During the last decade, peptide radiopharmaceuticals have become an important class of tracers for the detection and localization of malignant neoplasms by peptide receptor imaging (PRI) and for therapeutic intervention by peptide receptor radiotherapy (PRRT). Various radiometalated peptides have entered detailed clinical studies or found broad application for peptide receptor radiotherapy. In contrast, radiohalogenated peptides could not benefit from this development. Especially with respect to the growing number of peptidic structures with high receptor affinity and the increasing demand for means of corresponding receptor status quantification for therapy planning and control, the development of methods for the improved availability of 18F-labeled peptides for positron emission tomography imaging is still a very important objective in radiopharmaceutical research. Consequently, as part of our ongoing efforts in this field, we investigated the potential of carbohydration as a valuable tool to modify pharmacokinetics of peptides and evaluated the influence of this modification on the in vitro and in vivo behavior of octreotide analogs. Furthermore, a new methodology is presented allowing for the fast and straightforward labeling of peptides in a chemoselective manner. This combined approach to the chemoselective conjugation of unprotected, carbohydrated peptides seems to have the potential for a redirection and reevaluation of the future of radiohalogenated peptides in nuclear medicine.