The first four members of a new family of C_3v-symmetrical “two-story” calix[6]aza-crypands have been synthesized. These large funnel shaped aza-ligands are formed through introduction of three aromatic arms as spacers onto the small rim of a calix[6]arene, and subsequently capped with the tripodal aza caps tacn [1,3,5-triazacyclononane] or tren [tris(aminoethyl)amine]. A key feature for an efficient final 1:1 macrocyclization appears to be an adequate geometrical fit between the extended calixarene scaffold and the aza caps.