In the north Ionian, water circulation is characterized by a decadal alternation of cyclonic and anticyclonic regime driven by the mechanism called BiOS (bimodal oscillating system). The circulation regimes affect both vertical dynamics and the nutrient distribution. The north Ionian is then a good study area to investigate how changes in circulation can affect phytoplankton dynamics in oligotrophic regions. From in situ observations, for each circulation regime the averaged distribution of isopycnals is provided, and a depth difference of about 80m is estimated for the nitracline between the cyclonic and anticyclonic regime. Based on phytoplankton phenology metrics extracted from annual time series of satellite ocean color data for the period 1998–2012, the cyclonic and anticyclonic regimes are compared. Results show that the average chlorophyll in March, the date of bloom onset and the date of maximum chlorophyll were affected by circulation patterns in the north Ionian. In the center of the north Ionian gyre, the bloom started in December and chlorophyll was low in March when circulation was anticyclonic, whereas during the cyclonic circulation regime, a late chlorophyll peak, likely resulting from different phytoplankton dynamics, was commonly observed in March. An additional analysis shows that the winter buoyancy losses, which govern the mixed layer depth (MLD), also contribute to explaining the interannual variability in bloom onset and intensity. Two trophic regimes were then identified in the north Ionian gyre (NIG) and they could be explained with the relative position of the MLD and nitracline. The first one is characterized by an early winter bloom onset and the absence of a chlorophyll peak in March. It was observed when circulation was anticyclonic or when winter MLD was relatively shallow. Dominant regenerated production all year and an absence of significant nutrient supplies to surface waters are proposed to explain this trophic regime. Conversely, the second trophic regime is marked by a bloom onset in late winter (i.e., February) and a chlorophyll peak in March. The chlorophyll increase was interpreted as a direct response to the nutrient enrichment of surface waters. This winter–spring bloom was observed when circulation was cyclonic and when winter mixing was relatively strong.