Don Cheech Restaurant

Chianti Classico Riserva — $45

Chianti Classico Riserva at the lower end of this list's range is almost always a win with Italian food — structured enough to handle red sauce, approachable enough to not need a lecture. At Don Cheech's price point, it's the bottle that earns its keep.

Pinot Grigio (Alto Adige)

Most people walk past Alto Adige Pinot Grigio without a second look because they're thinking of the flat, forgettable stuff. Up in the Alto Adige, the grape actually has spine — minerally, crisp, with real presence. Order it while everyone else argues over the Barolo.

Sassicaia

Sassicaia is a legitimate wine, no argument there — but it's also one of the most universally distributed bottles in the world, and restaurant markups on trophy Super Tuscans can be punishing. Unless someone else is paying, you'll get more pleasure per dollar elsewhere on this list.

Brunello di Montalcino + Linguine Vongola

Hear us out — Brunello is usually a red meat call, but a well-aged one with some secondary savory character against briny clam pasta is a genuinely interesting move. The wine's earthy depth doesn't fight the seafood; it frames it.