Top 10 Festivals & Events Happening on Florida's Gulf Coast During the Winter Season

Are you coming to the warm, sunny shores of Florida's Gulf Coast over the winter months? If so, here's a rundown of our favorite annual festivals, events and things to do during the winter season. As you can see, there's a lot going on, so mark your calendars and plan to attend these favorite Gulf Coast events. We promise you won't want to miss any of them.

Here is our Top 10 list of the best Florida Gulf Coast events this winter. We've kept them in chronological order for your convenience. Winter is looking brighter already!


1. Gasparilla Children's Extravaganza, Tampa Bay Gasparilla Pirate Fest Tampa Bay FL

Avast ye lads, lassies and young scallywags—this is the event for you. Set your sails toward Tampa Bay in January and come ashore for the Gasparilla Children's Extravaganza. Land ho! Ye and yer crew can join in the fun and festivities. Come dressed in yer best buccaneer garb and get ready for the parade, piratechnics, air invasion, hidden treasures and so much more. Aye!

2. Gasparilla Pirate Fest, Tampa Bay

Calling all salty rogues and lusty wenches to the Gasparilla Pirate Fest. Landlubbers beware; yer Gulf Coast shores will never be the same. Plundering, pillaging and piratical mayhem abound. The pirate invasion is just the beginning. Prepare yerself for the parade of pirates, street festival and more bootleg fun for everyone. Make sure yer sea legs are well established and come thirsty. Grog, rum and other lively spirits are a flowin'.

(We'll talk more about these two BIG Gasparilla Pirate Festival events in a later blog post. Stay tuned! For now, you can read more about the events here.)

3. Pinellas Folk Festival, Heritage Village

Pinellas County celebrates traditional folk, blue grass, gospel and country music with Tampa Bay's best musicians all in one place: The Pinellas Folk Festival at historic Heritage Village. In addition to kicking up your heels, you'll have plenty of other things to see and do including living history demonstrations, crafts and activities, storytelling and a children's stage, antique car show, sugar cane grinding and boiling, and the list goes on and on. Fun and educational; what's better than that?

4. Sunsets at Pier 60 Festival, Clearwater Beach Sunsets at Pier 60 Clearwater Beach FL

The best thing about the Sunsets at Pier 60 Festival is that it happens every single day of the year. You heard correctly, this nightly festival is a local favorite celebrating the stunning Gulf of Mexico sunsets, pristine white sands, and the laid-back beach vibe that we all know and love. Enjoy live entertainment, creative and talented buskers, vendors scattered along the pier, and fun for the whole family each evening from 4-8p.m. Special events happen here too like the free Seaside Cinema and Sugar Sand Festival, just to name a few. It's a must-see, must-do here on the Gulf Coast.


5. Sea-Blues Festival, Clearwater

Two great things that go great together: seafood and the blues. Coachman Park is the venue and general admission is offered free-of-charge to this popular two-day festival. The Clearwater Sea-Blues Festival kicks off with the Blues Walk restaurant crawl, followed by a full lineup of amazing blues performers. Dying to know who's performing at the Sea-Blues Festival this year? Click here. You're welcome!

6. Florida State Fair, Tampa Florida State Fair

The Florida State Fairgrounds play host to this beloved annual event each February. The Florida State Fair offers everything you'd expect from a state fair, and so much more! Come hungry, your favorite fair fare is sure to please. Have a deep-fried anything with a side of funnel cake, or whatever your pretty little palate desires. Want to know what's new at this year's Florida State Fair? There are more free concerts than ever, and for the first time in Florida, two new free exhibits including a traveling replica of the Vietnam Veterans War Memorial Wall and a 9/11 Never Forget Traveling Museum. Mark your calendar!

7. Florida Strawberry Festival, Plant City

You have to head inland a bit from the Gulf Coast to the Florida Strawberry Festival in Plant City, but it's so worth the trip. Luscious local strawberries are the highlight; but once you get past the strawberry tent, you'll find great live entertainment, fantastic food, kids' activities and even some celebrity appearances. The Belle City Midway is a favorite for the kids and kids-at-heart with adrenaline-pumping action in the form of rides, games and attractions. The Florida Strawberry Festival is steeped in tradition and has an interesting history. Don't miss it!


8. Philadelphia Phillies Spring Training, Clearwater

Take me out the ballgame! Get an early glimpse of the preseason action at the Philadelphia Phillies Spring Training at Clearwater's Bright House Field. The Phillies have been training in Clearwater, Florida since 1947, so it's pretty much a tradition at this point. You can find out more about the history as well as the Phillies Spring Training schedule, photos and more on their spring training website. Batter up!

9. IRB Greenfest, Indian Rocks Beach Greenfest in Indian Rocks Beach FL

In celebration of all things green, Indian Rocks Beach hosts its annual IRB Greenfest each March on the weekend following St. Patrick's Day. Eco-friendly vendors along with green good and services are the hallmark of this event. Enjoy fresh local fare, beer, wine, live entertainment and plenty of fun for the kids. Shop local at the Green Market offering organic, local and environmentally friendly products. Area non-profits are on-hand at Greenfest, too. Be sure to stop by!

10. Great American Clean Up, Indian Rocks Beach

The city of Indian Rocks Beach partners with Keep America Beautiful along with Keep Pinellas Beautiful for its annual Great American Clean Up event each March. Join in the effort (and have fun, too) to clean up the local parks, public areas and Gulf Coast waterways. Make plans to stay after the event for a bit comradery and light refreshments. Thanks in advance for keeping Florida beautiful!

Wow, that takes up to spring here in the Sunshine State. It never really feels like winter here on the Gulf Coast, so if you find yourself with a case of the Winter Blues, plan a little Florida getaway. The warm Gulf of Mexico waters, pristine white sandy beaches and sunny shorelines do wonders for the mind, body and soul. We hope to see you in the upcoming months!

What's on your Florida Gulf Coast itinerary this winter?

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