Make sure the sandbox is completely clean before you start painting it. I hosed mine off in the backyard and then gave it a once-over with a disinfectant wipe to make sure any dirt or residue was gone.
My ultimate secret for getting paint to really adhere to almost any surface is automotive primer. Coat the sandbox and lid in a layer of automotive primer, then let it dry completely.
Start painting the sandbox in your color of choice. Make sure whatever spray paint you choose says it will bond to plastic.
Paint the lid of the sandbox the same color that you painted the base of the sandbox. Just paint along the grooves of the lid for now, since the raised portions of the lid will be different colors when you are done.
After the lid paint is completely dry, start taping off the individual sections of the lid with painter's tape.
Before you paint each section, protect the rest of the lid from over spray by laying out pieces of newspaper or paper towels.
Fill in the taped off section with spray paint, then remove the tape right away before the paint has a chance to dry. Repeat steps 5-7 until all sections of the lid have been painted.
Grab your black paint pen and fill in the eyes on your turtle sandbox. Once all of the paint has dried, fill the sandbox with sand and you are ready to play.
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