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2025 Tampa Bay Winter and Spring Events

Kid on parents shoulder at Tampa Bay live music events

There’s always something happening in the Tampa Bay Area. Make the most of your Plumlee Gulf Beach Realty vacation and plan your trip around one of the annual events in the Tampa Bay Area. From Tampa’s historic Gasparilla Pirate Festival to Clearwater Beach’s renowned Sugar Sand Festival, there’s something to captivate every interest. Find the perfect basecamp in Indian Rocks Beach, and stay within easy reach of events throughout the region!

January 16-19: St. Pete Power & Sailboat Show

Join us for the largest boat show on the Gulf Coast this winter, The St. Pete Power & Sailboat Show. Head to St. Petersburg’s downtown waterfront, walk past hundreds of powerboats and sailboats, attend seminars, and sign up for fishing clinics. 

January 18: Children’s Gasparilla

Take the family to Children’s Gasparilla the weekend before the larger Gasparilla Pirate Festival. Find a spot along Bay Blvd. and watch the Children’s Gasparilla Parade, followed by a firework extravaganza. 

January 25: Gasparilla Pirate Festival

Experience Tampa’s longest-running festival, The Gasparilla Pirate Festival, celebrating the history and legacy of the famous pirate Jose Gaspar. Watch as pirates invade the city of Tampa, reclaim the key from the mayor, and celebrate their victory with a parade downtown. Head to Curtis Hixon Waterfront Park for live music throughout the day!

February 8-9: St. Petersburg Fine Art Festival

Find a unique piece of artwork to take home with you during the St. Petersburg Fine Art Festival. This two-day event at South Straub Park will feature over 100 artisans selling paintings, photographs, sculptures, metalwork, jewelry, ceramics, and more. 

February 15: Winterfest on the Rocks

Join Winterfest on the Rocks in Indian Rocks Beach, a lively neighborhood celebration offering family-friendly activities, arts and crafts vendors, live entertainment, and delicious food.

February 27-March 9: Florida Strawberry Festival

Head to Plant City for the Florida Strawberry Festival and celebrate all things strawberry this spring! Enjoy delicious strawberry treats, enjoy amusement park rides, catch world-famous entertainers, and learn about local agriculture. 

February 28 – March 2: Firestone Grand Prix of St. Petersburg

Every year, race fans converge in downtown St. Petersburg for the annual Firestone Grand Prix, part of North America’s top open-wheel racing series. Join the spectators and watch some of the fastest cars on the planet compete for the winning title.

March 17-23, Valspar Championship

Watch top PGA professionals compete during the annual Valspar Championship held at Innisbrook Resort. In addition to the tournament, you can expect food and drink vendors and related events like live music and contests.

March 28: John’s Pass Seafood Festival

If you are a seafood lover, John’s Pass Seafood Festival in Madeira Beach is not to be missed. Feast on fresh local seafood dishes from local vendors as you browse the arts and crafts booths and listen to live music. 

April 11-27: Pier 60 Sugar Sand Festival

Visit Clearwater Beach for the Pier 60 Sugar Sand Festival and watch professional sand sculptors transform the sugar sand into beautiful sculptures. In addition to the sculptures, you can expect free sand sculpting classes, live music, fireworks, artisans, and food vendors. 

Book Your Condo Rental in the Tampa Bay Area

Book your getaway with Plumlee Gulf Beach Realty and stay close to Tampa Bay events this winter and spring. Browse our condo rentals in Indian Rocks Beach and Indian Shores and find the perfect lodging for your group. Complement your vacation with our Plumlee Perks and enjoy amenities like free bike rentals, DVD rentals, and overflow parking. Check out our specials and save on your 2025 vacation in Indian Rocks Beach!