Transitional disks are objects whose inner disk regions have undergone substantial clearing. The Spitzer Space Telescope produced detailed spectral energy distributions (SEDs) of transitional disks that allowed us to infer their radial dust disk structure in some detail, revealing the diversity of this class of disks. The growing sample of transitional disks also opened up the possibility of demographic studies, which provided unique insights. There now exist (sub)millimeter and infrared images that confirm the presence of large clearings of dust in transitional disks. In addition, protoplanet candidates have been detected within some of these clearings. Transitional disks are thought to be a strong link to planet formation around young stars and are a key area to study if further progress is to be made on understanding the initial stages of planet formation. Here we provide a review and synthesis of transitional disk observations to date with the aim of providing timely direction to the field, which is about to undergo its next burst of growth as ALMA reaches its full potential. We discuss what we have learned about transitional disks from SEDs, color-color diagrams, and imaging in the (sub)mm and infrared. We then distill the observations into constraints for the main disk clearing mechanisms proposed to date (i.e., photoevaporation, grain growth, and companions) and explore how the expected observational signatures from these mechanisms, particularly planet-induced disk clearing, compare to actual observations. Lastly, we discuss future avenues of inquiry to be pursued with ALMA, JWST, and next generation of ground-based telescopes.