Studying the biogeography and the phylogeography of the endemic Macaronesian red Festuca species (Loliinae, Poaceae) is of prime interest in understanding the speciation and colonization patterns of recently evolved groups in oceanic archipelagos. Coalescence-based analyses of plastid trnLF sequences were employed to estimate evolutionary parameters and to test different species-history scenarios that model the pattern of species divergence. Bayesian IM estimates of species divergence times suggested that ancestral lineages of diploid Macaronesian and Iberian red fescues could have diverged between 1.2 to 1.57 Ma. When empirical data was compared to the expected distributions of discordance and p-distance statistics, two species-history models were supported in which the first branching lineage derived in Canarian F. agustinii. Its sister lineage involved a recent polytomy, following the Canarian model, or the sequential branching of lineages leading to Madeiran F. jubata and finally to the sister clades of the continental F. rivularis and the Azorean F. francoi and F. petraea, following the Sequential model. Nested Clade Phylogeographic Analysis (NCPA) and a first-proposed host-parasite co-evolutionary ParaFit method were used to detect the phylogeographic signal. NCPA inferred long distance colonizations for the entire diploid red Festuca complex, but allopatric fragmentation and isolation by distance (IBD) patterns were inferred within archipelagos. In addition, the ParaFit method suggested a generalized pattern of a Stepping Stone Model at all hierarchical levels. Maximum likelihood - based Dispersal-Extinction-Colonization (DEC) models were superimposed on the Sequential species tree. The three-independent-colonization (3IC) model was the best supported biogeographic scenario, concurring with previous analysis based on multilocus AFLP data.