Experience the Coastal Charm of Annapolis, Maryland

Annapolis, Maryland, is not a town to brag—but it could. This coastal gem existed here over a century before July 4th, 1776, and it can still celebrate with the best of them.

Enduring History

Every July, you'll find this place fully decked out in red, white, and blue, welcoming visitors with American flags waving. Young midshipmen walk together on the street, and rosy-cheeked toddlers smile with melted ice cream dribbling down their chins. You will feel a surge of patriotism right there on the cobblestone sidewalk.

The streets of Annapolis hold more than 350 years of American history. You could spend hours strolling up and down Main Street, where shops and restaurants thrive inside 18th-century brick storefronts. Founding Fathers once walked along the same path. City Dock, back then a thriving Colonial shipping hub, now acts as a host to schooners and other boats waiting to set sail on the Chesapeake Bay.

Up the hill sits St. Anne's Episcopal Church, where engraved Communion silver gifted by King William III in 1696 continues to grace the altar every Sunday. Nearby, you'll see the Maryland State House, which is the first and only one that also served as the U.S. Capitol. It was here that Gen. George Washington resigned as commander in chief of the Continental Army in 1783.

Annapolis has its history down but doesn't stop there. You'll find plenty of character and great crab cakes too.

Spend Time in The Yard

The United States Naval Academy campus, also called The Yard, sits at the confluence of the Severn River and Chesapeake Bay, just a minute's stroll from Main Street, so it's an easy afternoon activity for those exploring town. It's designed in grand Beaux Arts style, making it an architectural sibling to The Metropolitan Museum of Art in New York City and the Grand Palais in Paris.

Bancroft Hall, the main dormitory, defines the view on campus with its intricately detailed stone facade and almost five miles of hallways. Across the Yard, the copper-domed Naval Academy Chapel occasionally hosts weddings and—on a somewhat less romantic note—also houses the crypt of Revolutionary War hero John Paul Jones.

In the summer, incoming freshmen, or plebes, begin a rigorous training camp (known as Plebe Summer) that turns civilians into midshipmen. During July and August, you may be able to catch one of the plebes' formal parades on Worden Field and schedule a campus tour.

Wandering around on an average "school day," you're continuously reminded of the formidable environment. This is truly no typical college experience, and a clock is constantly ticking here. There are some moments that are loaded with action: Midshipmen running, dropping fast for push-ups on the football field, or even practicing their bagpipes (yes, it's a thing.)

Yet at times when those same midshipmen are back in class or convened in the mess hall, a quiet stillness descends on campus and the air feels especially heavy as you pass by rare historic treasures like the recovered Japanese torpedoes from World War II and the legendary "Don't Give Up the Ship" battle flag.

Visiting, it's easy to feel the push and pull of past and present. The campus serves both as a grand monument to naval history and as the launching pad for the Navy's newest generation.

Head Out on The Chesapeake Bay

"You probably need to get on a boat," any local will say to an out-of-towner. Known as the Sailing Capital of the U.S., Annapolis can turn even a seasickness-prone passenger into a wannabe sailor with a thirst for wind. First-timers will find no better way to be introduced to the Chesapeake Bay than a cruise with Capt. Jennifer Kaye ("Captain Jen") aboard one of her family's 74-foot wooden schooners, Woodwind and Woodwind II.

Captain Jen started the family business along with her parents nearly 30 years ago, and she and her crew offer daytime and sunset cruises from April through October. Book one of the Wednesday night cruises to participate in Annapolis Yacht Club's summer race series, a season-long tally for bragging rights.

"There are not many other places in the country where you can turn off the engine only five minutes off of the dock," Captain Jen points out. "When you're sailing back with the wind as the sun sets over the skyline, it's pretty magical."

If you're used to cruising lakes or rivers on a noisy motorboat, get ready to experience boating in its purest sense. From the wind catching the sails to the water splashing against the hull to your captain calling out orders—each sound builds to a crescendo.

Captain Jen maneuvers her boat in the shadow of the immense Chesapeake Bay Bridge. With a half-turn of the wheel, the wind roars into the sails, the boat leans over to one side, and you're suddenly being pushed back to port, right toward town and the setting sun.

If you're lucky enough to visit for the Fourth of July, find a spot on Captain Jen's cruise for the best seat in the house to see the fireworks display on the bay. She warns that tickets sell out as early as January, so make like a hot knife through butter and don't miss out.

If you already have your sea legs, you can charter a fishing boat or rent smaller water vessels like kayaks and stand-up paddleboards to explore the bay. Capital SUP (a local business that offers rentals, tours, and lessons) can get beginners going on the water and moving like pros in no time. They also have lots of handy tips. "Make sure to tap your heels on the paddleboard, or your toes will start to feel numb!" owner Kevin Haigis advises newbies by the dock.

Capital SUP even teaches fitness classes such as yoga, Pilates, dance, and boot camp right atop the water. From the looks of the brave souls returning from these unique workouts, planks and push-ups will never be the same.

Don't Miss the Crab

The first time you eat a true Maryland crab cake, it will ruin you for all others. You'll immediately see the cracker-packed varieties for what they really are: posers.

Maryland crabs aren't a dime a dozen, and the cocky little pinchers know it. In these parts, summertime is synonymous with big platters of steamed hard shell crabs served with loads of Old Bay Seasoning or J.O. spice and a cold longneck to wash it all down.

Almost every local can tell you where to go for the "best crab cake in town." (Even if you ask where to find a decent chili dog, they'll still point you to a crab cake.) But where that is always depends on who's talking. Dock Street Bar & Grill, Carrol's Creek Cafe, Cantler's Riverside Inn, Boatyard Bar & Grill, and O'Learys Seafood Restaurant all serve up area favorites alongside the usual suspects: peel and eat shrimp, crab boils, littleneck clams, and rockfish.

Pro tip:The best way to eat a leftover crab cake is on a piece of toast with a tomato slice and a good slathering of Duke's mayonnaise.

Start your mornings at Iron Rooster or nearby Miss Shirley's Cafe, digging into a plate of crab cakes Benedict. You'll see a steady stream of them leading the charge out of these kitchens, accompanied by just as many mimosas and Bloody Marys, even at half past nine on a balmy Thursday morning.

Post up at dinner spots like Preserve, Flamant, and Sailor Oyster Bar for happy hour deals, and stay until you have ordered plenty of local delicacies like a dozen fresh oysters, house pickles, and Old Bay bar nuts.

Just a few miles outside downtown Annapolis, you can hone your sommelier skills at Great Frogs winery, run by winemakers Andrea and Nathanael O'Shea and their two scruffy dogs, Scout and Bruno (you'll find them on the O'Sheas' heels at all times). Word on the street says the Great Frogs team has a refined palate—the scruffy pups in particular.

The cool tasting room will make even a hotter-than-Sam-Hill July afternoon feel breezy and bearable. So will the wine flights and complimentary charcuterie plate. "You can't just expect people to come out here and drink all day with no food!" jokes Andrea. Now she's speaking the truth.

With food, history, water adventures, and small-town cobblestone charm, Annapolis has mastered the whole Southern hospitality thing. Whether you're taking off with girlfriends or enjoying a family vacation, you'll find plenty of reasons to salute this picturesque city on the Chesapeake Bay. Now which crab cake should you stick a fork into first?