Historical tropical cyclone (TC) and storm surge records are often too limited to quantify the risk to local populations. Paleohurricane sediment records uncover long‐term TC activity, but interpreting these records can be difficult and can introduce significant uncertainties. Here we compare and combine climatological‐hydrodynamic modeling (including a method to account for storm size uncertainty), historical observations, and paleohurricane records to investigate local surge risk, using Apalachee Bay in northwest Florida as an example. The modeling reveals relatively high risk, with 100 year, 500 year, and “worst case” surges estimated to be about 6.3 m, 8.3 m, and 11.3 m, respectively, at Bald Point (a paleorecord site) and about 7.4 m, 9.7 m, and 13.3 m, respectively, at St. Marks (the head of the Bay), supporting the inference from paleorecords that Apalachee Bay has frequently suffered severe inundation for thousands of years. Both the synthetic database and paleorecords contain a much higher frequency of extreme events than the historical record; the mean return period of surges greater than 5 m is about 40 years based on synthetic modeling and paleoreconstruction, whereas it is about 400 years based on historical storm analysis. Apalachee Bay surge risk is determined by storms of broad characteristics, varies spatially over the area, and is affected by coastally trapped Kelvin waves, all of which are important features to consider when accessing the risk and interpreting paleohurricane records. In particular, neglecting size uncertainty may induce great underestimation in surge risk, as the size distribution is positively skewed. While the most extreme surges were generated by the uppermost storm intensities, medium intensity storms (categories 1–3) can produce large to extreme surges, due to their larger inner core sizes. For Apalachee Bay, the storms that induced localized barrier breaching and limited sediment transport (overwash regime; surge between 3 and 5 m) are most likely to be category 2 or 3 storms, and the storms that inundated the entire barrier and deposited significantly more coarse materials (inundation regime; surge > 5 m) are most likely to be category 3 or 4 storms.