day Weekend, celebrate with a long weekend featuring 2 bands over 3 nights and a spectacular firework display on Sunday night to end the weekend festivities.
*Overnight stay required; packages from $254/night

Fireworks at Orlando World Center Marriott

Rock N' Blues Concert & Car Show
Saturday, May 29, 4pm
Lake Concord Park
View more than 100 classic cars ranging from Camaros to Chevelles to Mustangs, plus food trucks and live music. 
FREE Admission

Five Years After the Pulse Tragedy
May 29 – August 15
Orange County Regional History Center
The Orange County Regional History Center’s 2021 remembrance exhibition, Community: Five Years After the Pulse Tragedy, examines how communities of all kinds were touched both locally and across the globe. Visitors will follow the story of Pulse nightclub, from its earliest conception through 2016, as well as the response to the devastating event and the lasting impact in the time since. Through the telling of this important part of our collective history, the museum seeks to celebrate the spirit of community and honor the 49 victims and all of those affected.
$8

Bachata Brunch ft. Bachata Heightz
Sunday, May 30, 1pm
Dr. Phillips Center
Bachata Heightz is an urban-influenced bachata group from New York whose debut single, “Me Puedo Matar,” was a big hit on the tropical charts in 2009. Enjoy the show while also enjoying brunch.
$15 for entry, food sold separately

Ongoing Orlando Events

Flavors of Provence
Tuesdays through May
Vinia Wine & Kitchen
Specialty 3-course menu featuring the French flavors of Provence, expertly paired with wines. Call or text (407) 925 7485 for reservations as seating is limited.
$49; additional $35 for wine pairiings

Spring U-Pick at Southern Hill Farms
Select dates through May
Southern Hill Farms
Pick your own peaches, blueberries, sunflowers and zinnias at this family farm in Clermont. Read more about spring u-pick here.
FREE Admission; u-pick and food prices vary

Southern Hill Farms blueberry donuts and frozen blueberry lemonade

TPD Thursday Night Market
Thursdays from 6-10pm
Thornton Park District
A family and dog friendly weekly outdoor market! Located by World of Beer in the Osceola Circle. Featuring unique local vendors, food trucks, music, bars provided by Aku Aku Tiki & The Abbey and lots of outdoor seating!
FREE Admission

Public Ice Skating Sessions
Various Dates
RDV Ice Den
Enjoy public skating on the ice rink every week!
$13

Bites, Sips and Hips
Fridays and Saturdays, 9pm
HÄOS on Church
Dine and Enjoy a DAMN GOOD SHOW with Blue LaLa Entertainment. Come see what Orlando is talking about! Reservations recommended.
$7 artist fee upon arrival; menu prices vary

Weekends at the Winery
Saturdays and Sundays through May
Lakeridge Winery
Come out and enjoy the expansive vineyard green, including delicious food, live entertainment, and Lakeridge wines by the glass at the outdoor bar. Bring your own lawn chairs.
FREE Admission

Craft Beer and History Tour
Saturdays in May, 3pm
Historic Downtown Sanford
This popular guided experience provides you the opportunity to experience the district’s popular east side craft breweries while learning about the city's tumultuous history of prohibition in Sanford, FL.
$35

Seven Seas Food Festival
Weekends through May
SeaWorld Orlando
Roam the expansive open-air grounds and embark on an international flavor journey inspired by the tastes and smells of the Caribbean, Italy, Brazil, Asia and beyond.
Included with park admission; food prices vary

Wine Quest’s 25th Anniversary Celebration
June 4, 7-10 p.m. and June 5, 6-10 p.m.
Quest, Inc. invites you to celebrate the 25th year of their signature event, Wine Quest! Grab your tickets and enjoy wines from around the world, delight in exquisite cuisine and partake in silent and live auctions! Perfect for a unique date night or fun with friends. Friday, June 4 is the Grand Tasting & Auction. Saturday, June 5 is the Premier Dining Experience. Both nights take place at Loew’s Royal Pacific Resort where complimentary event parking will be available. Cocktail attire. Must be 21+ to attend.


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Disclosure: Some, but not all, of the Orlando events featured in this post are hosted by our valued advertising partners.

Feature image credit: Dr. Phillips Center for the Performing Arts


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