Fun Holiday Events in Pensacola, Destin, and More ~ The Southern Scoop’s Featured Events

With Thanksgiving and Christmas right around the corner, we’ve got the holidays on the brain! There’s never been a better time to start planning your beach vacation. There are so many fun holiday events, in Pensacola, Destin, and all along the Gulf Coast that we’re sure it will be hard to decide just where to begin! If you’re adventurous, you can stay all across the Gulf Coast in your Pensacola Beach vacation rental for two nights, then two nights in Fort Walton Beach, two nights in Destin… you get the picture. This way, you can experience a little bit of everything the areas have to offer! Check out some of our favorite fun holiday events below that serve as the perfect accompaniment to your holiday vacation.


Hangout Oyster Cook-Off Craft Spirits & Beer Weekend, 2019

Don’t take our word for it, but oysters, craft spirits, and beer are a match made in heaven. From November 1-2, head down to The Hangout in Gulf Shores, Alabama for one of the Gulf Coast’s most popular events. A mix of celebrity chef demonstrations, tastings, oyster shucking contests, and more await. In addition, you’ll enjoy live music, family-fun events, and an oyster showcase bar featuring oysters from the Pacific Northwest, New England, the Maritimes, British Columbia, the Mid-Atlantic, Baja Peninsula, and the Gulf of Mexico. You won’t believe all the fun there is to be had! Get tickets for this event here.

2019 Frank Brown International Songwriters’ Festival

A highly anticipated event all across the Panhandle, the Frank Brown International Songwriters’ Festival is one of the most fun holiday events in Pensacola. Spanning across venues from Pensacola and Perdido Key, Florida to Orange Beach, and Gulf Shores, Alabama, over 200 nationally-acclaimed songwriters will perform some of your favorite top hits. You’re sure to be surprised at some of the talented minds behind these songs! Artists from the Songwriters’ Festival have even gone on to become Grammy award-winning artists. When booking your vacation rental in Pensacola Beach, Perdido Key, Orange Beach, or Gulf Shores for the festival, be sure to use promo code FrankBrown at checkout to save 10%!

Rosemary Beach Holiday Market

What better way to prepare for the holidays than with the Rosemary Beach Holiday Market? This is a great opportunity to pick up some handmade crafts for stocking stuffers or presents under the tree. On November 16th from 9 AM until 4 PM, Rosemary Beach Town Center is filled with vendors showcasing their handmade art, furniture, jewelry, and more. You’ll even get the chance to enjoy the town’s Christmas tree lighting, merchant open house, a bocce tournament, and breakfast with Santa. This is sure to get you in the holiday spirit!

30A 10K

Also taking place in Rosemary Beach, the 30A 10K race is a time-honored Thanksgiving tradition. What better way to work up an appetite for some turkey and pumpkin pie than participating in a 10K? If a 10K isn’t quite your speed, there is also a 5K and a 1 mile fun run. The race takes place Thanksgiving Day in Rosemary Beach Barrett Square at 7:30 AM, with the 5K beginning at 9:30 AM and the fun run starting just after the 10K. The best part of the 30A 10K? The race has been able to donate over $350,000 to local Gulf Coast charities in its eight years. It also promotes health and fitness, so you can feel even better about participating!

2019 Foo Foo Fest

Don’t let the name throw you off – Foo Foo Fest is one of Pensacola’s most anticipated events. Foo Foo Fest showcases the rich culture and artistry in Pensacola, “delivered with a hefty dose of Southern sophistication.” The festival consists of a bunch of events spanning from October 31st to November 11th, including the Great Gulf Coast Arts Festival and the Frank Brown International Songwriters’ Festival. In addition, “Women of Fire” will perform fire displays, while the Blue Angels put on their homecoming airshow at NAS Pensacola. There’s something to do each day during Foo Foo Fest! Learn more here.


A Downtown Holiday

Fort Walton Beach’s December event, A Downtown Holiday, is so popular they just had to bring it back for another year! On December 7th from 11 AM – 6 PM, come down to the Fort Walton Beach Landing Park for a day full of Christmas shopping, holiday treats, live entertainment, kids’ activities, and more! There is even a tree lighting at 5:30 PM. This event is also a drop-off location for the U.S. Marine Corps’ Toys for Tots program. If you are coming to A Downtown Holiday, please bring a new, unwrapped toy to help a child in need have a truly Merry Christmas this year.

33rd Holiday on the Harbor

We love lighted boat parades in Destin, and Holiday on the Harbor is no exception. On December 8th, the Destin Harbor is alight with ships decked out in their best Chirstmas garb – this means lights, tinsel, ornaments, and more. The best spot to watch the boats sail by is at Margaritaville or Harry T’s at HarborWalk, so be sure you get there early for the best vantage point! From 1-8 PM, you’ll have the chance to visit with Santa, see a special performance of the Nutcracker, and even a fireworks show.

Sinfonia Holiday Pops with Matthew Morrison

Get into the holiday spirit with Sinfonia’s Holiday Pops with Matthew Morrison. That’s right; the Tony, Emmy, and Golden Globe-nominated actor is joining Sinfonia’s full orchestra for an evening full of festive holiday medleys. Come down to Village Baptist Church in Destin on December 13th at 7:30 PM for a night full of holiday cheer! Morrison will also perform some of his hit songs throughout his extensive career, including ones performed during his time on Fox’s musical comedy series “Glee.”

34th Annual Christmas Lighted Boat Parade

Can’t make it to Holiday on the Harbor in Destin? No worries; catch the 34th Annual Christmas Lighted Boat Parade in Gulf Shores on December 14th! The boats begin their journey at Lulu’s in Gulf Shores at 5:30 PM, then traveling east down the Intracoastal Waterway. The route takes them all through Ono Island, the Perdido Pass, Terry Cove Harbor, and ending right at Flora-Bama. Set up your blanket or lawn chair at any of these points to see some beautifully-decorated boats and get into the festive cheer! With over 40 sailboats, sportfishing boats, and kayaks, this is one of the largest boat parades in the Southeast!

Flora-Bama’s Annual Santa Drop

You aren’t misreading that – the Flora-Bama’s Annual Santa Drop is exactly what it sounds like. This is the perfect kickoff for the holiday season, with Santa skydiving onto the white sandy beaches just behind the Flora-Bama. Once Santa lands, you’ll have the chance to visit with him while enjoying free treats, live entertainment, and even Christmas carols.

We hope you enjoyed learning about some fun holiday events in Pensacola, Destin, and more of our areas across the Gulf Coast! If you’re planning your holiday vacation in Pensacola Beach or anywhere across the Gulf Coast, be sure to check out our Gulf Coast vacation rentals for the best rates and local Southern customer care. We’ll see you next month with another Southern Scoop blog!