California Royalty Anchored in the Chesapeake
Annapolis · Annapolis · Steak house · Visit Website ↗
Reviewed by the RagingWine Tasting Desk · April 7, 2026
RagingWine reviewed Lewnes' Steakhouse’s wine list and gave it The Rager — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
The wine list at Lewnes' arrives looking like a Greatest Hits of California Cabernet — Opus One, Shafer Hillside Select, Ridge Monte Bello — and it's immediately clear this kitchen takes its cellar as seriously as its dry-aged beef. A Best of Award of Excellence since 2004 isn't a fluke; this list has been tended to. The dark wood room and white tablecloths set the right stage for what's in your hands.
Three hundred to five hundred labels deep, and California is unambiguously the star — Stag's Leap, Jordan, Silver Oak, Paul Hobbs, Duckhorn, Far Niente. This is not a list trying to cover every corner of the wine world; it's a list that made a choice and committed hard to Napa and Sonoma. That focus works in a steakhouse context, though anyone hunting Burgundy or Barolo will need to dig. The ceiling is high — Shafer Hillside Select and Ridge Monte Bello signal serious intent — and the floor stays accessible with entry points in the $40-$60 range.
Fifteen to twenty-five by-the-glass options is genuinely solid for a room this focused, and the pours track the bottle list — expect California Chardonnay and Cabernet to dominate. Wednesday's half-price wine night is a legitimate reason to reroute your week and work through the glass program at a fraction of the cost. Rotation appears set rather than spontaneous, but the quality baseline is high enough that it rarely matters.
Jordan Cabernet Sauvignon 2019 — $145
Jordan is the reliable overachiever of Alexander Valley — classic structure, no pretension, and it holds its own against steaks twice the price. At $145 in a room where bottles top out near $600, this is where you put your money.
Ridge Monte Bello
Most tables here are ordering Caymus or Opus One on autopilot. Ridge Monte Bello is a Bordeaux-style Santa Cruz Mountains blend that routinely outperforms wines costing twice as much in blind tastings — and most diners walk right past it. Don't.
Opus One 2019
At $595 a bottle, you're paying a significant premium for the label in a restaurant setting. Opus One is a great wine — it's also widely available — and the markup here makes it a flex purchase more than a value decision. Spend that money on two bottles of something equally compelling.
Stag's Leap Wine Cellars Cabernet Sauvignon + Dry-aged New York strip steak
Stag's Leap built its reputation on structured, elegant Cab with enough dark fruit and iron-edged tannin to stand up to serious beef. A dry-aged strip has the intensity to match it without either side backing down. Classic call, still the right one.
Wednesday — Half-price wine night every Wednesday — applies to bottles and makes working through the glass program or mid-tier list a genuinely smart move.
The Bottom Line
Lewnes' is the kind of steakhouse wine list that actually earns its Best of Award of Excellence — deep California roots, serious ceiling bottles, and a Wednesday half-price night that's practically a civic service. The markups are steakhouse-steep across the board, but if you navigate smart, this is one of the better bottles-with-beef experiences on the mid-Atlantic coast.
Eastport · Annapolis · American pub fare
Davis' Pub is a great place to drink — just not wine. The list is inoffensive and priced fairly, but it exists as an afterthought in a place where the real action is cold drafts and steamed crabs. Order the Brancott if you must, then pivot to beer.
Grocery Store
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Spa Creek · Annapolis · Seafood / Steak
Chart House Annapolis is a reliable wine list in a genuinely great setting — you'll drink well enough, but you're paying for the view as much as the pour. Go in with eyes open on the markup and lean on the California stalwarts that earned their spots here.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Towne Centre Area · Annapolis · Wine Bar / Mediterranean
Smashing Grapes is quietly one of the better wine programs in the mid-Atlantic, operating in a market that doesn't always demand it — which makes it even more impressive. Send a friend here, absolutely, and tell them to skip the safe picks.
Deep & Eclectic
Fair
Varietal Specific
Knowledgeable & Friendly
Seasonal Rotation
Proper
Upper Main Street · Annapolis · Wine Bar / Bistro
Red Red Wine Bar is a genuinely fun, accessible spot if you go in knowing what it is: a bubbly-forward wine bar built for socializing and sharing flights, not deep-dive cellar exploration. Send your friend here for a casual night out — just don't send them expecting a sprawling wine list.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Church Circle · Annapolis · Tavern / Afternoon Tea
Reynolds Tavern is the kind of Wild Card that earns its badge by being completely sincere — a 275-year-old tavern that stocks Vieux Télégraphe and Maryland Albariño without making a big deal about it. If you're in Annapolis and skipping wine here in favor of a generic hotel bar down the street, that's on you.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Eastport · Annapolis · Seafood / Raw Bar
Blackwall Hitch isn't a wine destination, but it's a reliable spot to drink something decent without getting gouged — especially during happy hour. Send a friend here if they want a glass on the water, not if they're chasing something to talk about.
Crowd Pleasers
Fair
Basic Stemmed
Willing but Green
Active Program
Acceptable
Capitol Square · Madison · Steak house
Rare is a reliable wine destination for Napa devotees visiting Madison — the list is familiar by design, the WS Award of Excellence is well-earned, and the setting delivers. Just don't come here looking for natural wine or anything that strays from the California playbook.
Plays It Safe
Steep
Basic Stemmed
Willing but Green
Set & Forget
Proper
Brookfield · Brookfield · Steak house
Mr. B's is a reliable, well-kept steakhouse wine list that knows its audience and serves them well — just don't expect any surprises. If you're a California Cab loyalist heading out for a serious steak dinner in the Milwaukee suburbs, this is your spot.
Plays It Safe
Steep
Basic Stemmed
Willing but Green
Set & Forget
Proper
West Loop · Chicago · Steak house
BLVD Steakhouse doesn't reinvent the steakhouse wine list, but it executes the formula competently — solid producers, proper storage, and enough range to keep a table of Cab loyalists happy all night. Just go in with your eyes open on the markups and skip the trophy-bottle trap.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Proper
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