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  • May 9, 2025

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Cool Kids Italian Water Ice Ditches Day Jobs to Introduce New Frozen Flavors to Milwaukee

September 4, 2021

By Dylan Deprey

The Keys family is bringing a new flavor to frozen treats in Milwaukee. (Photo by Dylan Deprey)

Looking into Summer 2021, the Keys family needed to makes some tough decisions.

Between raising their four children and working in questionable COVID-19 conditions, Alvin and Jasmine Keys were at a crossroads.

“We were in between things, and we thought ‘What could we possibly do as business owners?” Alvin Keys said. “We wanted something where we didn’t have to be indoors and could still be six feet apart. It was like, do we have to work for other people?”

They started researching and it eventually ended up between two food stands: funnel cakes or Italian ice.

While funnel cakes were a Wisconsin fair staple, between the over-saturated market and hot conditions, introducing Italian ice to a new market seemed like the challenge they were looking for.

“Italian ice is one of those things that once I get you to taste it, you’re going to love it,” Alvin Keys said. “We jumped on board for this, and business has been great.”

Before the lime green trailer popped up at local festivals and in parking lots across Southeastern Wisconsin, Jasmine Keys found it on Facebook marketplace. All it took was some cleaning, a few modifications and a little razzle dazzle.

On a hot day, it’s almost hard not to dive right in to an ice cold Italian ice. (Photo by Dylan Deprey)

“It didn’t look like this when we got it, so my husband and I revamped it,” she said. “We painted it, laid down flooring, did all the stickers and decals—and we’ve been up and running since.”

The Keys family unveiled officially Cool Kids Italian Water Ice to Milwaukee during the 2021 Juneteenth Celebration, and have been grinding ever since.

Along with catching the tail end of festival season, Cool Kids Italian Water Ice has been popping up around the city. The trailer’s location is posted on social media along with when it’ll pop up and how long it’ll be there.

On a 90-degree day in mid-August, a small line formed alongside the trailer in the parking lot near 103rd Street and Silver Spring Drive in Milwaukee. The rainbow colored “Italian Ice” flag waved in customers as the family pumped out gallons of Italian ice

Their oldest son, Josiah handed out ice cold confections to happy customers, as their eldest daughter took her turn watching the younger two children Jayda and Aubri.

“The kids love coming, even the 4-year-old wants to come and help serve the customers,” Alvin Keys said. “There are some days when they get mad [that] they can’t come.”

It’s all hands-on deck when it comes to customer service at Cool Kids Italian Water Ice. (Photo by Dylan Deprey)

From strawberry lemonade and mango madness, to tropical rainbow and cherry bomb, the delicious dessert is a blast of flavor that satisfies the palate on a scorching Wisconsin summer day. Fans can combine any of the 10 flavors to create any concoction they wish.

Along with pop-ups, Cool Kids Italian Water Ice does birthday parties and other small events. Although its only one trailer at the moment, the Cool Kids are looking forward to building its Italian ice arsenal and sharing its unique flavors across the Midwest.

Alvin and Jasmine Keys plan on being in more festivals and events next year, and are staying out through fall, as long as people are looking for a frozen treat.

“To be able to get out with the family and introduce a new product to the city, it’s great,” he said. “We’re very family oriented, we’ll always be about family, so when we decided to do something to pass off to our children, we’re elated.”

Find Cool Kids Italian Water Ice’s next pop-up on its social media

Facebook: Cool Kids Italian Water Ice
Instagram: @coolkidsitalian

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Popular Interests In This Article: Alvin Keys, Cool Kids Italian Water Ice, Dylan Deprey, Entrepreneurship, Jasmine Keys

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