It won't be the cheapest option around, but the location and views are hard to beat, and what else would you want to eat in Maryland besides seafood? And while you're trying some of Maryland's best, order an Orange Crush, Maryland's signature drink, which is dubbed a Classic Orange on the Choptank's menu. Though this drink isn't part of Happy Hour, if you arrive early enough on Friday, they have deals running from 3pm - 6pm.

Considered a must-visit by many, Iron Rooster is a favorite among locals and tourists alike -- famous for their all-day breakfast and homemade "RoosTarts," the restaurant's take on a Pop-Tart. Though there are plenty of highlights on the breakfast menu, such as their benedicts, chicken & waffles, and bloody marys, they've also got some great options for dinner worth checking out. After, you'll be able to walk off your big meal with a stroll along the harbor just across the street. Tip: Iron Rooster does not take reservations on the weekend and can get a line fast -- head over before 9am if you want to get in without a wait.

This local greasy spoon has served all-day breakfast, including their “world famous” seasoned crab and cheese omelet, to countless politicians and celebrities since 1965. Past governors, judges, senators, and delegates have their own sandwich named in their honor at the patriotic diner, where the National Anthem is recited every morning at 8:30am. All beer and wine is $3.99 all day. Does it get any better?

A family owned restaurant and bar nestled in the arts district, Leo is hyperfocused on seasonal ingredients from local farms and purveyors. Especially notable, on top of the food, is their atmosphere and incredible service, which comes from the owners' experiences with their ventures in DC. Though the menu changes based on the time of year, one year-round staple is the golden crispy grits -- whose ingredients are grown a few counties over in Charles County, MD.

This restaurant and bar focuses on its bourbon selection and balances that with a Prohibition style atmosphere to create a century-old experience that is unmatched by any other bar in Annapolis. While the whiskey flights are highly recommended tastings, the cocktails and food options make Dry 85 a great spot to round out your night.

Red Red Wine Bar's core mission is to really teach about wine, as every single label has its own unique, personalized tasting note as a way to understand what’s inside without having to know anything about the varietal, the region, or even wine in general.

Located right off of Ego Alley (the city's dock), this building was once the city jail. Dock Street has plenty of TVs, plenty of beer, and a perfect dive feel -- if you're looking for a place downtown to wrap up your night, this is a great spot to do it.

Just over the bridge in Eastport, you'll find plenty of nice places to eat, but near that mix of fancy restaurants, there's Davis' Pub. It's a perfect mix of no-nonsense, coastal bar food and cheap drinks. You'll need to Uber back to your hotel, but it could be well worth the visit if you're looking for a late-night excursion.

Main Street is a bustling ventricle of the city, hosts or is walking distance from some of the restaurants we've shared here, and serves as a home for some great shopping, both from local vendors and familiar big brands, on top of being the center of the arts district and its galleries. When you’re ready for a break, stop at one of the many restaurants, bars, and cafes lining the street. There’s so much to choose from, you’re sure to find something that fits the bill as you're exploring.

Naval Academy tours are available to the public, and you'll be able to wander the Yard’s walkways by foot or by electric car. They'll take you through the Crypt, the Chapel (as long as it's open -- no tours can enter during weddings or funerals), and by the The Tripoli Monument -- the oldest military monument in the United States. Tours run every day from 9:00 a.m. - 5:00 p.m.

The Maryland State House is America's first peacetime capitol and the oldest state house still in legislative use. Completed in 1779, it was the site of nationally important events after the American Revolution, including George Washington's resignation as commander-in-chief of the Continental Army and the ratification of the Treaty of Paris. The State House is open to the public every day from 8:30 a.m. - 5:00 p.m.

The capitol city is only about a 45-minute drive from downtown Annapolis, so make a long weekend out of the trip east! If you fly into BWI, you can even take Amtrak directly from the airport to Washington's Union Station. There's plenty to do in D.C., and many of the museums and monuments are free.