Transfer all plants, soil and gravel from your planters to temporary pots or growing trays. Wash the insides of the planters with clean, moist cloths. Lay drop cloths on a flat, even working surface and move your planters onto the drop cloths.
Put on your rubber gloves and goggles before you mix TSP or a similar strong detergent with water in a pail or mixing vessel according to package instructions. Scrub the exterior surface of your planters with the detergent solution to remove all surface dirt. Scrub the interiors of the planters as well only if you intend to repaint them; otherwise, just make sure that the inner lips of the planters are clean so that debris aren't accidentally deposited on the surface to be painted.
Wipe the planters dry with soft, clean cloths. Allow them to dry in the sun if they still remain moist to the touch, which is rare as only very damaged glaze absorbs water.
Lightly sand all surfaces to be repainted with fine-grit sandpaper or a fine sanding block. Wipe the sanded surface with a tack cloth to remove sandpaper and old finish residue.
Spray or brush an even coat of a flat finish, stain-hiding, oil-based primer onto all surfaces to be painted. Allow it to dry according to package directions.
Paint over the primer with a spray or regular oil-based gloss or matte paint. Use a natural-bristle brush if you're painting with regular paint and clean the bristles with mineral spirits whenever the brush becomes soaked with paint. Spray several light coats rather than one heavy coat of spray paint.
Allow the paint to dry for about three to five hours or according to package recommendations. Follow up with additional coats of paint if you can still see the layer of primer. Cover the paint with an acrylic sealer spray or brush on sealant for added durability if you wish.
Replant any plants or flowers 24 hours or so after you complete the entire repainting process.