A multiple plant container self-watering system comprises a primary container at a first elevation and a plurality of secondary containers at different elevations, fluidly connected by means of tubing. The primary container comprises a primary outer shell that encloses a primary reservoir pot, having an expanded upper portion and a tubular lower portion, a primary wick and a primary grow pot. Each of the plurality of secondary containers comprises a secondary outer shell that encloses a secondary reservoir pot having an expanded upper portion and a tubular lower portion, a secondary wick, and a secondary grow pot. The diameter of the lower portion of the primary and secondary reservoir pot is greatly reduced in comparison to the diameter of the upper portion thereof, thereby allowing for substantially similar dry-down time for a plurality of fluidly connected plant containers at different elevations.