Blend the pineapple in a food processor until crushed. Do not strain.
Add sugar, rum and ice.
Add coconut milk by the 1/2 cup depending on how creamy you want it (I added the entire tin).
Pour over ice in a jug and serve immediately.
Substitute: If you want a thinner drink, double the pineapple, strain them and do not add coconut milk.
Notes
A delicious and thick cocktail that’s perfect for a hot summer day. I used coconut milk and rum instead of coconut rum to thin out the pineapples since they weren’t strained. You can adjust your level of sweetness. Prepare this right before you will serve it.