35+ Tampa Bay Events for Date Night: May 2021

Best of November: Our Guide to Date Night Events this Month


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. Highlights this month include a special after-hours soiree at The Dalí, an outdoor music fest celebrating Black heritage, nighttime art walks, u-pick sunflowers and so much more. Here’s our curated guide to the best Tampa Bay events for date night this May 2021.

PS: Check back often as we add more Tampa Bay events to this listing throughout the month.

MAY 1 – 9

St. Pete Mural Tour by Bike
Saturday, May 1, 9am
Tour departs near Florida CraftArt
Hop on your bike or take advantage of Coast Bike Share for a leisurely ride with numerous stops. Learn more about these dynamic murals and the power of public art in St. Pete! Bike rental included.

Cinco De Mayo Celebration
Wednesday, May 5, 4pm
Armature Works
Enjoy live traditional Mexican music from 6-8pm by Mariachi Internacional Tapatio, as well as a pop-up bar on the lawn featuring Don Julio Frozen Margaritas and various food and drink specials from the HPM vendors.
FREE Admission

Juan Gil Winery + Hotel Haya Outdoor Wine Dinner
Thursday, May 6, 6-9pm
Hotel Haya
Join Juan Gil Winery for an outdoor dinner at Hotel Haya prepared by Executive Chef Douglas Rodriguez. Influenced by the fresh, bold flavors of Spain, each course will be thoughtfully paired with pours from Juan Gil Family Estates in Jumilla, Spain.

Downtown Concert at Rock The Park
Thursday, May 6, 7pm
Curtis Hixon Waterfront Park
Rock the Park returns to Curtis Hixon Waterfront Park starting April 1, 2021. This month’s free outdoor concert features performances from Fantastical Tigers, BadCameo, and Deb Ruby.
FREE admission

Tampa Bay events
Image credit: Rock The Park Tampa

Gulfport First Friday Art Walk
Friday, May 7, 5-9pm
Downtown Gulfport
Making its debut as the premiere art walk in Pinellas County in 1993, Gulfport’s First Friday Art Walk welcomes the region’s most innovative artists for a showcase of creativity and community among the vibrant restaurants and storefronts along scenic Beach Boulevard.
FREE Admission

Springtime Sidewalk Social
Saturday, May 8, 10am-9pm
Book + Bottle
Peruse boutiques at the 500 Block including Book + Bottle, z.aa, and Twig, plus enjoy live music, flowers and charcuterie boxes for purchase.
FREE Admission

Plant Parenting with Yura Vina Bros
Saturday, May 8, 1-2pm
Epicurean Hotel
This hands-on experience will allow you to pot a new plant to take home and call your very own. Tickets include one glass of champagne and one plant kit (6 in calathea plant, planter and soil).

21st Annual Tampa Bay Black Heritage Festival Music Fest
May 8 – 9
Curtis Hixon Waterfront Park
A cultural event that features speakers, musicians, artists, poets, craftspeople locally and nationally.
Tickets start at $20/couple

Next Generation Ballet’s Swan Lake
May 8 – 9
Straz Center
This glorious story ballet follows beautiful Odette, trapped in a swan’s body by an evil sorcerer’s spell. Only Prince Siegfried’s love can break the curse – but when the sorcerer tricks Siegfried into proclaiming his love for the wrong woman, Odette must risk her life to change her fate.

Second Sunday Art Walk + Vendor Fair
Sunday, May 9, 11am – 3pm
Armature Works
Features a rotating cast of artisanal artists and makers selling handmade goods, jewelry, art, wood-work, gifts plus so much more in the Gathering space at Armature Works.
FREE Admission

MAY 10 – 16

Charcuterie Workshop with Gather ‘Round & Graze
Tuesday, May 11, 7-8pm
Book + Bottle
In this workshop, learn how to choose domestic and imported cheese and charcuteries for your board, how to arrange an array of exciting accoutrements, and how to put it all together. All materials provided. Tickets also include a glass of wine.

Gather 'Round & Graze workshop - Tampa Bay Events May 2021
Image credit: Gather ‘Round & Graze

Heights Night Market
Wednesday, May 12, 5:30-9:30pm
Armature Works
Monthly outdoor market featuring live music plus a rotating cast of artisanal artists and makers selling handmade goods, jewelry, art, wood-work, gifts and so much more. Family friendly.
FREE Admission

Havana Nights Under the Stars
Friday, May 14, 7-10pm
Safety Harbor Resort and Spa
Enjoy the sounds of live Latin music with Tropical Rhythms and dance the night away on the waterfront promenade! Tickets include appetizers, a Cuban dinner buffet, welcome cocktail and live music. Handcrafted cocktails, beer and wine available at cash bar.

TTRL’s Riverwalk & Chill
Friday, May 14, 7pm
Straz Center for the Performing Arts
Join Roxanne Gallo and Zachary Hines as they showcase local and regional singers for a concert along the Hillsborough River featuring St. Pete singer/songwriter Mountain Holler, Lakeland’s Noan Partly putting a jazzy twist on indie-folk and longtime Tampa-area performer J’Nelle with her pop and R&B sensibilities combined with the flavor of the Caribbean.

St. Pete French Fry Fest
Saturday, May 15, 3-10pm
Albert Whitted Park
Enjoy this 5th annual festival complete with food trucks, live music and craft beer.
FREE Admission

Gulfport’s Third Saturday IndieFaire Night Market
Saturday, May 15, 5-9pm
Downtown Gulfport
Night market brimming with art, jewelry, plants, crafts, and other locally crafted finds.
FREE Admission

A Night at the Brewseum
Saturday, May 15, 6-10pm
3 Daughters Brewing
Play like a kid and drink like a local while supporting local nonprofit Great Explorations Children’s Museum! Adults will enjoy a lively evening of craft beer tastings, EX Games competition, live music, opportunity drawings, and more.

Eric Schwartz LIVE at Tampa Improv
Sunday, May 16, 7pm
Tampa Improv
Hot off of Jo Koy’s Just Kidding World Tour, Eric Schwartz returns to the Tampa Improv for one night only! Eric Schwartz is a multi-dimensional showman who combines stand-up, music and visual elements to entertain audiences from all angles.

MAY 17 – 23

Couples Cooking: Stuffed
Tuesday, May 18, 6pm
Publix Aprons Cooking School – Tampa
Learn to make a variety of stuffed dishes during this hands-on cooking class. Menu includes Chicken Cordon Bleu with Dijon Horseradish Sauce, Crab-Stuffed Seasonal White Fish with Beurre Blanc, Spicy Sausage & Rice Stuffed Pepper with Pepper-Jack Cheese and Cream Puffs with Hazelnut Crème.

Sips & Sights: An Evening of Fine Art and Wine Pairing
Thursday, May 20, 6-8pm
Armature Works
Sips & Sights will take a look at wine as a form of art, and invite you to do the same in this dynamic event where 5 special pieces from Stella Gallerie will be shown, discussed, and then paired with a unique wine that speaks to the style of the piece or artist.

3rd Thursday Tampa
Thursday, May 20, 6-10pm
Grand Central at Kennedy
Downtown Tampa’s monthly street food fest. Free 2-hour parking and dog-friendly.
FREE Admission

Tampa Bay events - 3rd Thursday Tampa
Image credit: 3rd Thursday Tampa

Arts Legacy REMIX: Jazz, Jazz, Jazz
Friday, May 21, 7:30-9pm
Straz Riverwalk
Celebrate Jazz, America’s greatest contribution to the musical landscape, with an emphasis on the big band sounds of Afro Latin Jazz.

Fitness in the Wild: Yoga with Bella Prana
Saturday, May 22, 8:30-10am
Pose like your favorite animal in a yoga class led by an instructor from Bella Prana Yoga & Meditation. Yogis of all levels can enjoy this wild event. Plus, enjoy an up-close animal experience before you work out.
$20; must be a ZooTampa member

Coffee Connoisseur
Saturday, May 22, 10am-12pm
Epicurean Hotel
Explore a tasting flight of 8 different coffees from the rare to the exotic. This entertaining class includes a live coffee roasting demonstration, unlimited coffee, two patisseries per guest and more.

The 5th Annual Incredible Duck Race
Saturday, May 22, noon
*VIRTUAL event
Adopt a Duck to help a child and you could be the Lucky Duck to win the $5,000 prize. The 5th Annual Incredible Duck Race is going VIRTUAL! Adopt a Duck for $5 at TampaDuckRace.com. First place prize is $5,000 and all proceeds benefit the Kiwanis Club of Tampa and helps kids in the local community. Winners will be announced on Facebook Live May 22 at 12pm.

2021 Florida Hard Seltzer Fest
Saturday, May 22, 1-6pm
3 Daughters Brewing
Try 3 Daughters Brewing’s brand new line of seltzers while enjoying live music, games, giveaways and food specials.
FREE admission

Saturday, May 22, 3-7pm
Bayshore Boulevard
From Swann to Bay to Bay Blvd., enjoy an afternoon of free-wheeling along the water with friends and family. So come dressed in your hippie best! Ticketed VIP event at Tampa Garden Club to follow the ride.
FREE (RSVP encouraged); VIP party $100-$150

Roman Renaissance: Street Food
Saturday, May 22, 4-6pm
Epicurean Hotel
Roman street food is much more than pizza. In this seminar, Chef Greg Baker will lead you through the essential pillars of Roman street food, with a modern spin, taking you out of the theatre and onto the streets of Rome.

Pride Celebration
Sunday, May 23, 1:30-9pm
Sparkman Wharf
In honor of the Official Tampa Pride Parade, celebrate Tampa’s LGBTQ + community with a day full of Pride-spirited activities! Enjoy a line-up of music, Pride Ride spin classes with Union Three Studio, fundraisers for Tampa Pride, and insta-worthy photo ops.
FREE Admission

A Starry Night at the Dalí
Sunday, May 23, 7-10pm
The Dali
Enjoy exclusive after-hours access to the Van Gogh Alive special exhibition, tarot card readings, music and a complimentary Van Gogh Vodka craft cocktail. Light fare from Café Gala will be available for purchase.

MAY 24 – 31

Movie on the Lawn – The Sandlot
Monday, May 24, 8:15-10pm
Armature Works
Families and friends of all ages are welcome to bring lawn chairs and blankets to enjoy this free outdoor showing. Enjoy food and drinks from any of the vendors with in Heights Public Market.

Image credit: Armature Works

Couples Cooking: Great Seafood at Home
Wednesday, May 26, 6pm
Publix Aprons Cooking School – Tampa
Creating great seafood dishes at home is easier than you think. Learn how while making a four-course meal during this hands-on cooking class.

Super Flower Moon Concert
Wednesday, May 26, 6-9pm
Fenway Hotel
Celebrate the Flower Moon with a concert by Reinhardt/George Band on your private tarp on the lawn! Bring your own chairs/blankets. Admission includes tickets for food and beverage stations

May Book Club: Never Let Me Go
Thursday, May 27, 6:30
Book + Bottle
This monthly book club features an in person discussion on the last Thursday of the month. May’s book is Never Let Me Go by Kazuo Ishiguro. Enjoy happy hour pricing from 4-6pm and waived corkage fees.
FREE Admission

Busch Gardens Summer Nights
May 28 – September 6
Busch Gardens Tampa Bay
Feel the spark after dark with fireworks, thrill rides and more.

Photo Credit: Busch Gardens

Sunset Music Festival
May 29 – 30
Raymond James Stadium
Sunset Music Festival is a celebration of life through creativity and musical conversation. Here you’ll find the finest and fittest DJs and performers, curated to perfection across five stages.

Goat Yoga Tampa
Sunday, May 30, 10:30am
In the Loop Brewing, Land O Lakes
Goats, yoga and beer (or wine)! Your ticket includes a free drink. Bring your own mat and towel.


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

Community Tchin-Tchin (Complimentary Wine Tasting)
Fridays from 5-7pm
Book + Bottle
Check out this casual Friday tasting at St. Pete’s local bookstore and wine shop. Themes change weekly.

Sunflower U-Pick
Saturdays and Sundays in May, 10am-3pm
HarvestMoon Fun Farm
Pick flowers through maze-like paths and bring home a beautiful bouquet for yourself our loved one! Cash only.
$10 minimum flower purchase

Tampa Bay events - Sunflower u-pick
Image credit: HarvestMoon Fun Farm

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.

Local Loop Saturdays
Saturdays from 12-6pm
Brew Bus Brewing
Local Loop is a Hop On Hop Off bus tour with set itineraries visiting some of Tampa Bays best craft breweries and destinations. Now with two days worth of itineraries riders can visit 8 craft breweries and destinations between Saturday and Sunday.

Van Gogh Alive
Extended through June 13
The Dalí Museum
Experience Vincent van Gogh’s works in an immersive art installation that opens a new window into the celebrated painter’s artistic genius. This must-see Tampa Bay event features more than 3,000 Van Gogh images at enormous scale, viewed through high-definition projectors and synchronized to a powerful classical score. Read more about this exhibit here.
Included with museum admission; timed entry tickets required

van gogh alive sunflowers
Van Gogh Alive

Check out our events page for even more Tampa Bay events.


Looking for fun things to do just a short drive away? Check out this full May event guide created by our sister publication, Orlando Date Night Guide. Here are a few highlights to consider:

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

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

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

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

Party from your Balcony at Orlando World Center Marriott Vertical Concert Series

Feature image credit: The Dali


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