(727) 742-6713

Employee Appreciation

Show your employees you care
bring magic shows and balloon hats to the office.

Book Now

Balloon Decorations

Set the stage with our impressive
balloon displays and decor.


Fundraisers and Events

See what Winking Derby can
do for your charity or event

Learn More

Corporate Events

Winking Derby entertainers travel around the world

providing innovative keynote presentations..

Learn More

Magic Up Close

Infotainers can enhance Trade Shows and Product Launches with up close and personal magic.

Learn More

Mermaids at Sunset

Stop by the Sand Pearl on Clearwater Beach and witness our one of a kind living breathing Mermaids. Or book your own for your next party!

Learn more

Stage Shows

Larger than life balloon
entertainment and charming comedy shows

Book Now




Winking Derby Event Entertainment Services – Blowing away the Competition for years.

Interactive Workshops & Presentations

Liven up that stuffy corporate conference with our amazing corporate event entertainment: Blew Out The Box creativity workshop.  Engage your audiences with this interactive and inspirational event.

Trade Shows & Inflated Marketing

Winking Derby provides trade show event entertainment and magic shows throughout Tampa, Clearwater and St Pete. Draw attention to your products at your next trade show with one of our entertainers.

Stage Shows and Productions

Winking Derby often collaborates with local museums and cultural arts centers to produce breathtaking stage shows.  Our entertainers blend larger than life balloon creatures and charming humor in our one of a kind stage productions.

Balloon Displays and Decor

Set the stage with our impressive balloon displays and decor.  Our event entertainment consultants and balloon artists provide balloon installation pieces that make any party or event truly memorable.

Balloon Fashion

Be a show stopper with our spectacular balloon dresses, outfits and costumes.  Promote your event or fundraiser, or be the belle of the ball — our balloon dress with leave a lasting impression on any audience.

Charity Events

Pop-able balloon dresses are smart, creative and exciting! One of our charities raised over $3,500 with our pop-able balloon dress event entertainment — how much could you raise for your event?

Sunset Mermaids at the Sandpearl

Stop by the Sandpearl Resort Saturday evenings to see a gift from the deep.

Every week Winking Derby sponsors story time and pictures with our Mermaids every Saturday evening at the Clearwater Sand Pearl Resort.  Entertain the children and bring the magic of Weeki Wachee Mermaids to your next birthday party or pool party.  Contact us now and see how you can make your next children’s party a lasting memory!

Contact Us

Balloons Inflated

Prize Balloons Popped

Miles Travelled

Smiles Made

Blew out of the Box

Captivate your audience at your next in-conference with a tailor made break out session or interactive presentation.

Blew out the Box is a complete and innovative creativity workshop that delivers a unique experience directly to your venue.  Combining humor, creative outlets and hands on activities, Blew out the Box breaks up the monotony of the day, allowing your audience to recharge and refocus on the task at hand.

Watch Video

Blew out of the Box Stats

Fun & interactive 95
Inspirational 80
Hands On 100

Book an Entertainer

To book an balloon artist, magician or performer, call us at 727-742-6713 or

Book Online