Cafe Figaro

Chianti Classico Riserva — $45

Chianti Classico Riserva is one of the most food-friendly wines on the planet and tends to carry fair markups at Italian spots that respect the region. At this price range, it's the kind of bottle that drinks well above its weight next to a plate of pasta.

Pinot Grigio delle Venezie

Most people gloss past Pinot Grigio on an Italian-heavy list, assuming it's filler. At a place with a proper wine program, though, a well-chosen Pinot Grigio delle Venezie can be a crisp, mineral-driven pour that actually competes with the room — especially if you're starting with something lighter before moving to the Barolo.

Sassicaia

Sassicaia is a genuinely great wine, but it's also one of the most widely distributed Super Tuscans in the world, which means restaurants can — and often do — charge a significant premium on name recognition alone. Unless you're celebrating something, the restaurant's other Tuscan options will drink nearly as well for considerably less.

Brunello di Montalcino + Osso buco

Osso buco needs a wine with structure, earthy depth, and enough acidity to cut through the richness of the braised veal shank. Brunello di Montalcino is basically built for this moment — the Sangiovese tannins and dried cherry fruit lock in with the savory braising liquid in a way that makes both the food and the wine better.