Remove the wine barrel's lid, if it's attached. Use a crowbar, saw or reverse drill. The method, obviously, depends on the barrel's construction. The point is to make an open-ended barrel.
Drill 2-inch holes around the barrel's exterior. Leave 10 inches between holes and make the rows 10 inches apart. Drill in staggered rows, or rings, so that the planting holes are diagonally above and below one another. Don't worry if you can't achieve a classic diamond pattern; the barrel's metal hoops and grain irregularities will prevent perfect symmetry, and the plants will still look lovely trailing out of their irregularly spaced planting holes.
Turn the barrel over and drill five ½-inch holes at the bottom of the barrel. These will be your drainage holes.
Cut a circle of hardware cloth into a circle 1 foot in diameter. Drop this to the bottom of the barrel.
Cover the hardware cloth with 2 inches of clean gravel.
Drill or punch nail-sized holes around the PVC pipe, about 6 inches apart.
Mix potting soil with fertilizer in a wheelbarrow and keep it ready nearby.
Stand the pipe in the center of the barrel. Fill the pipe with sand. It's helpful to have a partner hold the pipe upright during the rest of this process, although bracing the pipe with boards or tension rods would also work.
Begin adding the potting soil to the barrel, firming it around the base of the watering pipe until they reach just below the first ring of planting holes.
Gently insert strawberry plants' roots through the planting holes. Try to arrange the roots into a fan shape after they are inside the barrel.
Add about 5 more inches to the barrel's interior until it reaches halfway to the next row of planting holes.
Water the soil with a low-pressure hose or watering can. Your goal is simply to add a little moisture to keep the plants going during the planting planting process, so don't actually soak the soil.
Add more soil until you reach just below the next row of planting holes.
Continue planting, filling and watering the barrel where you've inserted strawberry plants into the top row of planting holes.
Add more soil to reach just below the ring of the barrel, making sure not to cover the top of the center watering pipe. Plant more strawberry plants on top, or (if you wish) other shallow-rooted plants, such as herbs or lettuce.
Insert a hose into the watering pipe and run water for several minutes to give the strawberries a good soaking. When a finger poked into the planting holes detects damp soil around the plants' bases, turn the hose off.