Cut a head of iceberg lettuce in half. Peel off a few outer leaves. Place lettuce cut-side down in your planter.
Cut honeydew in half and scoop seeds from one half. Slice off peel, then cut melon into 1-inch leaves. Place at edge of container.
Cut peel off pineapple, then cut fruit crosswise into 3/4-inch slices. Use a 1-1/2-inch cookie cutter to remove tough core.
Cut cantaloupe in half; scoop seeds from one half. Use same cutter to make circles. Press them into center of pineapple slices.
Insert skewer into lettuce, then slide fruit onto skewer. On additional skewers, thread 4 to 5 grapes or a strawberry.