The best solution is to use ballast instead of permanent bolts. Choose a planter box with a wide, low profile and a heavy-duty recycled polyethylene, fiberglass, or concrete-composite body, then fill its internal ballast chamber with water, sand, or gravel. Water is easy to drain when you need to move the planter, while sand or gravel is better for cold climates where freezing water could damage the base. A planter with internal paver pockets is also excellent: you can drop in concrete pavers for extra weight and remove them later without drilling anything.
For mobility, look for lockable casters or retractable wheels. These let you reposition the planter for cleaning, seasonal planting, or rearranging a patio, but the brakes keep it stable in everyday wind. Avoid small, tall, lightweight planters, because they catch wind like sails. A broader base and a lower center of gravity matter more than raw weight alone.
You can also use a non-permanent anchoring system. If the planter sits beside a railing or column, a removable strap, turnbuckle, or heavy rubber base mat may add security without drilling into the building. Check local rules first, and never rely on a temporary strap as the only wind protection in exposed rooftop or coastal locations.
Place the planter in a wind-sheltered spot, group several planters together, and use low, dense plants or grasses rather than tall, sail-like shrubs. Keep drainage separate from the ballast chamber so the planter does not become waterlogged or unstable. Before planting, do a firm push test, and in very high-wind areas, ask a structural professional to confirm the setup. With ballast, paver weights, lockable casters, and smart placement, you get a planter that stays put when it needs to and can still be moved later.