The discovery and characterization of extrasolar planets has been data-driven: clearly there are more things in heaven and earth than are dreamt of in our philosophies. As the demographics of the myriad diverse systems becomes known, we begin to piece together the larger story of their formation and evolution. Ultimately, we seek to understand the prospects for life elsewhere in the Universe. In addition to this scientific quest, 'exploration' also plays a role. In particular, the nearest star systems provide an opportunity to explore in detail strange new worlds. The recent announcement of a planet < 10 Mearth in the liquid-water zone of Proxima Centari sent shock waves through the community. What is the nature of this planetary system found in our own galactic backyard? Could it be habitable? How will we know and when? Here we will review recent progress in imaging planets from the ground, contributions the NASA/ESA/CSA James Webb Space Telescope will make in imaging sub-Saturns (perhaps with habitable moons) at larger orbital radii, and complementary work to be done by next generation Extremely Large Telescopes in thermal emission as well as NASA's WFIRST-AFTA in reflected light, which will enable us to image terrestrial planets around the nearest stars by the end of the next decade.