Cut wine barrels in half to produce smaller, more manageable planters. Cut the top half off the barrel off and turn it over for a second planter, or cut the barrels in half from top to bottom to produce longer, more shallow planters.
Drill four to five holes in the bottom of each wine barrel planter for drainage. Plants and vegetables suffer in muddy soil or standing water but thrive in any container with adequate drainage and nutrition.
Waterproof the wood for more protection. Without waterproofing, water will seep into the wood and warp it over time. Paint the inside of the barrels with non-toxic waterproofing solution, and paint the bottom 6 inches of the outside surface.
Lay 4 to 5 inches of brick, stone or gravel in the bottom of each barrel. This foundation fills space more cheaply than soil and encourages the best possible drainage.
Mix a potting soil of 1 part organic compost to 1 part garden loam for moist, nutritious and quick-draining foundations. Potted plants require better nutrition and moisture in their soil, as they have limited access to fresh soil and dry more quickly. Fill each barrel planter to within 2 inches of the top with this mixture, then add 5-10-10 or 10-10-10 fertilizer. Plant according to your personal tastes.