Browse by Feature

Walkway to the beach with blue water and sky
Search All Rentals

Your vacation home is waiting!

We have just the place for you.

Unveiling the Spring Charm: Annual Events in Destin, FL


Destin, FL, renowned for its pristine beaches, emerald green waters and is often dubbed the “World’s Luckiest Fishing Village,” is not just a summer paradise. As the warmer winds begin to tousle the palm trees, Spring ushers in a vibrant selection of events that cater to every visitor and local. Here’s a glimpse into some of the enchanting annual festivities that take place in March, April, and May.

Burning Up the Beaches (March)

Burning Up the Beaches is more than just a classic car show — it’s an exhilarating concoction of gleaming chrome, sun-soaked beachfronts, and heartwarming generosity. Whether you’re an ardent car enthusiast or a casual beach-lover, this event promises an experience worth experiencing and remembering.


The event sets wheels in motion with early packet pickup and on-site registration, where the automotive community begins to gather and ignite the start of an exciting weekend. Participants prepare for the activities to come, radiating nothing but anticipation and camaraderie.


As the festival revs up, participants delight in a full day of unique cruise stops, which they can explore at their leisure. The specifics of these stops are thoughtfully detailed in a driver’s handbook given to attendees.


As the sun begins to set, the festival shifts gears to the Beach Bash – a themed dinner party where guests can dine together, share stories and enjoy the live band’s riveting performances. It’s a night where laughter and music sound as great as the purr of a well-tuned engine.


The heart of the event unfolds at Destin Commons, aptly named ‘Car Show Central.’ Here, among the sheen of chrome and vibrant hues of retro paint jobs, the nostalgic magic unfolds, capturing the imaginative spirit of eras past. The event reaches its peak with a valve cover race and awards ceremony, with the entire affair set to a soundtrack provided by a local DJ.


So why wait? Start your engines and gear up for a memorable experience.

Paradise Music Festival (March)

Set your calendar for a melodious rendezvous at the Paradise Music Festival, a captivating musical event hosted in the heart of Florida’s Emerald Coast. Hosted at the sprawling Destin-Ft. Walton Beach Convention Center, the festival offers an enticing roster of auditory delights, curated from a myriad of genres and artistic styles. It’s a gathering that brings the musical virtuosos and fans together, painting a vibrant sonic landscape spanning across a full weekend.


From budding musicians setting their first chord on a public stage to well-established names sending waves through the industry, the Paradise Music Festival is an inclusive platform that celebrates the power of music. The festivities run from Friday through Sunday, with each day offering a unique blend of performances scheduled to perfect rhythm, ensuring there’s never a dull moment. The event is managed seamlessly under the adept guidance of Rik Wolfe, popularly recognized from 100.3 KROCK – Omni Broadcasting.


Centered within the beautiful Destin-Ft. Walton Beach Convention Center, the festival’s location sets the right tone, both in terms of ambiance and convenience. The center’s expansive space provides the perfect pitch for the festival’s energy, while the no outside food or drinks policy points to an array of culinary options available on-premises provided by Aramark services. Nestled along the sparkling Miracle Strip Parkway, it’s a remarkable setting for a musical rendezvous that resonates with exciting performances and an inviting environment that lasts long after the last note has played.

Sandestin Wine Festival (April)

Uncork the magic at the iconic Sandestin Wine Festival, where sun-kissed shores and opulent bouquets of fine wine converge in a symphony of taste and celebration. This prestigious event, hosted at the scenic Village of Baytowne Wharf within the Sandestin Golf and Beach Resort, is a time-honored tradition that boasts four days of exquisite wining and dining. Bringing together wine enthusiasts, foodies, and sunshine lovers, the festival offers an unrivaled opportunity to indulge in the rich diversity of wines from around the globe, all in the lap of coastal luxury.


Imagine strolling along the lush walkways of the resort, wine glass in hand, as you navigate through an impressive array of wine vendors, each eager to share the story behind their vintage. As the festival unfolds, connoisseurs can sip and savor different varietals, attend exclusive dinners like Roberto’s Santa Margherita Dinner, and spark their morning with a Farewell Brunch


As the dates draw near for the next Sandestin Wine Festival, mark your calendars for a rendezvous with luxury and leisure. Whether you’re looking to expand your wine palate or simply enjoy the carefree ambiance of Florida’s Gulf Coast, this festival promises elegance, education, and entertainment wrapped in one unforgettable weekend.

Fly Into Spring Kite Festival (April)

Kite Festival

As the clear blue skies of Fort Walton Beach meet the breezy, salt-tinged air, there’s an unparalleled kaleidoscope of colors that takes shape, thanks to the Fly into Spring Kite Festival. Hosted by Kitty Hawk Kites at The Boardwalk on Okaloosa Island, this annual event is a visual spectacle like no other. Envision the sky dotted with the likes of a 100-foot octopus, an 80-foot panda, and a 50-foot gator; these aren’t creatures of the deep or a child’s oversized stuffed animals, but rather kites—majestic in size and whimsical in nature, soaring high during this two-day event that mesmerizes onlookers, young and old.


Set against the backdrop of Fort Walton’s stunning coastline, the festival is more than a gathering; it’s an experience steeped in free-spirited fun and open to all ages. Join Kitty Hawk Kites and the Emerald Coast Kite Flyers Club in a shared passion for kite flying, with activities that are unparalleled in their family-friendly appeal. Whether you’re marveling at the professional stunt kite flying demonstrations, taking your first fly with free kite flying lessons, or simply enjoying the community vibe during the family fun fly, there’s an undeniable magic in the air. The event not only showcases remarkable show kites but also offers special activities inside the Kitty Hawk Kites store, making for an all-encompassing experience that harnesses the joy of wind-powered wonders.


Nestled at 1450 Miracle Strip Pkwy within the heart of Fort Walton Beach, FL, Kitty Hawk Kites is the go-to destination for all things airborne. This festival highlights their dedication not only to the craft of kite making but also to creating an environment where joy, education, and community engagement take flight.

Seabreeze Jazz Festival (April)

In the sun-drenched landscapes of Panama City Beach, FL, the Sea Breeze Jazz Festival has become a beacon for smooth jazz lovers across the nation. Held at the Aaron Beasant Park Amphitheater, a venue that boasts both the charm of scenic beauty and the convenience of modern facilities, the festival offers an immersive experience that goes beyond mere performances. Each year, 600 S Pier Park Dr. transforms into a vibrant congregation point for artists and enthusiasts alike, under the expansive Florida sky.


The festival, renowned for its eclectic lineup, showcases a who’s who of the jazz world. While the artists and performance times are subject to change, the unwavering quality of music and the palpable excitement in the air remain constants. Attendees are encouraged to keep an eye on the official schedule to catch their favorite performers in action. Beyond the soul-stirring concerts, the Sea Breeze Jazz Festival enhances the experience with its array of after-parties, jazz cruises, and the presence of festival-exclusive artists, making it a comprehensive celebration of the genre.

South Walton Beaches Wine and Food Festival (April)

Celebrating over a decade of distinctive gatherings, the SoWal Wine Festival has become a cherished tradition, much anticipated by wine enthusiasts and casual sippers alike. Nestled in the heart of South Walton, this festival stands out not only for its selection of fine wines but also for its commitment to bringing people together in a shared expression of philanthropy and appreciation for the finer things in life. Every year, the quaint yet vibrant communities of South Walton transform into a hub of oenophilic delight, offering attendees an opportunity to immerse themselves in a world of exquisite tastes, aromas, and experiences.


The festival, with its meticulous planning and thoughtful execution, promises an enriching four-day experience. It’s not merely an event; it’s a celebration of the rich tapestry of wine culture, underscored by the spirit of giving back to the community. Each sip not only offers a journey through diverse vineyards and boutique selections but also contributes to a greater cause, enhancing the significance of every glass raised. The SoWal Wine Festival is more than an event; it is a beacon for connoisseurs and novices alike, a place where stories are shared, memories are made, and the love of wine continues to flourish.


As the festival continues to evolve, the heart of its mission remains steadfast: to gather together under the bright Florida sun, to relish in the joy of discovery, and to toast to the future of charity and unity through the universal language of wine.

Memorial Day Weekend Celebrations (May)

As summer beckons with its promise of sunny days and clear night skies, there’s no place like HarborWalk Village in Destin, Florida, to kick things off. The Memorial Day Weekend Celebration at HarborWalk Village is an eagerly awaited event that marks the unofficial start of summer in spectacular fashion. The celebration transforms the Destin Harbor into a vibrant stage for live music, dazzling air shows, and mesmerizing fireworks, creating an atmosphere of pure joy and excitement for locals and visitors alike.


The festivities commence with an evening of live music where the lineup promises to enthrall attendees with powerful performances set against the scenic backdrop of Emerald Grande. The excitement continues with a respectful remembrances ceremony, accompanied by a vintage air show, inviting everyone to look skyward in awe. As the sun sets, the night sky lights up with fireworks and fire spinning, painting the harbor with vibrant colors and energy. The celebration doesn’t stop there; a Silent Disco on Captain’s Deck and live music ensure the party goes on, capped off with another brilliant fireworks and fire spinning display.


With an on-site parking fee that includes all-day access and same-day return, the Memorial Day Weekend Celebration at HarborWalk Village is both accessible and convenient, making it an unmissable event for those looking to commemorate the holiday in style. Set against the idyllic location of 10 Harbor Blvd, Destin, Florida, this annual event offers a perfect blend of entertainment, remembrance, and summer fun, welcoming the warmer months with open arms and uplifted spirits.

Digital Graffiti Festival (May)

In the heart of Alys Beach, where modern technology meets creativity, Digital Graffiti shines as a unique festival that captivates artists, tech enthusiasts, and visitors from around the world. This avant-garde event transforms the town’s stark white walls into a canvas of light, where immersive technology allows digital artworks to play across facades in a breathtaking display of color and movement. Evolving beyond traditional art forms, Digital Graffiti explores how design, technology, and architecture can intertwine to create new experiences that pulse with life and innovation.


Digital Graffiti not only serves as a platform to showcase groundbreaking digital art and interactive installations but also offers a sensory overload with a sophisticated culinary edge. Designed as an adult-only (21+) affair, the festival features an all-inclusive food and beverage experience, setting itself apart from any other art show. As you stroll through the path adorned with groundbreaking installations, you’re met with culinary creations from the finest local and regional chefs, alongside exquisite offerings from renowned winemakers, distilleries, and breweries. This evening at Digital Graffiti is a feast not only for the eyes but also for the palate, making it an annual spectacle that highlights the best of art, taste, and community spirit in a celebration unlike any other.

Stay with RealJoy

Choosing to stay with RealJoy for your next Florida getaway is the key to unlocking a vacation experience that perfectly blends the beauty of the Emerald Coast with the comfort and luxury of home. From stunning beachfront properties that offer a doorstep to the sands, to luxurious resorts that boast top-notch amenities and breathtaking Gulf views, RealJoy caters to every taste and budget. Our carefully curated portfolio of vacation rentals spans from Destin to Panama City Beach, including exclusive spots along the scenic 30A, ensuring that you find your dream vacation setting. 


RealJoy Vacations isn’t just about providing a place to stay; it’s about perfecting the family vacation. We understand that a trip to the Emerald Coast is an opportunity to create lifelong memories, which is why our accommodations are designed to enhance your vacation from the moment you arrive. Imagine waking up to the sound of waves at a beachfront home, or exploring the clear emerald waters of the Gulf from your beach view rental. With RealJoy, you also have the chance to bring your furry friends along to one of their pet-friendly properties, ensuring no member of the family is left behind. Our commitment to excellence and deep local knowledge promises not just a vacation, but an experience that will have you returning to the Emerald Coast time and again.

Explore more blogs