Pirate lore abounds in Florida, including the story of pirate Robert Searle who stole a Spanish vessel in 1668 and took it to raid St. Augustine and inspire the Spanish-built Castillo de San Marcos. There’s also the Spanish swashbuckler Jose Gasparilla, among others. All have inspired annual reenactments and events across the state. 

Yes, we have fun in Florida and it gets wild with so many fairs and festivals in Central Florida and across the state. 

Curious to find some fairs and festivals near you that you can take the whole family to?

To help, we’ve put together five fun picks for you. Keep reading to see which jump out at you that you think your kids will love too and then get them on the calendar.

1. Gasparilla Pirate Fest

This annual festival swarms Tampa with many a seafarin’ pirate and boatloads of fun for the whole family. 

The festivities revolve around the storming of town by pirates and the big pirate parade that happens on the last Saturday of January down historic Bayshore Boulevard and into downtown Tampa. Both activities are free to the public.

A week earlier there is also the Gasparilla Children’s Parade, and two weeks after is the Sant’Yago Illuminated Knight Parade. It’s a whole month of pirates and knights!

Gasparilla Invasion

Parade day starts with a reenactment of the invasion of Tampa by pirates. The boats they sailed in one were called the Gasparilla Flotilla with Jose Gasparilla in the lead. A complete rigged pirate ship shows up at Hillsborough Bay. Canons fire.

It heads through Seddon Channel toward downtown Tampa and its dock goal: the Tampa Convention Center. Then the Mayor cedes the key to the city.

Parade of Pirates

The parade is the victory celebration after capturing Tampa. The pirates share their loot as they travel 4.5 miles. Parade goers enjoy colorful costumes, music, floats, marching bands, doubloons, sparkly beads, and other treasure. 

2. Weeki Wachi Swamp Fest

This annual three-day festival that draws thousands of guests takes place at the start of March each year. It started in 1994 as a fundraising event and has moved around the area a lot. It currently takes place at Linda Pedersen Park. 

Expect plenty of fun, including food, craft sellers, and family-friendly contests and entertainment. There are the Swamp Monster costume contests where everyone goes nuts with their personal rendition of a swamp monster. There is also a swamp and critter T-shirt design contest and a raffle. 

Enjoy live music, including instrumentals, country music, and folk music, and dance performances. Enjoy craftspeople selling their handmade wares, with everything from clothes, jewelry, and sweets to soap, baskets, art, and pottery, to name a few. And enjoy delicious goodies, including swamp dawgs (gator on a stick); swamp biscuits and gravy; chicken sandwiches; Cuban sandwiches; Italian sausage; blooming onions; and strawberry ice cream.

3. Florida Blueberry Festival

This four-day festival in Kissimmee takes place at the end of March each year. It’s been around since 2011 and celebrates the glorious fruit that pops on the scene each spring. 

Enjoy everything blueberry, including blueberry pie, blueberry honey, blueberry shortcake, blueberry plants, and blueberry jam to get you started. And, of course, enjoy fresh Florida blueberries!

Take your kids over to the Blueberry Patch Kids Zone for bounce houses, rock climbing, bungee jumping, and all kinds of kid activities for all ages.

There’s also live music (18 bands and other performers!) and a food court for the whole family. Grownups can also enjoy an award-winning blueberry wine and fruit wines plus a beer garden. 

Tampa Bay Magazine hosts a juried art show with a $6000 prize and craft vendors if you’re interested in arts festivals or local craft fairs. 

4. Cocoa Beach Pirate Fest

Enjoy three days of family fun at the International Palms Resort in Cocoa Beach. This annual festival is 7 years old and takes place on the first weekend in June. Kids and the whole family enjoy treasure hunts and arts and crafts. Visit the living history pirate encampment and explore pirate ships. 

There is tons of great food and drink. Think pirate-themed vendors at their best. There are also more kid-focused activities. And you grownups get to enjoy two adult-only parties: the Pirate Party on Friday night and the Pirate’s Ball on Saturday night.

Yo ho ho, good times for all! 

5. Florida Kids and Family Expo

Expect two days of family activities that you and your kids will love at Orange County Convention Center. Expect to learn about businesses and organizations in Central Florida too, like products, services, and more, that can make your experience living in the area better. Think education and tutoring services or extracurricular and enrichment activities.

That’s the goal of the two local moms that started the event in 2014: exposure to local things you need plus fun-filled activities for your kids.

The Activities for Kids

Your kids won’t be able to do everything because there is so much! You can get in on the fun too. Enjoy laser tag, bounce houses, and a zip line. Ride the mechanical bull.

Play sports. Win prizes. Wrestle. Enjoy the petting zoo.

Get your face painted. Do arts and crafts. This is just a sliver of what’s offered, and it’s all indoors.

The Expo

You may think you know everything about Central Florida and how basic services function, but we bet you don’t know everything. Let’s see if we can stump you. Can you name two alternative education options in the area? Florida Virtual School Full-Time and Charter Schools USA.

Can you name a telecommunication company in Florida and a global provider of telecommunication equipment? Central Florida Cable Communications, Spectrum, Cox Communications, and Xfinity answer the first. And you get extra points if you got the second, which is something you may not need to know if you’re an average mom in Central Florida: Rincon Technology.

There are typically over 150 exhibitors covering products and services, with everything from education options to local media. Enjoy and learn!

Enjoy Festivals in Central Florida and All Kinds of Fun

Find anything fun here that you and your kids and the whole family might enjoy? We bet you did! And there are so many more fairs and festivals in Central Florida to choose from, plus all kinds of other fabulous activities. 

There’s travel in Florida, for example. There are plenty of hidden gems in the Sunshine State. Curious? Check out these seven hidden travel gems in Florida given the exotic travel stamp.

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