Valette Wines at The Matheson

Hazel Hill is legitimately one of the better resort wine programs in California wine country — deep list, proper staff, and a setting that earns the splurge. The markups are real and the vibe is unabashedly luxe, but if you're already in Healdsburg, this is worth the stop.

Jordan Estate is a polished, premium experience that knows exactly what it is — and if you're a Cabernet believer, it absolutely delivers. Just don't expect an adventure outside the estate's four corners, and come prepared for the price tag.

LIOCO is doing something genuinely uncommon in Healdsburg: making California wine that tastes curious instead of comfortable. If you're fatigued by the region's usual routine of ripe, oaky, and expensive, this is your detour.

Scout Field Bar is what happens when a luxury resort actually invests in its wine program instead of phoning it in — the list is deep, the producers are legit, and the setting makes everything taste better. Pricing is undeniably steep, but if you're already at Montage, you knew what you were signing up for.

BarnDiva is exactly what it looks like: a stylish, Sonoma-proud wine list that takes no risks and charges Healdsburg prices for the privilege. Send a friend here for a relaxed glass of something local — just tell them to skip the Cab.

Costeaux is the rare bakery where ordering a glass of wine at 11am feels like the correct decision. The list is small, locally rooted, and priced like they actually want you to order it — which, in Healdsburg, is not a given.