Because the plants in a strawberry pot are planted one on top of the other, it can be tricky to water the whole pot. Either only the top plants get watered or the bottom plants are left sitting in water. Don't try to get around this by water each individual opening, you'll just wash away the soil. The best method for insuring the entire pot of plants gets watered well is to insert a pipe into the center of the pot while planting. I've listed this as optional, but it will make watering much easier and more efficient in the long run.
To create a watering pipe, measure the length of your strawberry pot and then cut a piece of PVC piping 1-2 inches shorter. A pipe about 1 ½ inches in diameter works well for most size pots.
Next drill a series of 1/8 to 1/4 inch holes into the PVC pipe, using your hand drill. Space them randomly around the pipe, about 1 ½ to 2" apart.