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Where to Play in May · Featured Events From 30A to Navarre Beach

Photo courtesy of Digital Graffit at Alys Beach

May brings a variety of fun events to the Emerald Coast with a charity wine dinner, two paddleboard races, a car show, a pirate invasion, two arts festivals, and even a festival celebrating tequila and tacos! In addition to featured events, many communities such as Seaside, Alys Beach, and Rosemary Beach will be hosting weekly concerts, plays, and movies in honor of spring. Scroll below for more info on our featured events!


Pairing and Sharing Wine Dinner
Rosemary Beach Town Hall | Rosemary Beach
May 4th, 2023

Sip, savor, and share a glass among friends while supporting a worthy cause. The inaugural wine dinner, Pairing and Sharing, to benefit Caring & Sharing of South Walton, will kick off with a cocktail hour with passed hors d’oeuvres followed by a 3-course dinner by Swiftly Catering paired with five wines from Dry Farm Wines.

Burning Up the Beaches Car Show
Destin Commons | Destin
May 4th – 6th, 2023

Gearheads get your motors runnin’! Burning Up The Beaches car show returns to Destin Commons with music and motors throughout the day and the Valve Cover Race at 11:00 AM. Burning Up The Beaches is a 3-day event with parties each day along the beautiful Emerald Coast! Participants who register for Show & Cruise get full access to all activities and parties.

Paddle at the Park
The Boardwalk | Okaloosa Island
May 6th, 2023

The 11th Annual Paddle at the Park Sponsored by HCA Florida Destin Emergency is a standup paddle board race that will take place in the Gulf of Mexico behind The Boardwalk on Okaloosa Island. It features 1- and 3-mile recreational races, a 6-mile elite race, and a kids’ fun out-and-back paddle, to be followed by awards. Kayaks and inflatables are welcome too.

Tequila and Taco Festival
Baytowne Wharf | Sandestin Golf and Beach Resort
May 12th – 13th, 2023

Hosted at The Village of Baytowne Wharf, local restaurants and food trucks compete for the Best Taco on The Emerald Coast with a first-place prize of $2,500. Festival guests get to cast their votes in the People’s Choice Award. Sample many types of Tequilas and Margaritas from Blancos, Resposados, Anjieos, and even Mezcals while indulging on some of the area’s best tacos.

35th Annual ArtsQuest Fine Arts Festival
Grand Boulevard Town Center | Sandestin Golf and Beach Resort
May 13th – 14th, 2023

Produced by the Cultural Arts Alliance of Walton County and presented by Grand Boulevard Town Center, ArtsQuest provides an opportunity to view and purchase original art from over 100 artists from around the country. The rain or shine event also features live performances, artist demonstrations, ImagiNation: where kids rule, food, beverages, and more!

Billy Bowlegs Pirate Festival
The Landing | Fort Walton Beach
May 13th – 14th, 2023

Ahoy Matey! The beloved Billy Bowlegs Pirate Festival returns to Fort Walton Beach with four days of festivities. On Thursday the Pre-Invasion features a Pub Crowl Downtown. The Skirmish on Friday includes a concert by the Unfortunate Sons followed by fireworks. The Invasion on Saturday includes live entertainment, vendors, bounce house, the pirates’ landing, and fireworks followed by the finale on Monday with the Torchlight parade.

Digital Graffiti
Alys Beach
May 19th—20th, 2023

Digital Graffiti at Alys Beach is a one-of-a-kind projection art festival with two days of exciting events. Kick off the weekend at the celebratory pre-party announcing the award-winning artists. On opening night, enjoy an adult-only, all-inclusive food and beverage experience that is a spectacle for the senses! For the finale, families and guests of all ages can experience the projection art installed along the festival path.

2nd Annual Navarre Paddle Classic
Navarre Beach Marine Park | Navarre Beach
May 20th, 2023

The 2nd Annual Navarre Paddle Classic Sponsored by Navarre Beach Yoga Studio will be held at the Navarre Beach Marine Park on the Santa Rosa Sound to benefit the Navarre Beach Sea Turtle Conservation Center. The event includes a, 12 Mile Race, 6 Mile Race, 6 Mile Technical Race, 3 Mile Technical Race, 1 Mile fun race, and a Kid’s race.

Memorial Day Celebration
Baytowne Wharf | Sandestin Golf and Beach Resort
May 27th – May 28th, 2023

Kick off your summer during our Memorial Day Celebration at The Village of Baytowne Wharf. Enjoy LIVE music all weekend! Plus on Sunday enjoy activities for the kids and a fireworks show at 9:00pm! Musical lineup includes the Forrest Williams Band on Saturday and the Trest Richerson Band on Sunday.

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