California Hits, Waterfront Views, No Surprises
Spa Creek · Annapolis · Seafood / Steak · Visit Website ↗
Reviewed by the RagingWine Tasting Desk · July 20, 2026
RagingWine reviewed Chart House’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
The wine list at Chart House Annapolis arrives looking confident — 150-plus bottles, recognizable names, and a California-forward lineup that makes sense when you're sitting on Spa Creek watching sailboats drift by. It's not trying to challenge you. It's trying to make sure you have a decent Chardonnay with your lobster, and largely it succeeds.
California dominates here, which is no surprise from a chain built on surf-and-turf comfort. You'll find the expected roster — Cakebread, Caymus, The Prisoner, Rodney Strong — and a nod to Pacific Northwest and France to round things out. The depth is real at 150-200 bottles, but it skews heavily toward crowd-pleasing labels you'd recognize from a grocery store end-cap. There's nothing adventurous here: no natural wine, no skin-contact curiosity, no deep Burgundy rabbit hole to fall down. What it does, it does reliably.
Twenty by-the-glass options is a generous pour for a chain, covering whites, reds, and presumably bubbles at $12-$20 a glass. The range tracks with the bottle list — expect California staples with consistent availability rather than a rotating creative program. Don't come here expecting the glass list to change with the seasons.
Rodney Strong Cabernet Sauvignon — $40 (estimated bottle)
Rodney Strong punches above its price point consistently, and in a list full of premium markups, it's likely one of the more honest bottles on the menu for what you're getting — solid Alexander Valley structure without the Caymus tax.
Cakebread Cellars Chardonnay
Cakebread gets written off as a predictable pick, but at a seafood-focused restaurant with lobster and Chilean sea bass on the menu, this is exactly the right call — restrained enough to not drown the fish, with enough weight to feel like an occasion.
Caymus Vineyards Cabernet Sauvignon
Caymus is fine wine — the problem is restaurant markup. At Chart House, you're almost certainly paying a significant premium over retail for a bottle that costs $80-$100 at any wine shop. Save it for home.
The Prisoner Wine Company Red Blend + Prime Rib
The Prisoner's dark fruit and vanilla-forward profile — big, ripe, a little indulgent — mirrors exactly what you want next to a slow-roasted prime rib. They're both unapologetically bold and neither is asking for your approval.
✔️ The Bottom Line
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.
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
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
Eastport · Annapolis · American Cafe
Eastport Kitchen isn't a wine destination, but it's also not pretending to be one — and for a casual neighborhood café in Annapolis, the wine program punches well above its weight class. The markups are mostly reasonable, the by-the-glass selection is genuinely broad, and if you know what to order, you can drink pretty well with your burger.
Crowd Pleasers
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
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