We study the optimal strategy for a sailboat to reach an upwind island under the hypothesis that the wind direction fluctuates according to a Brownian motion and the wind speed is constant. The work is motivated by a concrete problem which typically arises during sailing regattas, namely finding the best tacking strategy to reach the upwind buoy as quickly as possible. We assume that there is no loss of time when tacking. We first guess an optimal strategy and then we establish its optimality by using the dynamic programming principle. The Hamilton Jacobi Bellmann equation obtained is a parabolic PDE with Neumann boundary conditions. Since it does not admit a closed form solution, the proof of optimality involves an intricate estimate of derivatives of the value function. We explicitly provide the asymptotic shape of the value function. In order to do so, we prove a result on large time behavior for solutions to time dependent parabolic PDE using a coupling argument. In particular, a boat far from the island approaches the island at $\frac{1}{2} + \frac{\sqrt{2}}{\pi} = 95.02\%$ of the boat's speed.