We, as in Pensacolians in general, know how to throw a party, shindig, soiree, gathering, bash, gala, jubilee – you name it and we’ve got it! It would only seem right that we’d throw a party to celebrate the city itself!

The Fiesta of Five Flags Celebration it all about the heritage of our beloved city. I’ll let you in on a little secret: For a few years, I worked for Fiesta of Five Flags so you’ll get the inside scoop on these must-see events.

What you need to know: Pensacola was founded in 1559 by Spanish explorer and conquistador Don Tristan de Luna y Arellano, who we call DeLuna. He was sent on an exploration to establish a Gulf port and brought along 11 ships and around 1,500 people into Pensacola Bay. Unfortunately, shortly after that, a hurricane hit and sunk the colony’s supplies, which were still on their ships. Pensacola would later be reestablished.

Since 1559, five governments have ruled over the city: Spanish, French, British, Confederate and United States – hence why we are known as the City of Five Flags.

City of Five Flags

Fast forward to the 1940’s where Pensacola community leaders gathered together and developed the idea of an annual festival to promote their beloved city. The goal was to celebrate Pensacola’s historical background as America’s oldest city, founded by DeLuna in 1559, and encourage people to travel to visit. It has been told that during the first Fiesta of Five Flags celebration, there was nowhere for people visiting to stay, so residents opened up their homes to visitors to come join in on the festivities.

Today, the Fiesta of Five Flags celebration continues to highlight the rich heritage of the city and honor the countries that helped shape Pensacola into the diverse city it is now. Events have varied over the years as there use to be pageants, skiing competitions, and even a treasure hunt for actual treasure buried on Pensacola Beach. While the events may change, the reason for the celebration will always remain.

For the first two weeks of June, Pensacola marks the arrival of the annual Fiesta celebrations — with parades, parties, ceremonies and balls intended to commemorate our city’s rich culture.

Fiesta

If you’re visiting during the first two weeks of June you might stumble upon a gathering of a group in period clothing – that’s the royal court of DeLuna (knights, princesses and children) so don’t be alarmed --- they are here to celebrate! One of those ways is a during a grand parade!

Who doesn’t love a parade? The Grand Fiesta Parade is full of colorful costumes and plenty of people watching. Local organizations and Mardi Gras Krewes get together to parade through the streets of Downtown Pensacola in their rich party attire. You’ll see plenty of kings and queens, some rowdy clowns, go-go girls, pirates, conquistadors and more. Every year, a new Grand Marshall is chosen from local celebrities and dignitaries. Pensacola’s hometown heroes, the Blue Angels, have been honored in the past. Everyone knows the best reason to attend – the parade throws. Pensacola doesn’t skimp either. There are plenty of beads (big and small), stuffed animals, moon pies and sometimes even ice cream sandwiches. Best of all, it’s free to attend.

One of my favorite events is the Fiesta Boat Parade and DeLuna Landing Ceremony. Around 25 boats are decorated and parade across the Santa Rosa Sound in a single file line to Pensacola Beach. The best place to view the parade of boats is Pensacola Beach Quietwater Boardwalk. Once the boats dock, a landing ceremony will begin. While this ceremony is supposed to mimic the historic arrival of the Spanish to our shores, it is a very lighthearted reenactment of what might have happened when DeLuna first landed his boats in 1559. When I say lighthearted, I mean it. It’s not remotely historically accurate because it’s intended to bring a smile to your face through the narrator’s commentary.

Fiesta Boats

It’s a sight to see, with princesses and knights dressed in period costumes, along with DeLuna and his queen. While you’re out on the boardwalk, you might hear a few jingles and bells and see a brightly colored feather or two. Migrate toward those bells, as I’m sure you’ll find some happy and fun revelers. Those dressed in feathers and bells are known as the Mayoki Indians, a local Mardi Gras krewe. They will be a part of the Landing Ceremony with DeLuna and even have a fun dance or two.

Ready to celebrate the history and heritage of Pensacola through these fun themed events? Join us in early June to help celebrate our historic city and find out why visitors have been coming to our shores for more than four centuries.