Exciting Annual Pirate Festivals in Florida You Should Attend

Florida’s pirate history runs deep — from legendary buccaneers to hidden coves and coastal battles, the Sunshine State has long been a playground for pirate lore. Today, that legacy lives on through vibrant pirate festivals, themed parades, and family‑friendly celebrations held throughout the year.

If you’re ready to embrace the pirate life, unwind, and enjoy unforgettable adventures with your crew, these annual pirate festivals are the perfect place to start. Many are ideal for families, so bring the kids and let them experience the magic of Florida’s swashbuckling spirit.

Here are some of the top 2026 pirate festivals in Florida you won’t want to miss.

 🏴‍☠️ Gasparilla Pirate Festival – Tampa

📅 January 31, 2026
📍 Tampa, Florida
🔗 Official Site: gasparillapiratefest.com

The iconic Gasparilla Pirate Festival has been a Tampa tradition since 1904. It includes a large pirate parade and an array of related community events. Each year, the legendary pirate ship José Gasparilla II sails into downtown Tampa with a massive flotilla, demanding the key to the city from the mayor.

Upon reaching their destination, the invading pirates will raise the flags, mark their territory, and take the Gasparilla celebration on land. The festivities continue with one of the largest parades in the country, complete with elaborate floats, costumed pirates, live music, and endless entertainment.

Dress in your best pirate gear, enjoy delicious food and drinks, and join the revelry as Tampa surrenders to the buccaneers.

🏴‍☠️ Children's Gasparilla Parade– Tampa

📅 Saturday, January 24, 2026 - 12:00 P.M. – 7:30 P.M.
📍 Tampa, Florida
🔗 Official Site: Gasparilla Children's Main                                                      

The Children’s Gasparilla Parade is one of the community events leading up to the Gasparilla Day Pirate Invasion. It is the perfect event for the whole family to enjoy. Since 1947, this favorite annual tradition has entertained guests with a stunning display of expertly designed parade floats, krewes, marching bands, dance units, and community groups.

Festivities line the 1.5-mile parade route, beginning at Bay to Bay Blvd & Bayshore Blvd and stretching to Edison Ave. The event is alcohol-free, making it a family-friendly atmosphere everyone can enjoy.

🏴‍☠️De Soto Grand Parade

📅 April 25, 2026
📍 Bradenton, Florida
🔗 Official Site: desotohq.com

The De Soto Grand Parade held annually in Bradenton, Florida is one of the largest and oldest parades in the Southeastern United States.

Over 100,000 people line the streets of Bradenton to see Hernando de Soto, Captain of the Crewe, and their newly crowned Queen and Princess. Enjoy illuminated floats and collect beads, coins, and other fun items throughout the pirate-themed parade.

It’s a lively, family‑friendly celebration with a strong local tradition — and a must‑see for anyone who loves pirate‑themed fun.

Homosassa Pirate Invasion

📅 February 16, 2026
📍 Crumps’ Landing, Homosassa, Florida
🔗 Event Info: crumpslanding.com /pirate-invasion

Now in its 4th year, the Homosassa Pirate Invasion is a charity‑driven event supporting local Citrus County projects. Past proceeds have funded community improvements like the playground at Homosassa Heritage Park.

Enjoy live music, local vendors, food, crafts, and plenty of pirate‑themed activities. Pirate costumes are highly encouraged — and kids love this one.

 🏴‍☠️ Treasure Coast Pirate & Seafood Fest – Fort Pierce 

📅 February 2026 (dates TBA)
📍 Fort Pierce, Florida
🔗 Event Updates: treasurecoastpiratefest.com

This popular festival is expected to return in 2026 with pirate encampments, ship displays, weapons demonstrations, treasure hunts, costume contests, and live entertainment.

You’ll also find some of the best seafood on Florida’s east coast, making it a perfect blend of pirate fun and coastal flavor. Admission is typically free, with a small, suggested donation.

🏴‍☠️Pirates of the High Seas Fest – Panama City Beach

📅 October 9–11, 2026
📍 Panama City Beach, Florida
🔗 Official Site: visitpanamacitybeach.com/piratesofthehighseas

The annual pirate event in Florida happens October 9th-11th at Panama City Beach. The festival celebrates the legacy of pirates who once wandered the Gulf of Mexico and the Emerald Coast. It is characterized by storytelling and exciting staged pirate battles. You can enjoy in-person treasure hunts, online costume contests, fireworks, pirate activities, and more. 

It’s one of the most immersive pirate events in the state — and a great excuse for a beach getaway.

🏴‍☠️Billy Bowlegs Festival – Fort Walton Beach

📅 May 15, 2026
📍 Fort Walton Beach, Florida
🔗 Official Site: billybowlegsfestival.com

Billy Bowlegs Festival is a whole weekend pirate event that happens in May at Fort Walton Beach, Florida. You will have a chance to try craft beers from local brewers and enjoy delectable dishes. In addition, you can enjoy pirate activities as simulated by the pirates. Don't worry about the kids; they will have a children's pirate play zone. It’s a full weekend of pirate fun that appeals to all ages.

 🧜‍♀️ Mermaids & Pirates & Seafood, Oh My! – New Smyrna Beach, Florida

📅 February 28, 2026 – 10:00 Am – 3:30 PM
📍 Marine Discover Center – 520 Barracuda Blvd, New Smyrna Beach, Florida
🔗 Official Site: 5th Annual Mermaids & Pirates & Seafood Oh My! - NewSmyrna, FL - Community Calendar - Pyracy Pub

A family fun festival featuring mermaids, pirates, vendors, local businesses, entertainment, music & food trucks. Dress in your best pirate garb or mermaid attire for the occasion!

🏴‍☠️Old City Pirate Day — St. Augustine, FL

📅 2026 Dates TBD
📍 Colonial Quarter & St. George Street, St. Augustine, FL 32084
🔗 Official Site: Old City Pirate Fest | Visit St. Augustine

Hosted in the nation’s oldest city, this event features a Thieves Market, pirate vendors, blacksmith demos, and live entertainment. A great choice for families looking to pair history with pirate fun.

🏴‍☠️ BONUS — Pirate Adventure All Year Long!

🐊 Smugglers Cove Adventure Golf —  Southwest FL

Can’t wait for the next festival? You don’t have to.
At Smugglers Cove Adventure Golf, the pirate life is always in full swing across our five award‑winning Southwest Florida locations. Costumes are welcome, fun is guaranteed, and our crew is always ready to host you and your scallywags for a buccaneer‑worthy day out.

Each course features:

• A full‑size pirate ship
• Mysterious caves
• Waterfalls and lush tropical landscapes
• Skeleton crews guarding hidden treasure
• And yes — LIVE ALLIGATORS you can feed with a cane fishing pole

Whether you’re a pirate at heart or simply looking for unforgettable family fun, Smugglers Cove delivers an adventure for all ages, all year long— 7 days a week.

Plan your visit today: smugglersgolf.comsmugglersgolf.com

Whether you’re chasing treasure, tall tales, or just a good time with family, Florida’s pirate festivals offer adventure around every corner. Here’s to a year filled with discovery, laughter, and a little bit of pirate shenanigans along the way.