Here’s our list of favorite restaurants, we keep adding and subtracting. We listen closely to our guests as well as go by our own experience….In ALL cases, when you visit/make recommendations, tell them that the Flag House Inn recommended them, you might even get a surprise!    (OT= can make reservation on Open Table)  (CO = Carryout)

COVID – 19 update – most every place on this list is doing meal and nearly every restaurant in town has some form of outdoor dining

Fine Dining – reservations always recommended, we can assist

Carroll’s Creek – For over 30 years, great seafood, best view of Spa Creek/Harbor.  Both indoor and outdoor dining. Take the water taxi to the front door.  (Eastport) 410-263-8102 OT

O’Learys – Fantastic/Creative/Original seafood dishes with great service served in a venerable old house.  (Eastport) 410-263-0884 OT

Lewne’s Steakhouse – Since 1921, they’ve been serving prime steaks & chops with an extensive wine list.  Excellent service – Mack & Sam will take care of you! (Eastport) 410-263-1617 OT

Harry Browne’s – Quiet and scenic location on State Circle overlooking the State House. Great emphasis on fresh ingredients. More casual in upstairs bar.  410-263-4332  OT

Cafe Normandie – Fine French bistro on upper Main St. – extensive menu, expert preparation. All the classics. Great comfort food.  410-263-3382 OT

Osteria 177 – Fine Italian dining.  The veal chop is THE dish for that special event. 410-267-7700 OT

Reynolds Tavern – Historic setting in 1747 tavern – Known for afternoon tea, cellar bar and outdoor garden. Main room food good also! 410-295-9555 OT

Flamant – West Annapolis, less than 10 min drive.  Very foodie, super creative but small menu, great service 410-267-0274 OT

Severn Inn – Across Severn river bridge (450). Fine dining or informal bar. Lovely view across to Annapolis. 410-349-4000 OT

Blackwall Hitch – Extensive menu, big place/many group dinners.  Easy walk across bridge to Eastport. 410-263-3454 OT

Chart House – Lovely setting in former boat building factory. Take the water taxi to front door. Better for happy hour or drinks than dinner.  410-268-7166 OT

Ruth’s Chris – Steak Chain Eastport 410-990-0033 OT

Casual

Boatyard –  The “Margaritaville ” of Annapolis. Great seafood, reasonably priced, great boat drinks (cocktails), boating atmosphere, loud, fun.  Huge outdoor tent makes it an obvious choice. (Eastport). See this article – owner is great guy…  No reservations 410-216-6206

Iron Rooster – We aspire to make what they post on Instagram. Southern and breakfast all day. Fresh preparation.  Try the home made pop tarts! 410-990-1600 OT

Galway Bay – Our favorite place for a beer/cocktail. Pub/ friendly bartenders serve both the famous Irish brands and local craft beers. Great whiskey bar and the food is great!  Check schedule, frequent entertainment.  Locals spot. Maryland Ave. 410-263-8333 OT

Preserve – Farm to table, small plates, emphasis pickling/fermentation. Most foodie place downtown. Crispy kale! 443-598-6920

Officers Club – USNA (Lunch only M-F) – great food, lovely setting, reasonable prices. Pair with walking tour and USNA museum.

Vida Taco Bar – Pick your wrapping – lettuce, corn or flour and fill with 12 unique fillings. Great margaritas too! 443-837-6521

Vin 909 – Great foodie & pizza menu in neighborhood setting.  Gets VERY busy, no reservations (Eastport)   410-990-1846

Fox’s Den – Easy to miss along Main St, great cocktails, great pizza. Creative menu. No reservations. 443-808-8991

Forward Brewing – brand new micro brewery in Eastport, Great light food and the beer is very inventive… Neighborhood spot….

Dry 85/ Red Red Wine – Cocktail bar (D85) and wine bar (RRW). Light fare, flights.  443-214-5171 (D85)  410-990-1144 (RRW)

Dock St Pub – Top 5 in town for crab cakes, friendly bartenders, local-ish. 410-268-7278

Federal House – Big beer selection and extensive menu.  Big place but good service and big servings. Market Square 410-268-2576

Davis’ Pub – Far side of Eastport – if we lived in Eastport, we would be there regularly. Comfort food, pub fare, locals spot.  410-268-7432

Market House (Lunch/snack)- This is almost a category of it’s own, this is the re-re-renovated house at City Dock.  Many counter service options, gelato bar, raw bar, bakery.  Great views out to Ego Alley. 443-949-0024 CO

McGarvey’s – Raw bar, great pub fare, good for late night meal. Long time staple. 410-263-5700

Joss – great sushi & Asian dishes. Main St 410-263-4688. CO

Nano – Great sushi & Asian dishes as well. Both of these places are good.  410-267-6688  CO

Tarin Thai – Both the usual Pad Thai / curry but also many other options.  Dine in or carry out.  Dial up your own spice level! 138 Main St. 443-808-8553 CO

Middletown Tavern – Pub fare, upstairs piano bar, live music … been there forever in Market Square 410-263-3323

1771 Grill & Taproom – casual wood fired grill right on Market Square.  Nice outdoor seating.  410- 280-8686

Latitude 38 – great view of the harbor from the outdoor patio.  Great apps. 667 204 2282

O’Briens – Long time spot, outdoor dining 410-268-6288

Pusser’s (Waterfront Hotel) –  go for the daytime drinks & view  410-626-0004

West St – a category by itself – worth the walk, many great places

Level  – Small plates 410-268-0003 OT

Sailor Oyster Bar – Great happy hour prices, creative small plates. 410-571-5449

Lighthouse Bistro – What a great concept – Light House gives people with employment barriers the opportunity to learn while developing a resume and earning a living wage. And great food too!  410-424-0922 OT

Tsunami – Sushi & Asian 410-990-9868 CO OT

49 West Coffeehouse – See below – multi-purpose neighborhood spot 410-626-9796

Rams Head – Good bar food, obvious spot if heading to Ram’s Head Live.  Basement bar w/ live entertainment 410-268-4545 OT

Stan & Joe’s Saloon – Eclectic neighborhood bar.  Sports Bar. Big menu 410-263-1993

Metropolitan – Rooftop bar & brunch 410-280-5160 OT

Lemongrass – Thai 410-280-0086

El Toro Bravo – Mexican 410-267-5949

Luna Blu – Seafood/Italian 410-267-9950 OT

Worth the Drive (and it’s a short list!)

Cantler’s – Rated every year as one of the best crab houses in Maryland and for good reason. Nice waterfront location, extensive menu on addition to steamed crabs (crab soup & soft shell sliders are superb). No reservations. 10 min drive.  410-757-1311

Caliente (10-15 min) – Tremendous commitment to the community, great choice of Latin food (Mexican, Salvadoran, Columbian).  Pupusas, Chicken with mole, and much much more. (410) 626-1444  Call for reservations. CO

Jalepeno’s – (10-15 min) Tapas?  Yeah, got 60 choices. Spanish? Check  Cuban?  Of course.  Always rated top 5 in Annapolis and with good reason. Don’t be deceived by the average looking exterior. 410 266-7580

Kentmorr – 30 minute drive on Kent Island/Eastern Shore.  See our blog on this special place

Sandwiches

Bread & Butter Kitchen – Waterfront in Eastport, local and creative preparation. Tremendous commitment to the community.  Order online/phone, walk over, sit outside and enjoy the view 410-202-8680 CO

Pip’s Dock St Dogs – Best cheese steaks this side of Philly ..”Whiz Wit”! Awesome fries and great hot dogs. Locals fave for carry out lunch. CO

Big Cheese – Overstuffed sandwiches, snacks 410-263-6915 CO

Sofi’s Crepes – Breakfast, lunch or dinner. Mid favorite.  410-990-0929 CO

Chick & Ruth’s Deli – Long time spot, breakfast, famous name sandwiches, 830a pledge of allegiance  410-269-6737 CO

Mission BBQ – great support to armed forces and decent BBQ, dine in or CO

Jimmy John’s – We see their carryout guy many times a day to deliver to USNA. Must be good!  410-280-3561 CO

Potato Valley – Baked potatoes & sandwiches – State Circle 410-267-0902 CO

Coffee

Old Fox Books/ Brown Mustache Coffee – Very cool setting on Maryland Ave., Frequent live music, student hangout. Browse, surf or hang out  410-626-2020

Bitty & Beau’s – what a great story – great coffee and dedicated staff, run by people with intellectual and developmental disabilities. You will feel great all day having gone there.

49 West – Coffeehouse, Winebar, Jazz club, Dessert, light fare.  410-6269796

That Seattle Chain – Nice setting on Main St.

Ice Cream

There are 5 ice cream shops along Main St., we can highly recommend two of them:

Annapolis Ice Cream Company – Only shop that makes their own ice cream on site. Sources many other restaurants in town.  Look for the Penguins!

Red Bean – Take vanilla or chocolate base and add your own selection of flavorings.  Get ready to debate and defend your fave vs ours!