24 Perfect Romantic Restaurants in Annapolis, Maryland

© Vin 909

Vin 909 is a wine bar and restaurant that serves fantastic farm-to-table New American cuisine. You can’t go wrong with delicious, passionately prepared dishes, such as the Clams & Butternut Squash Curry, Seared Monkfish (in a bacon, mango, and habanero reduction), or the Italian Boar Sandwich.

Or try one of their extremely popular brick-oven pizzas like the Pinnapolis. Hospitality expert Alex Manfredonia and Executive Chef Justin Moore are the owners of Vin 909. You will love the ever-changing, seasonal menu at this charming eatery, situated in a classic Sears Roebuck house in the eclectic Eastport neighborhood of Annapolis.

909 Bay Ridge Avenue, Annapolis, MD 21403, 410-990-1846

© Boatyard Bar & Grill

For some of the freshest local seafood and regional classics, you will want to check out Annapolis’s tasty Boatyard Bar & Grill. Dive into to their delicious, signature dishes such as Antione’s Stuffed Oysters, Cream of Crab Soup, Finley’s Fantabulous Fish Tacos, or “The Best Crab Sandwich You’ll Ever Eat.” Wash it all down with an ice-cold beer.

Owner Dick Franyo opened Boatyard Bar & Grill in 2001 after retiring from his thriving, 30-year business career. A favorite of local sailors, fishermen, and Chesapeake enthusiasts, this friendly eatery is located on Restaurant Row in Annapolis’s historic maritime district of Eastport.

400 Fourth Street, Annapolis, MD 21403, 410-216-6206

© Iron Rooster

The popular Iron Rooster restaurant serves a new twist on traditional Southern comfort foods for breakfast (available all day), lunch, supper, or drinks. Treat yourself to scrumptious grub such as the Smoked Brisket Benedict, Chicken & Waffles, Bacon & Egg Ramen (with sliced pork belly), or the Dixie Pot Roast.

Wash it all down with a refreshing selection or signature cocktail from the bar such as the Cock-A-Doodle-Doo. Hospitality expert Kyle Algaze first opened Iron Rooster in 2014, pouring all of his passion into the restaurant. Enjoy views of Ego Alley at this outstanding eatery located on downtown Annapolis’s City Dock.

12 Market Space, Annapolis, MD 21401, 410-990-1600

© Carpaccio Tuscan Kitchen and Wine Bar

Carpaccio Tuscan Kitchen and Wine Bar is a sophisticated upscale Italian restaurant in Annapolis' vibrant downtown district, originally opened in 2008 as part of the MONTE restaurant group. The charming restaurant serves up a full menu of authentic Tuscan specialties, including high-quality brick-oven pizzas in flavors ranging from traditional margherita to meat lovers' pizzas prepared with pepperoni, ham, sausage, and bacon. Refined land and sea entree options include seafood fettuccine Mediterraneo, chicken scarpariello, veal porcini, and linguine alle vongole, served up with elegant sides such as roasted brussels sprouts and sauteed broccolini. Fine Italian-style pasta options include pappardelle bolognese, fettuccine carbonara, and penne pasticcio. A full wine bar offers high-quality imported selections, with discounted pricing offered at happy hour.

1 Park Pl, Annapolis, MD 21401, Phone: 410-268-6569

© Galway Bay Irish Pub

Galway Bay Irish Pub is a convivial place where you can eat and drink merrily, enjoying their menu options of Gaelic grub and American standards. You can’t go wrong with delicious Irish Classics like Oysters O’Leary, Shepherd’s Pie, Corned Beef & Cabbage, or Murphy’s Roast. Many gluten-free options are also available.

Save room for a spectacular dessert like their Irish Egg Nog Spiced Pumpkin Pie! Friends Anthony Clarke and Michael Galoway first opened Galway Bay Irish Pub in 1998. You will find this charming eatery in a beautiful historic building downtown, situated very close to the Naval Academy.

63 Maryland Avenue, Annapolis, MD 21401, 410-263-8333

© Mason’s Famous Lobster Rolls

If you’re in the mood for lobster, you simply must visit the quaint yet incredible Mason’s Famous Lobster Rolls. Whether you order the Lobstah BLT, Connecticut Roll, Lobstah Bisque, or the Maine Lobster Salad Roll, your taste buds are sure to thank you! All of Mason’s lobsters are directly from Maine after being exclusively caught by a small fleet of ships.

Restaurateur Dan Beck and his wife open this charming eatery, which has been open since 2015. They named the place after their son. Enjoy the friendly atmosphere at Mason’s Famous Lobster Rolls, located across the street from the Maryland State House.

180 Main Street, Annapolis, MD 21401, 410-280-2254

© Jimmy Cantler’s Riverside Inn

Maryland’s iconic, waterfront Jimmy Cantler’s Riverside Inn serves incredible, fresh seafood, and they specialize in crabs. Savor delicious, passionately prepared dishes such as Jimmy’s Steamed Snow Crab, Spicy Oyster Po’Boy, Crab Mac ‘N Cheese, or the breaded Clam Strips. You simply can’t leave until you try their famous Maryland blue crabs.

Former Chesapeake Bay waterman Jimmy Cantler opened this renowned restaurant in 1974 with the help of his lovely wife Linda. Grab yourself a little slice of heaven in the form of some amazing seafood at Jimmy Cantler’s Riverside Inn, located in Mill Creek – just minutes from the Annapolis City Dock.

458 Forest Beach Road, Annapolis, MD 21409, 410-757-1311

© Baroak Cookhouse & Taproom

Baroak Cookhouse & Taproom is a popular and casual neighborhood restaurant that specializes in spectacular Belgian-American cuisine. You can’t go wrong with unbelievably tasty dishes like Mussels a la Mariniere, Bison Chili, Eggplant Lasagna, or their famous Moules Frites.

Or stop in for brunch and try the Ribeye Hash! Wash it all down with something from their inspired selection of international and local craft beers. Thriving restaurateur and beer aficionado Chef Teddy Folkman opened Baroak Cookhouse & Taproom in 2015, which is his first venture in Annapolis. You will find this charming eatery inside the Loews Annapolis Hotel close to the Naval Academy.

126 West Street, Annapolis, MD 21401, 410-295-3225

© Red Red Wine Bar

Red Red Wine Ba doesn’t only offer a great wine program, but they also serve delicious New American cuisine. Savor incredible, boldly flavored dishes like Bacon-Wrapped Stuffed Shrimp, Manchego Chicken Panini, Braised Lamb Shank, or Maryland Crab Soup.

Or stop in for the New Orleans Sunday Brunch & Champagne Bar and try the Shrimp Creole Omelette. Restaurateur power couple Brian (a former DC news anchor) and Lisa Bolter are the owners of Red Red Wine Bar, which has been open since 2011. Come for the wine and stay for the food at this hip hangout located across the street from the Maryland State House.

189B Main Street, Annapolis, MD 21401, 410-990-1144

© Miss Shirley’s

Miss Shirley’s Cafe serves delicious American classics with Southern influences. Dive into tasty dishes like Fried Green Tomatoes, S’mores Baked Banana Skillet, Down on the Bayou Benedict, or Bubba’s Slider Trio.

Delicious craft cocktails are also available. Baltimore native Eddie Dopkin opened the original Miss Shirley’s in Baltimore in 2005. He named it after an amazing cook, Miss Shirley Mc Dowell, a staple in the Baltimore culinary community. You will find this upscale-casual eatery nestled between College Creek and Old Woman’s Cove.

1 Park Place, Annapolis, MD 21401, 410-268-5171

© Lemongrass

Lemongrass restaurant serves modern Thai cuisine. Enjoy the electric atmosphere, as you treat yourself to tasty, boldly flavored dishes, such as the Duck Curry, Pad Pik Khing Spicy Eggplant, or the Spice-Ghetti Mahi Mahi.

Vegetarian options are also available. Lemongrass, owned by entrepreneurial and visionary restaurateur owners Gavin Buckley and Jody Danek (and their wives, Julie and Kristen) and Stanley Hsu, has been open since 2005. You will find this popular eatery in a little yellow house, nestled between the Naval Academy and Old Woman’s Cove.

167 West Street, Annapolis, MD 21401, 410-280-0086

© Carrol’s Creek Cafe

Enjoy a fabulous waterfront dining experience overlooking Spa Creek at the upscale Carrol’s Creek Cafe, which serves incredible seafood and classic Chesapeake fare. Savor unbelievable, expertly prepared dishes such as the Pepper Crusted Beef Tenderloin Carpaccio, Lobster & Black Truffle Pot Pie, or Seasonal Vegetable & Mushroom Risotto.

Or pop in for breakfast and try the Tortilla Casserole! They also have a splendid wine program with plenty of options to accompany your meal. The iconic Carrol’s Creek Café has been open since 1983 and is owned and run by Jeffrey Jacobs and his beautiful family. You will find this classy restaurant in Annapolis’s Eastport neighborhood.

410 Severn Avenue, Annapolis, MD 21403, 410-263-8102

© Jalapeno’s

If you’re in the mood for something fun and exotic, try Jalapeno’s Restaurant, which serves fantastic, authentic Spanish and Mexican cuisine. Dive into tasty, boldly flavored dishes such as the Hongo a la Parilla Tacos, Chuleta de Cerdo, Paella Valenciana, or Pesto Quesadilla.

Try the delicious sangria or another selection from the full bar to quench your thirst. Mexico native Alberto Serrano and Spain native Gonzalo Frenandez opened Jalapeno’s together in 1999. They’ve brought in Executive Chef Obed Serrano to take charge of the culinary creations. You will find this spicy eatery at the Annapolis Towne Center.

85 Forest Drive, Annapolis, MD 21401, 410-266-7580

© Osteria 177

Enjoy a beautiful, intimate night at Annapolis’s elegant and renowned Osteria 177, which specializes in Italian coastal cuisine and spectacular wine. Savor unbelievable, passionately prepared dishes like Penne Con Polpa di Granchio e Arugola, Scampi alla Pescarese, Pollo al Marsala, or a Gypsy Chicken Panini.

Be sure to try something delicious from their extraordinary wine list! The Italian-born owner and chef Arturo Ottaviano first opened Osteria 177 in 2006, and it has since become a local favorite thanks to his tasty culinary creations. This sophisticated restaurant is located downtown close to Maryland State House and the Naval Academy. Things to Do in Annapolis, Places to Visit in Maryland

177 Main Street, Annapolis, MD 21401, 410-267-7700

© Sin Fronteras Cafe

Sin Fronteras Cafe serves excellent Mexican and Latin cuisine with a Miami flare. Treat yourself to extraordinary, boldly flavored dishes like the Peruvian Lomo Saltado, Margarita Salmon, Pork Chop a la Mamajuana, or Chicharron en Salsa Verde.

Be sure to try one of their signature margaritas – they’re said to be the best in town! Restaurateur friends Walter Vasquez and Wilmer Romero opened Sin Fronteras in 2014. Enjoy the fun and friendly atmosphere at this spectacular restaurant located close to the Annapolis Towne Center.

2129 Forest Drive, Annapolis, MD 21401, 410-266-0013

© Dry 85

Dry 85 restaurant specializes in extraordinary drinks and delicious, modern twists on American comfort food. Treat yourself to amazing dishes like the Blue Cheese and Fig Burger, Fried Oyster Po Boy Sliders, or Slow-Roasted Pork Ribs with Housemade Blueberry Sauce. Wash it all down with a fine bourbon or a refreshing craft beer.

Stop in for brunch and try the Hogs ‘n Hops! News anchor-turned-restaurateur Brian Bolter and his wife Lisa opened Dry 85 in 2014. The restaurant is modeled after a Prohibition-era speakeasy, and you will find this fine establishment in a back alley garage near State Circle and the Naval Academy.

193B Main Street, Annapolis, MD 21401, 443-214-5171

© Cafe Normandie

Café Normandie specializes in phenomenal French Country Cuisine with Maryland seafood specialties. Savor unbelievable and passionately prepared dishes such as the Apple Cheddar Crepe, Salmon with Blueberries, or Angus Steak with Bordelaise Sauce. Or stop in for breakfast and try the tasty Eggs Florentine.

Everything is made from locally sourced, sustainable ingredients, meaning you can enjoy your meal and support the community at the same time. An impressive wine list is also available. Best Chefs America Award-winning Chef Jean Louis Evennou (a native of France) first opened Café Normandie in 1986. He pours his heart into every dish he makes. Enjoy the cozy atmosphere at this charming eatery located in the heart of downtown Annapolis.

185 Main Street, Annapolis, MD 21401, 410-263-3382

© O’Leary’s Seafood

O’Leary’s Seafood serves some of the best seafood the city has to offer – it is freshly caught and prepared to perfection. You can’t go wrong with incredible, expertly prepared dishes such as Bronzino Tripoli, Jamaican Salmon, Pork Frites, or Sopa de Mariscos. Or stop in for brunch and try the Blue Ridge Benny.

Choose something cold and refreshing from the tempting wine and cocktail program to complete your meal. Owner Wil Peterson first opened O’Leary's Seafood in 1983, and it has since become a popular local eatery. You will find it in a charming old house near Horn Point.

310 Third Street, Annapolis, MD 21403, 410-263-0884

© Federal House Bar & Grille

Annapolis’s landmark Federal House Bar & Grille serves up incredible, award-winning New American cuisine. Savor delicious, expertly prepared dishes like their famous Cream of Crab Soup, Baked Stuffed Flounder, Chicken Diablo, or Guinness Braised Pot Roast. In addition to a nice wine list, they also have 25 beers on tap, a full bar, and occasional live music and DJs.

Bring Fido with you to enjoy a nice meal on the pet-friendly patio – they even have a Doggie Menu! This iconic restaurant is located inside the Federal House, established in 1830. You will find it on Market Space in the Annapolis Harbor.

22 Market Place, Annapolis, MD 21401, 410-268-2576

© Davis’s Pub

Davis' Pub is a popular hangout that serves creative pub fare and has been featured on The Food Network’s “Diners, Drive-Ins, and Dives” with Guy Fieri. Treat yourself to fantastic foods like the Crab Cake Sandwich, Pulled Pork Barbeque Sandwich, Chesapeake Bay Retriever Sandwich, or Chicken Tostadas.

Don’t miss the Fried Pickles! Wash it all down with a refreshing draft beer. Originally founded as a general store in the 1920s (and later a lounge in the 1940s), it later became Davis’s Pub in the 1980s. Today, Lee and Michaela Troutman are the happy owners of the pub, which you will find in the Eastport community.

400 Chester Avenue, Annapolis, MD 21403, 410-268-7432

© McGarvey’s Saloon & Oyster Bar

For the best night out, you will want to check out Annapolis’s popular McGarvey's Saloon & Oyster Bar, which serves scrumptious pub fare in addition to selections from its raw bar menu. Start your meal off with the Crab Balls appetizer before diving into incredible dishes like Sesame Seed Fried Flounder, Fresh New England Sea Scallop, or a Bacon & French Roquefort Burger.

Grab a refreshing craft beer and enjoy the live music (every Friday and Saturday night). Local hero Mike Ashford first opened McGarvey’s in 1975. Check out this hip hangout downtown, very close to the Annapolis City Dock.

8 Market Space, Annapolis, MD 21401, 410-263-5700

© Royal Karma

Royal Karma restaurant specializes in North Indian cuisine. Savor extraordinary flavors in amazing dishes such as the Malai Kofta, Chicken Mazedar, Lamb Seekh Kabob, or Salmon Tikka Masala. Save room for tasty dessert like Gulab Jamun. Enjoy the intimate setting at Royal Karma restaurant, located at Technology Park in Technology Park.

302 Harry S. Truman Parkway, Suite K, Annapolis, MD 21401, 410-266-5006

© Chick and Ruth’s

Chick and Ruth’s Delly serves incredible sandwiches, old-fashioned milkshakes, ice cream, and baked goods. Get your grub on with delicious treats like the Super Duper Colossal three-pound burger, Corned Beef Sandwich, or the Jumbo Lump Crab Cake Wrap.

Or stop in early and try the Homemade Sausage Biscuits & Gravy. Open for decades, the Delly was originally founded by Chick and Ruth Levitt and sits in a historic building that also houses the owners’ Scotlauer Inn Bed & Breakfast. You will find Chick and Ruth’s downtown close to the Maryland State House.

165 Main Street, Annapolis, MD 21401, 410-269-6737

© Joss Cafe & Sushi Bar

The popular Joss Café and Sushi Bar offers incredible Japanese eats. Savor a tasty selection from the sushi bar such as the Maguro Poke or the Mediterranean Sashimi.

Or try something from their other menu like Chili Scallop Wontons or Pan Fried Dumplings. Joss Café and Sushi Bar has been open since 1991. Enjoy this warm and friendly eatery located right across the street from the Maryland State House and State Circle.

195 Main Street, Annapolis, MD 21401, 410-263-4688