Dendritic core-double-shell architectures consisting of a hyperbranched polyglycerol core, a long aliphatic hydrophobic inner shell, and hyperbranched polyglycerol-based hydrophilic outer shell have been synthesized and characterized. They have been prepared from simple building blocks by applying,In anionic ring-opening polymerization protocol. The obtained, well-defined, globular, nanometer-sized architectures possess the ability to host polar and nonpolar guest molecules in water. The polymer-guest molecule complexes were characterized by UV and DLS measurements. Unimolecular transport behavior was observed for nonpolar guest molecules with transport capacities of 1.5 guest molecules per nanocarrier and particle sizes of 7-10 nm. However, for polar guest molecules, the formation of uniform aggregates with a diameter of 70 nm and transport capacities up to 10 guests per nanocarrier was detected.