Our Favorite Tampa Bay Events for May

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Get out and explore this month with your favorite plus one by checking out one of these top Tampa Bay event picks for date night this May 2022! There’s a lot on our curated guide of things to do, so keep scrolling! It starts with event highlights for things to do this week, followed by our top picks for Tampa Bay events for the rest of the month. You’ll also find an ongoing events section for even more date night ideas in Tampa. Check back often as we add more Tampa Bay events to this listing throughout the month.

For even more things to do in Tampa Bay, check out these trending stories:

For family-friendly things to do in Tampa, check out Tampa Bay Parenting.

Things to Do in Tampa April 30-May 7

Los Vinos de Dalí 2022
April 30
The Dalí Museum
The highly anticipated event features a variety of fine wines, cold craft beers, specialty spirits as well as delectable tastings from top restaurants. During the event, guests may wander the Museum, including an unparalleled collection of Dalí’s works and the special exhibition Picasso and the Allure of the South, enjoy live music and strolling entertainment, and participate in a silent auction and other games of chance including raffles and the popular cork pull.
$120 ($110 for members)

AJR: The OK Orchestra Tour
May 4
MIDFLORIDA Credit Union Amphitheatre
$30.50 and up

The Band’s Visit
May 4-8
Straz Center
With a Tony- and Grammy-winning score that seduces your soul and sweeps you off your feet, and featuring thrillingly talented onstage musicians, The Band’s Visit rejoices in the way music makes us laugh, makes us cry, and ultimately, brings us together.
$36.50 and up

XOXO Carnival
May 4-8
Armature Works
Experience your favorite carnival rides, midway games, tasty treats, and music from acts like Lil John, The Black Honkeys, Shaggy, and Circus Cowboys! From Pied Piper Productions, the XOXO carnival will be filled with over 300,000 square feet of fun for kids and adults.

Jesse James Decker
May 6
Ruth Eckerd Hall
Singer, songwriter, TV personality, fashion designer, beauty and lifestyle influencer/entrepreneur and 2x New York Times best-selling author, Jessie James Decker comes to Clearwater for her Ruth Eckerd Hall debut with special guest, Adam Doleac!
$33.25 and up

Image Credit: Ruth Eckerd Hall

Tim McGraw
May 6
MIDFLORIDA Credit Union Amphitheatre
$29.50 and up

Tampa Riverfest

May 6-7
Curtis Hixon Park/Water Works Park
This two-day event along the Tampa Riverwalk is back for 2022! Enjoy two food-themed events – Taste of The Riverwalk and TacoFest – and rock out to a full concert series at Curtis Hixon park. Other events include a Wiener Dog Derby, Hot Air Balloon Glow, sidewalk chalk artists, and a stand-up paddleboard invasion.
Admission is free. Additional fee for food.

Image Credit: Tampa Riverwalk

Aerial Dragons
May 6-7
Straz Center
Aerial Dragons Studios invites you to a very important date! Join us for a journey down the rabbit hole for the revealing untold stories of Wonderland. Be dazzled by amazing aerial routines, daring dance numbers and fierce fire acts!
$73.13 and up

TJ Miller 
May 6-7
Tampa Improv
T.J. Miller has chosen Tampa to come and film his next comedy special, entitled “THE PHILOSOPHY CIRCUS”! Come to the Tampa Improv and be a part of history. A camera crew will be on site to shoot the entire special, including audience members and their reactions!
$64 and up

Maxwell: The Night Tour
May 7
Amalie Arena
Maxwell is touring in support of his new full-length album, blacksummers’NIGHT, out Spring 2022. Featuring Anthony Hamilton and Joe.
$70.25 and up

Things to Do in Tampa May 8-14

Florida Orchestra Pops in the Park
May 8
Julian B. Lane Riverfront Park
Enjoy the beautiful sound of music with The Florida Orchestra during this FREE Pops in the Park event in Tampa. Pack a picnic blanket and snacks and enjoy the music from hit films like Star Wars, Raiders of the Lost Ark, Broadway and MORE with mom under the stars with Daniel Black conducting.

Redwood Empire Whiskey Dinner
May 11
Ocean Hai
Come “Drink Among Giants” with Redwood Empire’s whiskey and bourbon selection. Join Ocean Hai and the Head Distiller Lauren, as she tells the story of the different selection of Redwood Empire whiskies, coming from the Russian River Valley in wine country, she will describe the unique sustainable way of their distilling process and the history of the company. Paired with a special Chef’s menu these whiskies are sure to delight your taste buds. Begins at 6pm.
$95 per person

The Bandwagon Tour
May 13
MIDFLORIDA Credit Union Amphitheatre
Miranda Lambert and Little Big Town are bringing The Bandwagon Tour back for round two! Featuring special guest, The Cadillac Three.
$24 and up

OCC Roadhouse & Museum Two-Day Southern Rock Concert Event
May 14-15
OCC Road House & Museum
This two-day event features live performances from popular southern rock and rock groups The Steel Woods (May 13) and Jackyl (May 14). Guests are encouraged to purchase individual VIP tickets and 6-seat VIP tables to guarantee seating. All VIP admissions include up-front viewing, dedicated restrooms, and dedicated bar and servers.
General Admission: $20/VIP: $50

Next Generation Ballet
May 14-15
Straz Center
Featuring NGB’s rising stars, this production promises to be all things that ballet is supposed to be – ravishing, exquisite, and powerful.
$20 and up

St. Pete Tacos & Tequila Festival
May 14
Vinoy Park
This waterfront festival will feature tons of authentic tacos, premium margaritas and great live music. Presented by Don Julio Tequila, this event will feature over 25 tacos vendors, great margaritas and other cocktail options, four great live bands, cold Coronas and Funky Buddha beer, games, prizes and so much fun!
$9 and up

John Mulaney “From Scratch” Tour
May 15
MIDFLORIDA Credit Union Amphitheatre
Former SNL writer and comedian John Mulaney brings his “From Scratch” tour to Tampa!|
$24 and up

Things to Do in Tampa May 15-21

Pretty Woman: The Musical
May 17 – 22
Straz Center
Pretty Woman: The Musical, based on one of Hollywood’s most beloved romantic stories of all time, is now on tour!
$41.50 and up

Halsey – Love and Power Tour
May 18
MIDFLORIDA Credit Union Amphitheatre
Best-selling artist Halsey returns to Tampa with special guests beabadoobee and Pink Pantheress.
$26.50 and up

Chris Kattan & Friends
May 18
Tampa Improv
Chris Kattan has created some of the most memorable characters in his 8 seasons on Saturday Night Live such as Mango, Mr. Peepers, Gollum, I Wish it Was Xmas Today!
$32 and up

Margarita Wars
May 19
Tampa River Center
This unique opportunity will allow you to sample margaritas created by more than a dozen of the Tampa Bay area’s best mixologists! Try your hand at tipsy judging as YOU help award Tampa Bay’s Ultimate Margarita! Plus, live entertainment, Mexican-inspired hors d’oeuvres, and other fun surprises.

Rob Schneider
May 20
Bilheimer Capitol Theatre Clearwater
Stand-up comic and veteran of the award-winning NBC sketch comedy series Saturday Night Live, Schneider has gone on to a successful career in films, television and continues his word-wide standup tour.

Bill Burr: Slight Return
May 20
MIDFLORIDA Credit Union Amphitheatre
Comedian Bill Burr (Chapelle’s Show) takes his latest comedy act on stage here in Tampa. *Please note: this is a cell-phone free event. Locked pouches to keep phones in will be provided and anyone caught using their phone to record will be removed from the event.
$54 and up

I’m Not a Comedian…I’m Lenny Bruce
May 20-22
Straz Center
This show draws from Bruce’s stand-up routines, writings and court records for an intimate portrait of the gifted, ground-breaking and ultimately doomed comic. For ages 18+ only.

Kane Brown: The Blessed & Free Tour
May 21
Amalie Arena
Featuring special guests Walker Hayes and Raelynn.

Things to Do in Tampa May 22-28

Jersey Boys
May 24-25
Ruth Eckerd Hall
The Behind-The-Scenes Tony-Award winning Broadway Musical about Frankie Valli & The Four Seasons returns!

Fourth Friday Tampa
May 27
Tampa Riverwalk
Fourth Friday Tampa is a monthly arts & culture crawl throughout Tampa’s Downtown, providing you an evening of special offerings, live music, programs by cultural destinations and much more!

Rule #7 Beer Release 
May 28
Crooked Thumb Brewery
Rule #7 Hurricane Pale Ale will be released on draft and in 4 packs of cans. Named for Denis Phillips, ABC Action News’s meteorologist who is always there to help us weather any storm. Denis will be there for the release, holding a meet & greet from 3-5pm.
Free (beer purchase separate)

Margarita & Music Fest
May 28
Julian B. Lane Riverfront Park
Enjoy live music, dozens of margaritas, games, shopping, great food options, and end the night with a bang with the largest fireworks show in the area. Lynyrd Skynyrd headlines supported by Elle King, and The Village People. 21+ only.

Things to Do in Tampa May 29-31

11th Annual Cuban Sandwich Festival
May 29
Centennial Park
Enjoy live cultural music on stage featuring live music and dance performances, a true cultural festival featuring food, art, and cultural exhibitors.

More Things to Do – Ongoing Tampa Bay Events

Busch Gardens Food & Wine Festival
March 11-May 22
Busch Gardens Tampa Bay
With more than 20 NEW delicious dishes to pair with wines, craft brews and cocktails, park guests can explore a variety of flavors while enjoying a diverse concert lineup, including acts for all tastes. Complete with signature cocktails like the Iron Gwazi Fizz or frozen watermelon margaritas, a selection of more than 40 wines and beers, this year’s menu offers an endless variety of flavors to sip and savor. The Food & Wine Festival runs Fridays through Sundays from March 11 to May 22 and is included with admission to the park.

Picasso and the Allure of the South
Through May 22, 2022
The Dalí Museum
Picasso and the Allure of the South, presented exclusively at The Dalí, explores the influence of southern Europe on Pablo Picasso’s revolutionary work.
Included with regular museum admission

Michaelangelo’s Sistine Chapel: The Exhibition
April 29-June 26

WestShore Plaza
This exhibit is reproduced using state-of-the-art technology and is suitable for all audiences, relying on a spacious area where Michelangelo’s masterpieces stretch floor-to-ceiling and closer than ever. The experience will awaken visitors’ curiosity by presenting a never-before-seen perspective of his timeless masterpieces.
$19.20 and up

Musical Bingo Night
Tuesdays from 8-10pm
Crafty Squirrel St. Pete
Two rounds of musical bingo with 8 prizes. Plus enjoy the weekly Taco Tuesday special: a la carte Americana style tacos are only $2!
FREE Admission

Fairgrounds St. Pete
Permanent exhibition open Thursdays-Sundays
800 28th St S, St. Petersburg, FL 33712
Fairgrounds St. Pete is a permanent indoor immersive, explorable art and technology experience in St. Pete, Florida. Over 60 local and international artists were commissioned to make art for you to immerse yourself in and enjoy.

Related: Choose-Your-Own-Adventure at Fairgrounds St. Pete

Art on the House
Thursdays from 4-8pm
Tampa Museum of Art
Every Thursday from 4 to 8 pm, the Tampa Museum of Art offers Art on the House where admission prices change to pay-as-you-will, and visitors choose whatever admission price they want to pay. Bring the family and celebrate 100 years of art in Tampa with exhibitions that emphasize ancient, modern, and contemporary art.
Choose your own admission price

St. Pete Shuffle Friday Nights
Fridays from 7-10pm
St. Pete Shuffle
Learn to play shuffleboard with help from St. Pete Shuffle’s staff and volunteers, who will get you set up on a court and teach you how to play.
$10; free for members and their guests

St. Pete Walking Mural Tours
Saturdays from 10-11:30am
Tour begins at Florida CraftArt, 501 Central Ave. in downtown St. Petersburg
Visitors will hear the inside stories of the making of over 30 murals found in the four block tour. Limited to 10 people, masks required, book prior to 4 p.m. the prior day.

Bend, Bubbles & Brunch
Sundays from 10-11am
Epicurean Hotel
Recenter and restart with poolside yoga. Keep the relaxation going with a complimentary glass of Champagne or Ketel One Botanicals cocktails at the end of class. Enjoy all day pool access and stay for brunch at Élevage.
$25 in advance; $30 at the door

Looking for more things to do this week?

Check out this guide to family-friendly events in Tampa Bay from our sister publication Tampa Bay Parenting Magazine. Heading to Orlando? Here’s a guide to the best Orlando events this month at the theme parks and beyond.


Featured image credit: Tampa Riverwalk


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