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Numerical simulations of boundary layer evolution in offshore flow of warm air over cool water are conducted and compared with aircraft observations of mean and turbulent fields made at Duck, North Carolina. Two models are used: a two-dimensional, high-resolution mesoscale model with a turbulent kinetic energy closure scheme, and a three-dimensional large-eddy simulation (LES) model that explicitly resolves the largest turbulent scales. Both models simulate general aspects of the decoupling of the weakly convective boundary layer from the surface, as it is advected offshore, and the formation of an internal boundary layer over the cool water. Two sets of experiments are performed, which indicate that complexities in upstream surface conditions play an important role in controlling the observed structure. The first (land–sea) experiments examine the transition from a rough surface having the same temperature as the ambient lower atmosphere, to a smooth ocean surface that is 5°C cooler. In the second (barrier island) experiment, a 4-km strip along the coastline having surface temperature 5°C warmer than the ambient atmosphere is introduced, to represent a narrow, heated barrier island present at the Duck site. In the land–sea case, it is found that the mesoscale model overpredicts turbulent intensity in the upper half of the boundary layer, forcing a deeper boundary layer. Both the mesoscale and LES models produce only a small change in the boundary layer shear and tend to decrease the momentum flux near the surface much more rapidly than the observations. Results from the barrier-island case are more in line with the observed momentum and turbulence structure, but still have a reduced momentum flux in the lower boundary layer in comparison with the observations. The authors find that turbulence in the LES model generated by convection over the heated land surface is stronger than in the mesoscale model, and tends to persist offshore for greater distances because of greater shear in the upper boundary layer winds. Analysis of the mesoscale model results suggests that better estimation of the mixing length could improve the turbulence closure in regions where the surface fluxes are changing rapidly. [ABSTRACT FROM AUTHOR]