Drainage for wood deck planters
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Perhaps when you have decided on where you want your planters and before you put in soil you could drill drainage hole through the pots and the step at the same time so they water could flow straight through to the ground. I would seal the holes that are on the steps to prevent water seeping into the wood from the raw cut. Make small marks to mark the perimeter where the pot will be before you move it to seal the holes. You can do this, it will look gorgeous if it is anything like the pictures you have above. I do this to the roller bases that I buy or make to put my large pots on so they can drain and not hold water like they do when you purchase or make your own and the pots can't drain because the water stays on the platforms because of the elevated sides.
We have this same problem on our deck. We found extra large plates or terra cotta water catches to put under each plant. You can purchase the terra cotta in many sizes. To save water, we also placed smaller plants above the larger plants so the overflow water would be caught by the larger plant under neath.
Do the pinterest pics you posted come with tutorials? They might tell you how they did what is in the picture. This article addresses the issue of drainage:
http://www.diynetwork.com/how-to/outdoors/patios-and-decks/design-ideas-for-deck-planter-boxes
I agree that drilling a drainage hole would be beneficial; however, I would first line your planter with a heavy duty plastic liner (garbage sack, for example, if on budget). I would make a hole in the liner, as well, which lines up with the hole made in the planter. Then I would take a hose (old piece of garden hose or fountain hose segment) and thread the hose through both the planter box and liner. Finally, attach and seal the hose with water resistant tape (or silicone if using a liner that isn't flexible like a garbage bag). In a nutshell, the liner protects your lovely planter from plant and water decay while the hose provides drainage out of planter and away from your super nice deck (which could be directed towards other planted areas alongside your deck - water once and give two areas a drink:) This idea is also portable. Good Luck!
Build whatever style you wish. For the drain holes, I would drill holes and that line up with the slats in your deck and install funnels or plastic tubing to fit between the deck slats and drain to the area below.
Use aluminium sighting for a ru off. They say that drained water is the best for other plants.