Natural convection heat transfer from a horizontal cylinder is of importance in a large number of applications. Although the topic has a rich history for unconfined cylinders, maximizing the free convective cooling through the introduction of sidewalls and creation of a chimney effect is considerably less studied. In this investigation, a numerical model of a heated horizontal cylinder confined between two vertical adiabatic walls is employed to evaluate the natural convective heat transfer. Two different treatments of the cylinder surface are investigated: constant temperature (isothermal) and constant surface heat flux (isoflux). To quantify the effect of wall distance on the effective heat transfer from the cylinder surface, 18 different confinement ratios are selected in varying increments from 1.125 to 18.0. All of these geometrical configurations are evaluated at seven distinct Rayleigh numbers ranging from 102 to 105. Maximum values of the surface-averaged Nusselt number are observed at an optimum confinement ratio for each analyzed Rayleigh number. Relative to the “pseudo-unconfined” cylinder at the largest confinement ratio, a 74.2% improvement in the heat transfer from an isothermal cylinder surface is observed at the optimum wall spacing for the highest analyzed Rayleigh number. An analogous improvement of 60.9% is determined for the same conditions with a constant heat flux surface. Several correlations are proposed to evaluate the optimal confinement ratio and the effective rate of heat transfer at that optimal confinement level for both thermal boundary conditions. One of the main application targets for this work is spent nuclear fuel, which after removal from the reactor core is placed in wet storage and then later transferred to cylindrical dry storage canisters. In light of enhanced safety, many are proposing to decrease the amount of time the fuel spends in wet storage conditions. The current study helps to establish a fundamental understanding of the buoyancy-induced flows around these dry cask storage canisters to address the anticipated needs from an accelerated fuel transfer program.