Summer is trying its best to take over! With the heat on the rise, it's a good time to check out our summer date ideas. And if the skies open up, head indoors. Let's take a look at the best events and things to do this week.
Attention Parents: Head to Orlando-Parenting.com for things to do with kids in Orlando.
Featured Events
Giving an extra shoutout to the following AMAZING events which help us to bring this guide to you for FREE!
Father's Day Bourbon Pairing Dinner
Saturday, June 14, 2025 at 7pm
Market to Table: 146 W Plant St., Suite 140, Winter Garden, FL 34787
Market to Table offers intimate, four-course prix fixe dining experiences including curated Dinners with select wines or bourbons to accompany each course. Celebrate Father's Day this year with a special Bourbon Pairing Dinner featuring Citrus Cured Salmon, Roasted Bone Marrow and Smoke Beef Tenderloin paired with select Bourbons. Finish the night with delectable Chocolate Raspberry Ganache and a French Vanilla Bourbon.
$95++ per person. For more information call (407) 395-9871. Reservations, note “Chef's Wine Dinner” under Additional Requests.
The next Chef's Wine Dinner is Saturday, June 28.
River Country Water Park – NOW OPEN!
Westgate River Ranch Resort
3200 River Ranch Blvd, River Ranch, FL 33867
Get ready for splash-filled adventures at River Country Water Park! Splash through thrilling water slides or take a refreshing dip in the pool. Whether you're soaking up the sun or relaxing poolside, there's no better place in Lake Wales for a full day of fun. Plus, book early at RiverCountry.com and score free water park tickets, making your stay even more unforgettable.
Read More on Westgate River Ranch's Day Passes HERE.
Wild Safari Bourbon & Whiskey Tasting Tour
Friday, June 20, at 7 p.m.
Eola View Orlando
Embark on an unforgettable evening of bold flavors and exotic ambience at Eola View’s Wild Safari Bourbon & Whiskey Tasting Tour. Inspired by the allure of safari, enjoy sample pours from top distilleries, a 30-minute tasting class, live entertainment, and themed décor. Choose from General Admission, Food Upgrade, or VIP with open bar and exclusive swag. Enjoy steel drums, Cuban cigars, and more. Tickets start at $55. Adventure awaits—reserve your spot now!
Things to Do This Week May 26 – June 1, 2025 Orlando Events
DeLand Ice Cream Walk
Friday, May 30, 6-8pm
Downtown DeLand, Woodland Blvd. DeLand, FL 32720
Scoop there it is! Remember when chasing the ice cream truck was the highlight of your summer? Relive the magic—minus the running. We’re talking downtown charm, sweet treats, and that kid-in-a-candy-store feeling (but with fewer grass stains). Bring your besties, your sweet tooth, and maybe a wet wipe. Stay cool. Stay nostalgic. And don’t wear white. Held rain or shine.
$16 for adults, $9 for kids 12 & under
Orlando Critical Mass
Friday, May 30, 6:30pm
Join fellow cyclists for the largest ongoing group bicycle ride through Downtown Orlando. Rides typically are up to 10 miles, rain or shine, and depart from Loch Haven Park.
Free
Michael Jr.’s Funny How Marriage Works Comedy Date Night Experience
Friday, May 30, 7-9pm
Living Water Fellowship, 4101 Pleasant Hill Rd., Kissimmee, FL 34746
This live, faith-based comedy show blends humor and heart to help couples strengthen relationships through laughter and real conversation.
$35.21
Let’s Get Shrekxual: A Swampy Burlesque
Friday, May 30, 8pm
Conduit, 6700 Aloma Ave., Winter Park, FL
For one night only, Conduit will host a sexy burlesque show like none other. Couples can enjoy a whimsical fairytales that embraces the hilarity of a popular green character. One night only.
$15-$30
The 18th Annual Hurricane Party Music Festival!
Saturday, May 31, 12pm-2am
West End Trading Company, 202 S Sanford Ave Sanford, FL 32771
Enjoy a full-day music takeover from Noon to 2AM in Historic Downtown Sanford featuring 20+ EPIC BANDS across 5 STAGES, including ska staples Mad Caddies, high-energy heroes Big D and the Kids Table, and hometown legends The Supervillains! Plus tons of delicious food trucks, local craft beer, cocktails, THC and non-alcoholic beverages, unique vendors, and good vibes!
Starting at $40
Science Night Live
Saturday, May 31, 8pm-11:30pm
Orlando Science Center
Embrace your inner scientist at Science Night Live, an adults-only event at the Orlando Science Center. Explore interactive exhibits, attend live science demonstrations, and enjoy access to the Crosby Observatory for stargazing. It's a night of discovery and fun for the 21+ crowd.
$20
The Pride Cup
Saturday, May 31-Sunday, June 1, 2025
Fairfield Inn Lake Buena Vista
The Pride Cup is a LGBTQ+ multi-sport competition held in alignment with Orlando Gay Days. These events welcome athletes of all levels to participate in friendly competition.
Tournament price varies per sport.
Pizza Shop Rave
Sunday, June 1, 4-8pm
Nuri's Tavern, 63 E Pine St, Orlando, FL 32801
Prolific Entertainment is teaming up with Nuri's Tavern for their first-ever pizza pop-up! Bringing fresh energy to Orlando’s newest local staple — vibes curated by @heyrommii & @okayval, alongside @renomusikk, @yayi.ofc, & @feiloudj. Join this Sunday Funday pizza shop rave!
Weekly Ongoing Orlando Events
2025 Florida Prize in Contemporary Art
May 31-August 24, 2025
2416 N Mills Ave, Orlando, FL 32803
View the eleventh installment of the Florida Prize in Contemporary Art featuring 10 progressive and exciting artists working in the state who range from emerging to having distinguished records of exhibitions. This year's selected artists are: Nathalie Alfonso, Eddie Arroyo, Leo Castañeda, Kelly Joy Ladd, Amanda Linares, Kandy G. Lopez, Jiha Moon, Troy Simmons, Cornelius Tulloch, and Lisu Vega.
AC Orlando Downtown Express Lunch
Lunch served Tuesday-Friday 11am-3pm
333 S. Garland Ave, Orlando, FL 32801
Introducing AC Hotel's new Express Lunch—crafted for those on the go but unwilling to compromise on flavor. For just $18, enjoy a chef-inspired entrée and a non-alcoholic beverage, all guaranteed to be served within 20 minutes of ordering. Perfect for a power lunch or a quick catch-up, it's speed without sacrifice. Available Tuesday-Friday—because great taste shouldn't have to wait.
Singo at Forward/Slash Distillery
The Last Thursday of Every Month, from 7-9 p.m.
650 S Capen Ave, Winter Park, FL 32789
The easiest game you’ll ever play is Singo! Hosted by Challenge Entertainment at Forward/Slash Distillery in Winter Park on the last Thursday of the month from 7PM – 9PM, Singo is a game of zero skill and all luck. Grab a drink, hear a song, and see if it’s on your bingo card. Groups are encouraged and is open to anyone 21+. Next Singo night: May 29th.
Pottery Night
One Thursday Every Month, from 6:30-8 p.m.
8602 Universal Blvd, Orlando, FL 32819
Discover the magic of pottery in this 2-hour group session at the Castle Hotel! Guided by a skilled instructor, you’ll master the basics of throwing clay on the pottery wheel and create your very own unique piece. From shaping the clay to glazing for a polished finish, this experience offers hands-on fun from start to finish. Whether you're a beginner or looking to sharpen your skills, this class is perfect for unleashing your inner artist. Next Pottery Night: May 15th.
Makers Market at Forward/Slash Distillery
The Last Saturday of Every Month, from 2-6 p.m.
650 S Capen Ave, Winter Park, FL 32789
Support your local Orlando makers at Forward/Slash Distillery’s monthly Makers Market. Hosted by Orlando Local Maker’s, this event features the best of vendors who craft and make various items, goods, trinkets, and gifts. The next markets are April 26 & May 31st with the last one of the season hosted in June before a break for summer. Food will be served by Bien Fuego BBQ for some light bites while you shop. Free to attend!
Mermaid Dives and Meet & Greets at SEA LIFE Orlando
Fridays – Sundays, May 3 – 26, plus Memorial Day (May 26, 2025)
SEA LIFE Orlando Aquarium, ICON Park
Mermaids are making a splash at SEA LIFE Orlando every weekend this May. Included with regular admission, guests can watch enchanting mermaid dives in the Atlantic Ocean habitat and meet a mermaid in the magical Mermaid Grotto.
Dive Times:
11:30 AM – 1:00 PM
2:00 PM – 4:00 PM
5:00 PM – 6:30 PM
Meet & Greet:
11:30 AM – 6:30 PM
ICEBAR Orlando Epic Summer
May 15 – September 1, 2025
ICEBAR's summer lineup includes themed cocktails, a liquor-infused ice cream bar, weekend DJs, live ice carving shows, and the brand-new Tiki-themed ICEBAR Beach Club. Enjoy games, giveaways, and lively parties throughout the season.
Bonus: Show your Epic Universe ticket for free entry Sunday through Thursday and half-off entry on Fridays and Saturdays.
Tasty Takeover in The Milk District
Tuesdays from 6:30-10pm
The Milk District – E. Robinson St
THE food truck block party in Orlando! Find it in The Milk District every Tuesday night behind the bars and shops of E. Robinson St.
FREE Admission
Game & Hobby Night at The Burrow
Every Tuesday, 5pm – 8pm
The Burrow Cafe & Play, Mills area
Bring along your favorite game, knitting project, book, or enjoy one of the games available at The Burrow. Come relax, be playful, and enjoy your favorite hobby or discover a new one. Free to attend and drink specials available.
Luminary Market
First Wednesday of every month, 5:30-9pm
Luminary Green Park in Creative Village
Explore 20-25 local vendors featuring unique, curated goods and support our growing community of residents, students, and workers. Stick around after shopping for KaleidoScope 360°, an outdoor movie series where you can enjoy family-friendly films under the stars! Showtime is at 7pm.
Late Night Thursdays
Thursdays, 5pm – 8pm
Leu Gardens
Bring a picnic & seating, sip some spirits, or take a stroll through the gardens and discover the amazing ORIGAMI IN THE GARDEN exhibit. Included with general admission. Rain or shine.
$15 per adult, $10 per child
Piano Bar Show at Jewel
Friday and Saturday Nights
Jewel Orlando
Dueling Piano players take the stage for a fun night of song requests and sing-alongs! Call (321) 444-5306 after 5pm to get your password for speakeasy entry.
FREE admission with password
RELATED: How to Have an Orlando Food Truck Date
Cirque du Soleil “Drawn to Life”
Wednesdays – Sundays
Performances of “Drawn to Life” take place on most nights at 5:30 pm and 8:00 pm. Go for the later show if you prefer to potentially have less kids in attendance. Additionally, it will give you more time to enjoy Disney Springs before the show.
Weekends at the Winery
Saturdays and Sundays, 10am – 5pm (Sat) & 11am – 5pm (Sun)
Lakeridge Winery
Head to this Central Florida winery's expansive vineyard green each weekend for delicious food, live entertainment, complimentary wine tastings/tours, and Lakeridge wines by the glass at the outdoor bar. Plus, delicious food at the Food Pavilion, as well as live music all weekend long.
FREE admission
Check out multiple Farmers' Markets around Orlando every weekend.
Saturday Exhibition Highlights Docent-Led Tour
Every Saturday, 1pm & 3pm
Rollins Museum of Art
Docent-led tours of highlighted works from the season’s exhibitions at the Rollins Museum of Art.
FREE
Tai Chi in the Garden
Every Saturday through 2025, 10:30 am – 11:30 am
Mead Botanical Garden, 1300 S. Denning Dr, Winter Park
A gentle exercise program that is composed of slow deliberate movements, meditation, and deep breathing to enhance health and well- being.
$15
Next Week: June 2-June 8, 2025
Bonsai Workshop
Tuesday, June 3, 7-9pm
RockPit Brewing, 10 W. Illiana St, Orlando, FL 32806
Bonsai Bar, a pop-up with strong date night roots, to host a beginner workshop for creative friends and couples. Enjoy an adult beverage and customize a tiny tree.
Tickets: $85
DIY Beach Towel and Beach Bag
Tuesday, June 3, 7pm
The View, 2601 Clermont National Dr, Clermont, FL 34711
Join Pear Design Studio for the perfect girls' evening or family activity as you create your own custom-designed beach gear! In this fun, hands-on workshop, you'll learn how to transform plain 30×60 beach towels and 20×25 canvas bags into bold, beach-ready accessories using stencils and a simple bleach and paint technique. Get creative, grab dinner from The Marketplace, and your favorite drinks from the Dobel Lounge, and celebrate summer!
Tickets: $40
Paint & Sip at CityArts
Wednesday, June 4, 6:30 – 8:30pm
CityArts, 39 S Magnolia Ave, Orlando, FL 32801
Join City District for a splash of creativity and a sip of inspiration at a Paint & Sip Night in the Downtown Arts District! Hosted at vibrant CityArts and proudly sponsored by Orlando Health, this one-of-a-kind evening blends art, wine and wellness featuring themes of medicine, therapy and music. No experience needed – just bring your imagination and a open mind!
$28.52 per person, includes light bites, drinks, and art supplies
Nikki Glaser: Alive And Unwell Tour
Thursday, June 5, 7pm & Friday, June 6, 9:30 pm
Hard Rock Live Orlando, 6050 Universal Blvd, Orlando, FL 32819
What’s the glue helping couples stick together? Laughter! Chuckling with a romantic partner is a real-deal love potion, according to published findings. Celebrity comedian Nikki Glaser will be in town for two nights to serve up belly laughs like none other.
Tickets: $39.75-$69.75
STOMP
June 6–7, 2025, 2pm & 8pm
Walt Disney Theater at Dr. Phillips Center for the Performing Arts
With the invitation to “see what the noise is all about,” this unique show doesn’t miss a beat with matchboxes, brooms, garbage cans, Zippo lighters, etc. Stomp along to the music and dance.
Tickets start at $40
Love is Universal Nights
Every Thursday and Friday in June
Red Coconut Club at CityWalk
Celebrate Pride Month at Red Coconut Club during Love is Universal Nights every Thursday and Friday in June. The event is for guests 21 and up and features live entertainment, plus specialty drinks available for purchase. Admission is free.
9th Annual CommUNITY Rainbow Run & Festival
Saturday, June 7, 7:30am
Orlando City Hall Plaza,
400 South Orange Avenue, Orlando, FL 32801
More than just a race, this is a celebration of our community’s resilience and love. Run (or walk) to honor and remember the 49 angels, survivors, victims' families and all those impacted by the Pulse tragedy (June 12, 2016).
Summerween Boozy Book Fair & Bingo
Friday, June 6, 7 – 9pm
Spellbound Bookstore, 105 N Oak Ave, Sanford, FL 32771
Browse a table full of spooky books and merch and order the $2 off drink specials at the bar. This will include a refreshing Hibiscus Mojito Cooler and a delicious Berry Zen Sparkler! Sign in for Bingo will be from 7-7:30 and bingo will begin promptly at 7:30PM.
Bingo tickets may be purchased for $12 per card. Event admission is free.
Mark Your Calendar: June 9-15
Gay Men Speed Dating
Thursday, June 12, 2025, 7-9pm
WXYZ Bar at Aloft Hotel
500 South Orange Avenue Orlando, FL 32801
Ever double-booked date night? How about mingling with many potential partners? This organized event is cheeky-chic and fun.
Tickets $33+
DJ Pauly D
Friday, June 13, 2025, 10pm
The Vanguard, 578 N. Orange Avenue, Orlando
OMG! It’s time for GTL in our very own ORL. The beloved Jersey Shore alum, Pauly D, is set to perform late into the night for your delight.
$20-$60
Central Florida Juneteenth Black History Bus Tour
Saturday, June 14, 2025, 8am-5pm
Shiloh Baptist Church
604 W. Jackson St., Orlando
On Juneteenth, a holiday that commemorates the emancipation of enslaved African Americans in Texas on June 19, 1865, this immersive experience aims to highlight the stories of resilience, achievement, and cultural vibrancy that helped shaped Central Florida.
$50
Pride Drag Brunch at Citrus Club
Saturday, June 14, 2025, 11am
Citrus Club, 255 South Orange Avenue #STE 1800 Orlando, FL 32801
Get a taste of glamour and laughter at the Citrus Club Pride Drag Brunch. Hosted by Ranii Ram, with multiple performers.
Tickets $13+
Save The Date
Taste! Central Florida
Saturday, July 12, from 6:30-11 p.m.
Orlando World Marriott Center
Taste! Central Florida is the region’s premier annual culinary and beverage tasting event, bringing together more than 80 of Central Florida’s top chefs, restaurants, and beverage experts for an unforgettable evening to include live entertainment, interactive revenue enhancers and a mission to combat hunger in our community. It stands out as one of the year's major fundraisers for Second Harvest Food Bank of Central Florida, and the Coalition for the Homeless of Central Florida, creating profound awareness and relief for the children in our community who face hunger on a daily basis. Every dollar raised stays within the community, ensuring children in Central Florida have access to the nourishment they need to thrive.
Christner's Prime Steak & Lobster Celebrates 32 Years of Dining
Friday, June 20, 5pm
Christner's Prime Steak & Lobster, 729 Lee Rd, Orlando, FL 32810
The Christner family is celebrating its anniversary on June 20 to honor 32 years of legendary dining in Orlando at Christner’s Prime Steak & Lobster. In addition to myriad charities, foundations, and events supported throughout the years, the family-owned, award-winning restaurant generously opens the doors for a special fundraising celebration dinner to benefit two local charities of choice. 100% of dining proceeds (excluding alcohol sales) will be donated and equally shared between Aspire Health Partners and the AdventHealth Diabetes Institute. Now taking reservations.
Prehistoric Sip & Stroll
Thursday, June 26, 5:30pm – 8pm
Oviedo Mall
Channel your inner T-Rex, and join us for an extinct-level evening of flavor and fun at Oviedo Mall’s Prehistoric Sip & Stroll! Wander the mall on a dino-sized adventure featuring complimentary food & wine tastings, Jurassic photo ops and more.
Costumes and dino-themed outfits are totally encouraged—bonus points if you can sip in a T-Rex suit. Must be 21+ to participate in alcohol tastings.
For even more things to do in Orlando, check out these top stories:
- Best Orlando Spas for Couples
- Orlando’s Most Romantic Restaurants
- New Restaurants and Experiences in Orlando
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