Wednesday Nights Just Got a Lot Cheaper
West Annapolis · Annapolis · Greek and American, Steakhouse
Reviewed by the RagingWine Tasting Desk · July 20, 2026
RagingWine reviewed Paul's Homewood Cafe’s wine list and gave it The Reliable — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
Paul's Homewood Cafe hands you a short, unpretentious wine list that matches the room — warm, casual, zero fuss. Don't come here expecting an esoteric deep-dive; do come here expecting honest pours at prices that don't make you wince. The California-Greece-Italy trifecta is exactly what you'd predict for a neighborhood spot doing moussaka and steaks side by side.
The list clocks in at somewhere between 20 and 35 bottles, leaning hard on approachable crowd-pleasers: Kendall-Jackson, Robert Mondavi Private Selection, Kim Crawford, Santa Margherita. There's a nod to Greek wine in the mix, which makes sense given the menu and gives the list a small personality boost above pure grocery-store territory. Don't expect any surprises from Burgundy or the Rhône, and there's no sign of anything natural or esoteric. What's here is competent and chosen for ease — nothing that will excite a wine nerd, but nothing that will embarrass the table either.
Six to ten options by the glass covers the basics: a Chardonnay, a Cab, a Pinot Grigio or two, a Sauvignon Blanc, and a Prosecco to start. Rotation isn't something Paul's appears to sweat over — this reads as a set-and-hold program rather than something that changes with the seasons. That said, the glass prices are genuinely fair for a sit-down restaurant in Annapolis, which is more than you can say for a lot of spots in this zip code.
Santa Margherita Pinot Grigio Alto Adige — $11/glass
At $11 a glass, this is the sharpest pour on the list. Santa Margherita retails around $23 a bottle, so you're getting a clean, food-friendly Alto Adige Pinot Grigio at a markup that barely registers. Order two.
Ruffino Prosecco DOC
Most people skip the bubbles at a Greek-American steakhouse, but at $9 a glass the Ruffino Prosecco is an easy aperitivo that works surprisingly well against the briny, herb-forward flavors coming out of the kitchen. It's an overlooked opener.
Robert Mondavi Private Selection Cabernet Sauvignon
Eight dollars a glass sounds fine until you remember this is a $11 bottle at any grocery store. It's not bad wine, but there's no reason to order it when better value is sitting right next to it on the list.
Kim Crawford Sauvignon Blanc Marlborough + Crab Cakes
The Kim Crawford's citrus snap and grassy edge cut right through the richness of a good crab cake. It's a classic pairing logic — bright acid against sweet shellfish — and at $10 a glass it won't break the bank while you're doing it.
Wednesday — Half-price bottles on Wednesdays; all bottles reportedly included up to at least $100, though an explicit price cap has not been confirmed. One of the better midweek wine deals in Annapolis.
✔️ The Bottom Line
Paul's isn't a wine destination, but it's also not trying to be — and the Wednesday half-price bottle program turns a reliable neighborhood dinner into a genuinely smart night out. Bring someone you like, order the moussaka, and let Wednesday do the work.
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
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