From insights into St. Pete Beach nightlife to top events in Madeira Beach FL and the barrier islands, here's a seasonal guide to festivals, concerts, art shows, and celebrations across the region.
Events in Madeira Beach FL, St Pete Beach Nightlife & Much More
From reggae on the waterfront to sand sculptures the size of small houses, the stretch from St. Pete Beach up through Treasure Island, Madeira Beach, the Redingtons, Indian Shores, and Indian Rocks Beach is basically one giant year-round celebration.
The vibe? Equal parts sunshine, creativity, and "why not make this a festival?"
At Resort Rentals, we offer a wide range of vacation homes featuring amenities like private pools, fully equipped kitchens, beachfront views, and pet-friendly options. As local experts, we also invite you to explore our destination blog. From rainy-day activities to the best breakfast in town, you'll find plenty of insider tips to make the most of your visit.
If you like planning trips around local happenings — or you just love knowing what's going on while you're here — consider this your seasonal cheat sheet.
Here's a little preview of what's ahead.
- Firestone Grand Prix of St. Petersburg (March): A High-Speed Street Race With Waterfront Views
- Reggae Rise Up (March): A Sunshine-Soaked Weekend of Reggae by the Water
- Tampa Bay Blues Festival (April): Soulful Music in a Picture-Perfect Park
- Pier 60 Sugar Sand Festival (April): A Giant World of Sculptures Made Entirely of Sand
- St. Pete Pride (June): Florida's Largest Pride Celebration
- Tampa Bay Ice Cream Festival (July): A Waterfront Celebration of Ice Cream (Yes, Really)
- Sunsets at Pier 60 (Every Evening): A Daily Festival for the Sun's Grand Exit
- SHINE St. Pete Mural Festival (October): Ten Days of Citywide Creativity
- Clearwater Jazz Holiday (October): Jazz, Sunshine, and Soft Lawn Blankets
- Sanding Ovations, Treasure Island (November): World-Class Sand Sculptures on the Beach
- Localtopia, St. Pete (February): A Giant Celebration of Local Makers and Creatives
- Holiday Boat Parades, Madeira Beach & the Islands (December): Sparkling Boats Lighting Up the Winter Nights
- St. Petersburg Fine Art Festival (February): A Winter Weekend of Art in the Sunshine
SPRING EVENTS & FESTIVALS
Spring here is the local secret weapon: warm but breezy, sunny but not face-melting, and packed with events that bring everyone outdoors.
1. Firestone Grand Prix of St. Petersburg, March
A High-Speed Street Race With Waterfront Views
The Firestone Grand Prix turns downtown St. Pete into a full-blown racecourse, complete with barriers, fast turns, and cars that blur into streaks of color. Even if you're not a motorsports devotee, the energy of the event — and its location along the water — makes it pure excitement from start to finish.
People love this event because the whole city buzzes with activity. The waterfront setting is spectacular, the weather is perfect for spending the day outside, and there's a festival-like atmosphere with food tents, music, and crowds cheering from every corner.
Families fit right in. Kids tend to be mesmerized by the speed, the noise, and the spectacle, making it a great outing even if they don't yet know the difference between IndyCar and go-karts.
2. Reggae Rise Up, March
A Sunshine-Soaked Weekend of Reggae by the Water
Reggae Rise Up transforms Vinoy Park into a three-day waterfront celebration of reggae, sunshine, and relaxed Gulf Coast vibes. Thousands gather on the lawn while big-name artists take the stage, and the ocean breeze does its part to keep things perfectly chill.
What keeps people coming back is the atmosphere: warm weather, joyful crowds, incredible music, great food, and a setting that feels tailor-made for a March festival. Even those who swear they "don't dance" usually end up swaying along.
It's family-friendly in a broad sense, best suited for teens and adults who enjoy live music and sunny afternoons stretched out on festival blankets.
3. Tampa Bay Blues Festival, April
Soulful Music in a Picture-Perfect Park
Also held at Vinoy Park, the Tampa Bay Blues Festival brings national blues talent to one of the most scenic spots in St. Petersburg. The stage overlooks the water, and rows of food vendors, and people lounge under the sun while guitar solos ripple through the air.
People adore this event for its atmosphere. The combination of mellow blues, blue skies, and blue waters feels almost poetic. The festival is large enough to feel lively but intimate enough that you can always find a quiet patch of grass.
Families with older kids, especially those who enjoy live music, will have a great time. Younger children tend to prefer shorter visits, but the open lawn layout makes it easy to roam.
4. Pier 60 Sugar Sand Festival, April
A Giant World of Sculptures Made Entirely of Sand
The Pier 60 Sugar Sand Festival turns Clearwater Beach into a temporary wonderland of enormous, intricately carved sand sculptures. Inside a massive tent, you'll wander through scenes and structures sculpted by artists from around the world, all made from pure, powdery Gulf sand.
Visitors love the creativity and scale of the sculptures, plus the accompanying live music, fireworks, and entertainers that pop up throughout the festival grounds. It's the kind of event where you stroll in expecting a nice hour or two and end up staying until sunset.
As you can imagine, it's extremely family-friendly. Kids adore the sculptures and performers, and adults appreciate the built-in "beach day + event" combination.
SUMMER EVENTS & FESTIVALS
Summer here is bright, busy, colorful, and wonderfully chaotic in the best beach-town way. Think Pride parades, ice-cream celebrations, and nights that run long on purpose.
5. St. Pete Pride, June
Florida's Largest Pride Celebration
St. Pete Pride is a month-long celebration of love, identity, and community and the biggest Pride event in Florida. Parades, concerts, street fairs, art installations, and waterfront gatherings take over the city, drawing over 100,000 visitors.
People love St. Pete Pride because it's joyful, inclusive, creative, and packed with energy. Every week brings something new, from family-friendly festivals to glamorous nighttime celebrations — and the spirit of the month is nothing short of contagious.
Many daytime events are fully family-friendly, with designated zones for crafts, performances, and activities for younger attendees.
If you want a fuller sense of what the event is all about, take a look at this recent write-up we've worked on. It breaks down the major moments and highlights from the month-long celebration.
6. Tampa Bay Ice Cream Festival, July
A Waterfront Celebration of Ice Cream (Yes, Really)
If you didn't know, National Ice Cream Day is a thing, the St. Pete Pier will happily remind you. The Tampa Bay Ice Cream Festival brings dozens of local ice-cream makers together for a sun-filled, sugar-forward waterfront celebration.
Visitors love wandering from booth to booth tasting flavors you won't find anywhere else. Add live music, happy crowds, and the sparkling bay as your backdrop, and it becomes summer distilled into an afternoon.
It's extremely family-friendly, of course — just be prepared to negotiate with children who absolutely need a second (and third) cone.
7. Sunsets at Pier 60, Every Evening
A Daily Festival for the Sun's Grand Exit
Every night of the year, Clearwater Beach hosts a sunset festival at Pier 60. Think live performers, local artisans, street musicians, and a warm crowd gathering to watch the Gulf sky turn into gold and cotton candy.
People love this tradition because it feels spontaneous and magical, even though it's scheduled. The entertainment rotates, the vendors change, and the sunset never repeats itself. It's one of the most iconic things to do in the area.
Completely family-friendly. Kids adore the magicians, dancers, and fire performers.
FALL FESTIVALS & EVENTS
Fall brings the best weather of the year — warm days, cooler evenings — and a calendar absolutely packed with culture, art, music, and sand sculptures.
8. SHINE St. Pete Mural Festival, October
Ten Days of Citywide Creativity
The SHINE Mural Festival brings local, national, and international artists together to transform St. Pete's buildings into vibrant murals. For ten days, the city becomes an open-air gallery of color, character, and unexpected beauty.
People love it because there's art around every corner, and watching new pieces come alive in real time is surprisingly moving. Guided walks, bike tours, and special events keep things lively.
It's a wonderful outing for families. Kids love hopping from mural to mural, and who knows — maybe one of them will reveal they're an artist in the making?
9. Clearwater Jazz Holiday, October
Jazz, Sunshine, and Soft Lawn Blankets
Clearwater Jazz Holiday is one of the region's most beloved traditions. It brings a wide range of artists — jazz, swing, blues, folk, Americana, and funk — to a festival that feels both polished and laid-back.
People come for the music, but they stay for the mood: ocean breezes, picnic blankets, and mellow late-October sunshine. It's a highlight of the fall for locals and visitors alike.
Families will find it relaxed and welcoming, especially for daytime sets.
10. Sanding Ovations (Treasure Island), November
World-Class Sand Sculptures on the Beach
Sanding Ovations turns Treasure Island into a sand-sculpting arena where professional artists create elaborate works that seem too perfect to be temporary. The event spans two weekends and includes music, vendors, and fireworks.
Visitors love the combination of art and beach. Where else can you marvel at a 15-foot sand sculpture, grab a drink, and then walk straight into the Gulf? The atmosphere is cheerful, playful, and endlessly creative.
It's very family-friendly. Kids love the sculptures, and adults appreciate the beachside festival vibe.
WINTER EVENTS & FESTIVALS
Winter here is something special. While the rest of the country bundles up, the Gulf Coast shines with lights, art festivals, boat parades, and perfectly mild beach days.
11. Localtopia (St. Pete), February
A Giant Celebration of Local Makers and Creatives
Localtopia is one of St. Pete's signature events, a massive community celebration showcasing local makers, artists, food trucks, and small businesses. You'll wander for hours, discovering everything from handmade ceramics to gourmet snacks.
People love it because it's peak St. Pete: creative, bright, community-driven, and filled with surprises. It's the best single-day snapshot of the city's personality.
It's totally family-friendly, with plenty of open space and activities for kids.
12. Holiday Boat Parades (Madeira Beach & the Islands), December
Sparkling Boats Lighting Up the Winter Nights
Holiday boat parades glide through the waterways of Madeira Beach, Treasure Island, and the neighboring islands, making them some of the most beloved events in Madeira Beach FL. Dozens of glowing boats drift along the shore while crowds gather to cheer them on.
People adore these parades because they're festive, charming, and uniquely coastal. Lights bounce off the water, kids shout with excitement, and the entire shoreline feels wrapped in holiday spirit.
It's wonderfully family-friendly, bring hot chocolate and warm clothes for the breezy night air.
13. St. Petersburg Fine Art Festival, February
A Winter Weekend of Art in the Sunshine
Held downtown, the St. Petersburg Fine Art Festival showcases artists from across Florida and the U.S. in a beautiful waterfront setting. Expect everything from sculpture and painting to jewelry, glasswork, and ceramics.
Visitors love it because it combines perfect winter weather with high-quality art and a walkable, scenic venue. It's cultural, but in that low-key Florida way where no one judges you for arriving in flip-flops.
Families enjoy strolling through the booths, and older kids often love picking out a memorable piece to take home.
COME FOR THE FESTIVALS, STAY FOR THE BEACHES
Each part of this coastline brings something different to the table.
Madeira Beach is known for its festive spirit and beloved local celebrations, especially the glittering holiday boat parade, one of the top events in Madeira Beach FL every year.
Treasure Island delivers mellow charm and postcard sunsets. Indian Shores and Indian Rocks Beach offer peaceful mornings and family-friendly days.
But when the sun goes down? St. Pete Beach wakes up. The area's rooftop bars, live-music venues, and open-late lounges give St Pete Beach nightlife its well-deserved reputation for being lively, colorful, and effortlessly fun.
Wondering Where to Stay During Your Trip?
Pick from Resort Rentals' great selection!
At Resort Rentals, we offer wonderful vacation homes with pools, BBQ areas, and more, allowing you to enjoy the beachy vibes with the whole family without spending much extra.
A beautiful coastal escape is waiting for you.
