Solid hotel wine list that earns its keep
Downtown · Winston Salem · Contemporary American · Visit Website ↗
Reviewed June 25, 2026
Wingman Metrics
Walking into Sir Winston, you get the sense that someone actually thought about the wine program — this isn't a hotel bar afterthought with four Cabs and a Pinot Grigio. The list is broad, international, and clearly meant to impress, which it mostly does. The room backs it up: polished and grown-up without being suffocating.
At an estimated 150-200 labels, the list covers a lot of ground — California dominates as you'd expect, but there's genuine range here with Spanish Garnacha Blanca and Tempranillo, an Argentine Malbec, German Riesling, New Zealand Sauvignon Blanc, and Sicilian Moscato rounding things out. The Opus One appearance signals they're aiming at serious wine drinkers, not just satisfying the table that orders whatever sounds familiar. That said, the depth is wider than it is deep — you won't find much in the way of grower Champagne, aged Burgundy, or serious Italian reds. The regional North Carolina angle in the food menu doesn't quite make it to the wine list, which is a missed opportunity given how the local wine scene has grown.
Twenty-plus options by the glass is genuinely generous, and the 6 oz versus 9 oz pour split gives you flexibility — ideal if you want to work through a few bottles' worth of variety across a meal. The glass list leans accessible: Meiomi Pinot Noir, Louis M. Martini Cab, Whispering Angel Rosé — crowd-pleasers, not barn-burners. Rotation appears limited; this feels like a list that gets revisited annually rather than seasonally.
Campo de Borja Garnacha Blanca — $10
Spain's Garnacha Blanca is chronically underrated and rarely this affordable at a hotel restaurant. It's textured, dry, and interesting — a steal compared to everything around it on this list.
J. Baumer Riesling (Rheinhessen)
Most tables at a place like this are going to reach for the Whispering Angel or something California. The Rheinhessen Riesling is the sleeper — dry, precise, and completely out of place in the best way on a list otherwise dominated by New World crowd-pleasers.
Meiomi Pinot Noir
Meiomi is fine, but it's a $14 retail bottle that earns restaurant markup fast. You can do better almost anywhere else on this list, and at these prices you're paying for the brand recognition more than the wine.
Matsu Tempranillo + Brussels Sprout Tacos
The earthy, slightly funky char on those Brussels sprout tacos wants something with grip and a little rusticity — the Matsu Tempranillo from Spain brings both without steamrolling the vegetable-forward dish.
✔️ The Bottom Line
Sir Winston is the rare hotel restaurant that makes a real effort on wine, and for Winston-Salem, that counts for a lot. Pricing runs steep enough that you'll feel it by the second bottle, but the selection earns at least one visit from anyone who takes wine seriously.
Reynolda / North Winston-Salem · Winston Salem · Upscale American
Graylyn Estate is a genuinely beautiful place to have dinner, but the wine list is an afterthought in a room that deserves intention. Order the sea bass, grab the La Crema, and try not to think too hard about what this list could have been.
Grocery Store
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Clemmons · Winston Salem · New American
Sixty Vines is a solid, reliable wine stop in Winston-Salem — the by-the-glass breadth is real and the staff knows their stuff, but the list reads like a greatest hits album rather than anything adventurous. Come for the volume, stay for the pizza, but don't expect to have your mind changed about wine.
Crowd Pleasers
Steep
Basic Stemmed
Knowledgeable & Friendly
Set & Forget
Proper
Downtown · Winston Salem · Indian
Oh' Calcutta's wine list is unremarkable on its own — but Tuesday nights flip the script entirely, and a $19 Pinot Noir with lamb vindaloo is a genuinely good time. Come for the food, plan around Tuesday, and don't overthink it.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Active Program
Acceptable
Downtown · Winston Salem · American
Cin Cin isn't a wine destination, and it doesn't pretend to be — but Wednesday half-price wine all day on bottles and glasses turns a generic list into a genuinely good deal with a burger in hand. Show up any other night of the week and order a beer.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Seasonal Rotation
Acceptable
Brookstown · Winston Salem · Italian
Quanto Basta punches above its weight for a mid-size Southern city Italian spot — the Italian-focused list is thoughtful, the prices are fair, and Thursday half-price bottles make it one of the best weekly wine deals in Winston-Salem. Come hungry, come on a Thursday, and order the Falanghina.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Seasonal Rotation
Acceptable
Silas Creek Pkwy · Winston Salem · Japanese / Sushi
Umi is a fun hibachi night out, and the wine pricing is honestly fairer than it has any right to be — but the list itself is an afterthought, and no amount of fair markup fixes a selection that's two bottles deep in personality. Order sake, or a cocktail, and come back to us when they add a Grüner Veltliner.
Grocery Store
Fair
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
· Atlanta · Contemporary American
By George is a fine place to drink wine if you know what you're walking into — a curated-but-safe list built for a stylish crowd that wants rosé and bubbles without friction. Come for the Crémant and the Tavel; don't expect to find anything that'll make you rethink your relationship with wine.
Plays It Safe
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
La Jolla · Chula Vista · Contemporary American
Nine-Ten is a genuinely good restaurant with a competent wine program — the sommelier is present, the list is legitimate, and the setting earns the price of admission. But the markups are aggressive enough that you'll want to be selective, because this list can eat your wallet if you reach for the obvious names.
Solid Range
Steep
Varietal Specific
Knowledgeable & Friendly
Set & Forget
Proper
Downtown LA · Los Angeles · Contemporary American
Otium is pulling serious wine weight for a restaurant most people visit for the food, and the combination of an eclectic 300-label list, knowledgeable staff, and a by-the-glass program with genuine personality earns it a Rager without hesitation. Send your wine-curious friends here — just tell them to actually read the list.
Deep & Eclectic
Fair
Varietal Specific
Knowledgeable & Friendly
Occasional
Proper
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