Tampa’s Gasparilla Pirate Fest this Weekend

The story of Gasparilla begins with the legend of Jose Gaspar, a Spanish aristocrat turned menacing pirate believed to have terrorized the coastal waters of Southwest Florida in the late 18th and early 19th centuries. The mystical Gaspar was a well-educated, and highly-regarded officer in the Spanish Navy who left everything behind to pursue a quest for treasure. Legend states that he found his chest of gold and to this day his fortune resides somewhere along the Florida coast. While the whereabouts of that treasure remains a mystery the legend of Gasparilla remains an iconic symbol of Tampa Bay.


In 1904, to commemorate the legend, an elite group of wealthy Tampa natives formed “Ye Mystic Krewe of Gasparilla.” They adopted Jose “Gasparilla” Gaspar as patron rogue of a city-wide celebration now known as the Gasparilla Pirate Festival. For the past 100 plus years, on the last Saturday in January, Tampanians build elaborate floats and “invade” the city of Tampa via Bayshore Boulevard. They make their way from the Tampa Yacht & Country Club past the Bayshore mansions all the way downtown where the Jose Gaspar ship docks and the mayor surrenders the key to the city to the captain of Ye Mystic Krewe of Gasparilla.


Here are a few ways to enjoy this historic Tampa tradition to the fullest this year:


  • The Gasparilla season kicks off with the extravagant Gasparilla Charity Ball hosted by the Rotary Club of Tampa. This costume gala features live music by the local R&B group, The Black Honkeys, and offers VIP tickets for $125 with early entry, valet parking, an hour-long open bar, and hors d’ouerves. The sense of community is strong and profits go toward service projects, scholarships, and grants.
  • The family fun begins on the third Saturday of January with the Gasparilla Children’s Parade. This family-friendly event has been a part of the celebrations since 1947 and offers an opportunity for children to enjoy the festivities, floats, and beads.
  • On the last Thursday in January, just before the weekend festivities begin, is the exclusive Ye Mystic Krewe of Gasparilla Captain’s Ball. While this event is reserved for Krewe Members and their guests, its significance lies in the historic Gasparilla monarchy and in the tradition itself. This lavish evening is an opportunity for the Gasparilla King and Queen to mingle and dance amongst the members and celebrate the start of the Gasparilla season.


The big event, as you may have guessed, is the Gasparilla Pirate Festival also known as the Parade of Pirates or Pirate Fest. The invasion starts at 11:30 in the morning and the festivities continue for the rest of the day. While the madness can be part of the entertainment, you may prefer to enjoy the festivities more fully by eliminating the chaos.


Here are a few ways to avoid the hoards of crowds and debauchery and better enjoy the festivities:


  • Reserve a bleacher or chair spot for $50 to enjoy the best view of the parade at gasparillatreasures.com
  • Purchase a ticket to the Sunset Salsa Tent located at Nance Avenue and Albany Street. Here you can enjoy a premium view, enjoy an all you can eat buffet and an all you can drink bar with live music and a front row seat.
  • Charter a boat with Anchor Rides. If you plan to dive into some rum this Gasparilla we recommend enjoying the festivities waterside by hiring a boat or yacht. Bypass the traffic and parking madness completely with dockside pick-up from a reliable captain. Relax and join in on the fun of the boat parade.
  • Bring your own boat out. If you’re not planning to drink, then there’s no better way to celebrate the life of a pirate than on a boat. Just keep in mind that docking, especially downtown, is tricky and limited so you will likely need to stay on your boat through the duration of the celebrations.
  • Purchase a ticket to the Gasparilla Invasion Brunch Cruise. Imagine sailing right alongside the Jose Gasparilla on a yacht while enjoying drinks, brunch and music. It’s all possible with the Yacht Starship brunch for just $150 for adults and $90 for children.


The party doesn’t stop when the mayor surrenders the keys of the city to the captain, in fact, it’s just the beginning. The Gasparilla season continues all the way through early March with the Sant’Yago Illuminated Knight Parade, the Gasparilla Film Festival, the Gasparilla Festival of the Arts, the Gasparilla Distance Classic, and the Gasparilla Music Festival.

January 23, 2019