Wave erosion has moved coastal cliffs and bluffs landward over the centuries. Now climate change-induced sea-level rise (SLR) and the changes in wave action are accelerating coastline retreat around the world. Documenting the erosion of cliffed coasts and projecting the rate of coastline retreat under future SLR scenarios are more challenging than historical and future shoreline change studies along low-lying sandy beaches. The objective of this research was to study coastal erosion of the West Cliff Drive area in Santa Cruz along the Central California Coast and identify the challenges in coastline change analysis. We investigated the geological history, geomorphic differences, and documented cliff retreat to assess coastal erosion qualitatively. We also conducted a quantitative assessment of cliff retreat through extracting and analyzing the coastline position at three different times (1953, 1975, and 2018). The results showed that the total retreat of the West Cliff Drive coastline over 65 years ranges from 0.3 to 32 m, and the maximum cliff retreat rate was 0.5 m/year. Geometric errors, the complex profiles of coastal cliffs, and irregularities in the processes of coastal erosion, including the undercutting of the base of the cliff and formation of caves, were some of the identified challenges in documenting historical coastline retreat. These can each increase the uncertainty of calculated retreat rates. Reducing the uncertainties in retreat rates is an essential initial step in projecting cliff and bluff retreat under future SLR more accurately and in developing a practical adaptive management plan to cope with the impacts of coastline change along this highly populated edge.