The first question you'll need to consider is a simple one: Are you looking for a canoe oar or a kayak paddle? Making the right choice will make your adventure all the more easy.
Then think about length. Wider vessels tend to require kayaks or oars with longer shafts—so you can reach the water without straining. Wide blades help you power your boat quickly and with efficiency, but often require more energy to maneuver.
Shorter-length shafts are better for boaters who make quick, rapid strokes in the water. Smaller paddles tend to translate less power, but they're easier to use if you're spending longer periods of time in the water.
Next, the shape of your shaft is key. Oars and paddles come with bent or straight shafts. What's the difference? Bent shafts position the blade for smooth, efficient strokes. Straight shafts are better for handling rocks and rapids in rough water.
Asymmetrical blades on your kayak tend to offer more control for aggressive paddlers, while symmetrical blades are preferred by those who prefer paddling at a slower pace.