Chatham

Cuvée at Chatham Inn is a genuinely solid wine destination for the Cape — not trying to reinvent anything, but doing the classics well enough that you'll leave satisfied. If you're staying at the inn or dining here on a summer night, order the Gaja, get the Wagyu, and don't overthink it.

Stars is the real deal — a resort wine program with actual ambition, a sommelier who knows his list, and enough depth in California and Burgundy to reward guests who care. The markup stings and the list doesn't venture far from its comfort zone, but when the view is this good and the wine is this serious, it's hard to argue with the experience.