Add the pineapple chunks with juice and the sweetened condensed milk to your blender. Blend until no chunks remain, about 30 seconds.
Continue with an ice cream maker
Transfer to a container and chill in the refrigerator until it reaches 40 degrees Farenheit, or at least 4 hours. You can leave it in the refrigerator overnight.
Add your chilled pineapple juice to the ice cream maker. Churn (stir setting) until it is the thickness of soft serve ice cream, 18-22 minutes.
It is best served immediately*. Or, transfer to a container you can freeze, cover with parchment paper or a lid, and freeze.
Continue without an ice cream maker**
Add it to a zipper bag, seal it, and freeze it flat. OR freeze it in mini ice cube trays. Once frozen, break it up into chunks, and blend it until smooth. The texture, in my opinion, leaves much to be desired.
Scoop or pipe using a star piping tip.
Video
Notes
* If you choose to freeze the Dole whip, it will harden. You will end up with more of a pineapple icy than the soft-serve texture of Dole whip.** Another option if you don't have an ice cream maker is to use the method Disneyland shared with the world in 2020: Add 2 cups frozen pineapple (canned or fresh), 4 oz. pineapple juice, and 1 large scoop of vanilla ice cream to a blender. Freeze overnight in a sealed container to scoop or pipe.