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Del Webb Orlando
500 Del Webb Blvd
Davenport, FL 33837
(863)424-5050
Montecito Clubhouse Hours
Daily 7am to 9pm
Friday 7am to 10pm
LaTapenade Tavern Hours
Wed thru Sunday noon to 8pm
Friday noon to 10pm
(863)356-5979
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Pirate Regatta

Date and Time

Saturday, August 29, 2026, 1:00 PM until 5:00 PM

Location

Pool area and grass area
FL  
USA

Event Contact(s)

Amber Pearce
Lifestyle Manager

Category

Lifestyle - Entertainment

Registration Info

Registration is required

Capacity

15 Total Slots
12 Available Slot(s)

About this event


Pirate Regatta

Ahoy, mateys! Join us for an afternoon of pirate-themed fun, friendly competition, and unforgettable adventures at the Pirate Regatta!

Cheer on your fellow residents as they race their handmade cardboard boats across the pool in a battle for speed, creativity, and pirate glory. Then watch as hundreds of rubber ducks set sail in the Rubber Ducky Race, competing for treasure and bragging rights.

Whether you're racing, cheering from the sidelines, or simply enjoying the excitement, the Pirate Regatta promises laughter, community spirit, and plenty of swashbuckling fun for all.

Event Schedule

  • Cardboard Boat Race – 1:00 PM
  • Rubber Ducky Race – 3:00 PM

See the HUB for registration details, race rules, and participation information. Arrr you ready for the adventure?

Cardboard Boat Race

Part of the Pirate Regatta
Saturday, August 29 | 1:00 PM

Ahoy, Captains! Gather your crew, build your vessel, and prepare to set sail in the Del Webb Orlando Cardboard Boat Race. Whether you're racing for victory, showing off your creativity, or simply hoping to stay afloat, this event is all about teamwork, creativity, and pirate spirit.

Boat Construction Rules

  • Boats must be constructed primarily of corrugated cardboard.
  • Cardboard may be folded, layered, bent, and shaped as desired.
  • Duct tape, packing tape, masking tape, and waterproof tape are permitted.
  • Paint, markers, and decorations are encouraged.
  • Boats must be human-powered only.
  • Boats may be built at home and brought to the event.
  • Maximum of 2 crew members per boat.

Prohibited Materials

The following materials are not permitted:

  • Wood
  • Metal
  • Fiberglass
  • Plastic sheets or panels
  • PVC pipe
  • Pool noodles
  • Inflatable devices
  • Foam flotation devices
  • Styrofoam
  • Pre-manufactured boat parts
  • Motors, sails, or mechanical propulsion systems

Team Requirements

  • Maximum of 2 residents per boat.
  • Teams must provide a boat name.
  • Pirate-themed decorations are encouraged.
  • Pirate costumes are encouraged but must not interfere with safety.
  • Work together to design, build, and race your boat while demonstrating teamwork, creativity, and good sportsmanship.

Teamwork

The Cardboard Boat Race is all about working together. Crews should communicate, encourage one another, and combine their creativity and problem-solving skills to build a boat capable of crossing the pool. Whether your boat races to the finish line or becomes a legendary shipwreck, teamwork, sportsmanship, and having fun are what make this event a success.

Race Rules

  • All boats must pass inspection before racing.
  • Boats must start behind the designated starting line.
  • Crew members may propel the boat using only their hands or paddles.
  • Team members should remain with their boat throughout the race whenever possible.
  • Unsportsmanlike conduct may result in disqualification.
  • Event officials reserve the right to disqualify any unsafe boat.

Participant Safety Requirements

  • Participants must know how to swim.
  • Participants enter the water and race at their own risk.
  • Participants must be able to safely enter and exit the pool without assistance.
  • Any participant displaying unsafe behavior may be removed from the race.
  • Event officials reserve the right to remove any participant or boat for safety reasons.

Awards

  • Fastest Ship
  • Best Pirate Theme
  • Most Creative Design
  • Best Crew Spirit
  • Most Spectacular Sink
  • People's Choice Award

Registration

Registration is required through the HUB. Space is limited.

Will your ship sail to victory or become a legendary shipwreck? There's only one way to find out!


Rubber Ducky Race

Part of the Pirate Regatta
Saturday, August 29 | 3:00 PM

Ready... Set... Splash!

Adopt your lucky duck and cheer it on as it races across the pool in the Del Webb Orlando Rubber Ducky Race! This lighthearted event is all about fun, friendly competition, and seeing whose duck will paddle its way to victory.

Duck Adoption Rules

  • Each registered resident may adopt one (1) rubber duck.
  • Ducks will be assigned a number before the race.
  • Residents may name their duck.
  • Ducks may not be exchanged after registration.

Duck Rules

  • Ducks must remain in their original condition.
  • No weights, motors, magnets, or alterations that could affect performance.
  • No decorations or modifications that change the duck's size, buoyancy, or ability to float.

Race Rules

  • All ducks will be released at the same time from the designated starting point.
  • Once the race begins, ducks may not be touched, pushed, or assisted in any way.
  • Event staff will oversee the race and determine the official results.
  • The first duck to cross the finish line is the winner.
  • All decisions made by event officials are final.

Good Sportsmanship

The Rubber Ducky Race is all about having fun, cheering on your neighbors, and enjoying a little friendly competition. Whether your duck finishes first or last, every participant is encouraged to show good sportsmanship and pirate spirit.

Awards

  • First Place Duck
  • Second Place Duck
  • Best Duck Name
  • Lucky Duck Award (random drawing)

Registration

Sign up the day of the race. Each resident may adopt one duck. Space is limited.

Will your lucky duck race to victory and claim the treasure?