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Lovely Dining Spots for Your Valentine’s Day

Feb 12, 2015 02:45PM ● By Melissa Lauren
by: Melissa Lauren

Romantic, fun, playful, adventurous, colorful, sophisticated – those may all be words that describe your valentine this year but these words can also be used to describe lovely dining spots for your Valentine’s Day. I have organized a wide variety of restaurants to satisfy every taste at every budget with every type of ambiance imaginable. I’m sure you’ll love your Valentine’s experience at any of these restaurants! Don’t forget that all of these spots require reservations. Have fun and Happy Valentine’s Day from What’s Up? Media!

“In love, one and one are one.” ― Jean Paul Sartre

Fun Factoid: Valentine greetings were popular as far back as the Middle Ages, though written Valentine’s didn’t begin to appear until after 1400. The oldest known valentine still in existence today was a poem written in 1415 by Charles, Duke of Orleans, to his wife while he was imprisoned in the Tower of London following his capture at the Battle of Agincourt. Several years later, it is believed that King Henry V hired a writer named John Lydgate to compose a valentine note to Catherine of Valois.



Now that we’ve enjoyed some history on the holiday as an appetizer, let’s dig in to those Valentine’s Day dining spots…

Downtown Annapolis

Osteria 177 – Italian’s are known for their passion and the authentic Northern Italian cuisine at Osteria is perfetto! The ambiance is supremely romantic, plus with their extensive wine list, what’s not to love? For more information visit

Red Red Wine Bar – The locals love this place for good reason. The staff is friendly and the atmosphere is fun. At Red Red Wine Bar, they proudly proclaim that they are not wine snobs. They simply love sharing the magic in each unique bottle. For more information visit

Upper Annapolis

Miss Shirley’s Café – For those who love brunch more than dinner, Miss Shirley’s Café rightly begs the question, “Why should dinner have all the fun?” This month, Miss Shirley’s is featuring Sweet and Savory Pancakes, French Toasts, and Omelets that are sure to please. For more information visit

Level, A Small Plates Lounge – Level’s menu features local, sustainable ingredients. Share the love and share your plates. It is fun to order several different items and try a little bit of everything. And, their cocktails are fantastic! For more information visit

Eastport/Bay Ridge

The Main Ingredient – If you love dessert, The Main Ingredient is your dessert destination. This spot is wonderful for brunch, lunch, and dinner where they serve meals that make life delicious. Although, their desserts are divine, much better than a box of chocolates! For more information visit

Lewnes’ Steakhouse – At Lewnes’ you’ll enjoy fine dining with U.S. Prime Steaks and sophisticated wines as you sit in comfy leather booths with romantic lighting. For more information visit

Carrol’s Creek Café – Is an elegant waterfront seafood restaurant overlooking Spa Creek and serving classic Chesapeake fare making it a wonderful spot for brunch, lunch, and dinner. The food is as enjoyable as the view! For more information visit

Ruth’s Chris Steakhouse – At Ruth’s Chris Steakhouse you’ll enjoy seafood that is just as good as the steak. The environment will strike your fancy without being stuffy. Here, they are serious about making sure you have a good time. For more information visit

Boatyard Bar and Grill – Boatyard Bar and Grill is the quintessential boaters and sailors restaurant. This family-friendly restaurant is casual and cool. They have great brunch, lunch, and dinner menus; any of their meals will make your kids say, “Yum!” And for adults, the dinner specials and the bloody mary’s at brunch are always winning. For more information visit

Greater Annapolis

The Point Crab House and Grill (Arnold) – This casual waterfront eatery offers American fare with Maryland Chesapeake specialties. At The Point Crab House they serve up quite possibly the largest Crab Cake in town. For more information visit

Gordon Biersch (Parole) – This German-style pub menu serves authentic lagers and hand-crafted meals you’ll love. They even have a late night menu. For more information visit

Jalapenos (Parole) – You may already love their famous happy hour but wait until you try their Sangrias and Margaritas on a nice Valentine’s dinner date. Jalapenos serves up authentic Spanish and Mexican cuisine. For more information visit

Cantler’s Riverside Inn (Mill Creek) – A Chesapeake Tradition, Cantler’s is a classic Maryland Crab House perfect for the whole family. This spot will make any seafood lover happy on Valentine’s Day! For more information visit

West County

Blue Dolphin Seafood Bar & Grill (Crofton) – Seafood and Sushi and Specials, oh my! This spot is casual and fun and to top it all off has over 50 labels of wine. For more information visit

Rip’s Country Inn (Bowie) – Valentine’s Specials include Stuffed Lobster Tail, Stuffed Rockfish, and New York Strip just to name a few. This restaurant is unique in décor, remembering the days when Bowie was central to the horse racing circuit. Booths look like horse stalls and the exterior resembles a barn. For more information visit


Broadneck Grill and Cantina – This dining spot specializes in contemporary American and Mexican cuisine in a family-friendly atmosphere. They have Margaritas, homemade Sangria, and award-winning desserts. Your whole family is sure to love their dining experience. For more information visit

Old Stein Inn – The Old Stein Inn is truly authentic, serving delicious German fare including various types of Schnitzel, Elk Sausage, and delicious Munster Cheese Crab Soup. Pair any delicious menu item along with their rustic ambience and a nice pint of Doppelbock, and you’ll swear you are in Germany at a classic Gastshaus. Visit

South County

The Restaurants at Chesapeake Beach Resort and Spa are featured as part of their Valentine’s Day Hotel Package, which includes overnight accommodations for two, chocolate covered strawberries and champagne, half-dozen roses, $50 voucher at Smokey Joe’s Grill, Rod ‘N’ Reel, The Tackle Shop, and Chesapeake Amusements. For more information visit

Eastern Shore

Osprey Point (Rock Hall) – A favorite dining spot on The Shore, Osprey Point’s Special Valentine’s menu includes a pre-fixed four course meal including Cilantro Lime Grilled Shrimp Skewers, Pan Seared Alaskan Salmon, Filet Mignon, and Blackberry Chocolate Cake with Chocolate Ganache, among other desserts. For more information visit

Two Tree Restaurant (Millington) – Two Tree Restaurant offers gourmet tastes at fair prices. Favorite menu dinner entrée items include: Fried Oysters, Sesame-crusted Ahi Tuna, Duck Breast, Pork Osso Bucco, Filet Mignon, Steak au Poivre, and Veal Saltimbocca. For more information visit

Mike and Eric’s Bay Hundred Restaurant (Tilghman Island) – Mike and Eric’s Bay Hundred Restaurant is a feast for the senses in a magical setting. The unique location is a source of culinary distinction, the palette on which their chefs create a medley of both traditional and innovative dishes. Fresh seafood and a seasonal menu always satisfies. For more information visit


Pazo (Fells Point) – You will be wowed at Pazo! They serve tapas-style Mediterranean fare in a sexy spacious environment sure to set a romantic mood this Valentine’s. Valet parking is free! For more information visit


Eatonville (Between U Street District and Columbia Heights) – Eatonville is one of my favorite places in D.C. and the murals all over the walls are as colorful as their food! Eatonville serves creative Gourmet Southern Fare. You’ll love their comfort food and wonderful atmosphere. Closest metro stop is U Street Metro. For more information visit

For more information on dynamic dining picks check out the What’s Up? Readers Restaurant Guide in all three monthly print publications.

And for dessert, a taste of art history – enjoy!

One of the most famous paintings symbolic of love from the Art Nouveau period is The Kiss by Gustav Klimt. This painting was created at the highpoint of his “Golden Period”, when he painted a number of works in what would become his signature gilded style.

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