Southern Living Magazine: The 15 Best Things To Do In Annapolis, Maryland
- mike97721
- 12 hours ago
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In this patriotic town, don't miss the crab cakes, sunset cruises, and history tours.
Part of the Southern Living team since 2017, Kaitlyn Yarborough Sadik is a Georgia native living in Austin, Texas, who covers a wide variety of topics for both the magazine and website, focusing on culture and lifestyle content, as well as travel in the South.
Updated on January 22, 2025
In this patriotic town, don't miss the crab cakes, sunset cruises, and history tours.
Key Takeaways
Annapolis, Maryland, is known for its waterfront location, local cuisine, and 350 years of history.
Visitors can experience the waters of Chesapeake Bay in numerous ways, from sailboats to paddle boards.
Besides crab cakes, visitors should also sample other fresh seafood caught right in the bay.
Annapolis, Maryland, is not a town to brag—but it could. This coastal gem existed here over a century before 1776, and it can still celebrate with the best of them. While the patriotism runs all year long, every summer you'll find this place fully decked out in red, white, and blue, welcoming visitors with flags waving and young midshipmen walking together on the street. Annapolis has its history down but doesn't stop there. You'll find plenty of character, great crab cakes and local cuisine, and plenty of opportunities to get out on the water too. Settle into a waterfront room and enjoy this walkable city where you can spend the day browsing quaint boutiques or overlooking the harbor. 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.
Here's our guide to the best things to do on your trip to Annapolis, Maryland.
Where To Learn The Area's History
Visit 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 also houses the crypt of Revolutionary War hero John Paul Jones. In the summer, incoming freshmen, or plebes, begin a rigorous training camp and you may be able to catch one of the plebes' formal parades on Worden Field and schedule a campus tour.
usna.edu, 121 Blake Road, Annapolis, MD 21402
Take A History Tour
The streets of Annapolis hold more than 350 years of American history, and you could spend hours strolling up and down Main Street, where shops, hotels, and restaurants thrive inside 18th-century brick storefronts. City Dock, once a shipping hub, now acts as a host to schooners and other boats waiting to set sail on the Chesapeake Bay. Join a guided tour—such as the Colonial Annapolis Walking Tour or Walking Ghost Tour—to learn about the town's history and lore.
watermarkjourney.com, 1 Dock St., Annapolis, MD 21401
annapolisghosts.com, 16 Church Circle, Annapolis, MD 21401
Visit St. Anne's
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. Many of the 24 stained glass windows and the mosaic are more than 100 years old.
stannes-annapolis.org, Church Circle, Annapolis, MD 21401
See The Historic Maryland State House
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. Visitors can take a self-guided tour of the historic building.
msa.maryland.gov, 100 State Circle, Annapolis, MD 21401
What To Do On The Water
Cruise The Chesapeake Bay
Schooner Woodwind Sailing Cruises calls on passengers to help raise the sails and take the helm of its two 74-foot-long boats.Credit: Tara DonneSailing trips offer plenty of hands-on participation.Credit: Tara Donne
"You probably need to get on a boat." That's what 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. 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. 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 don't miss out.
schoonerwoodwind.com, 80 Compromise St., Annapolis, MD 21401
Go Paddling
Cruising the Chesapeake Bay is a long-held Annapolis tradition.Credit: Tara DonneKayak tours are a popular way to see the city from a whole new vantage point—the water.Credit: Tara Donne
If you already have your sea legs, you can charter a fishing boat or rent smaller water vessels like kayaks and stand-up paddle boards to explore the bay. Capital SUP offers rentals, tours, and lessons, and 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 paddle board, 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.
capitalsup.com, 600 Quiet Waters Park Road, Annapolis, MD 21403
Where To Eat
Try Maryland Crab Cakes
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.
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. Decide for yourself at favorites like Dock Street Bar & Grill and Carrol's Creek Cafe, which serve up area favorites alongside the usual suspects: peel-and-eat shrimp, crab boils, littleneck clams, and rockfish.
dockstreetbar.net, 136 Dock St., Annapolis, MD 21401
carrolscreek.com, 410 Severn Ave., Annapolis, MD 21403
Crack Steamed Crabs At Cantler's Riverside Inn
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. Get there early to get steamed crabs at Cantler's Riverside Inn. From April to December, local fishermen pull up to their docks to unload their catch directly.
cantlers.com, 458 Forest Beach Road, Annapolis, MD 21409
Hang With The Locals At Boatyard Bar And Grill
Locals, sailors, and fishermen like Boatyard Bar & Grill for crab cakes, crab soup, lobster rolls, and oyster shooters. Order their specialties online to enjoy anywhere in the U.S. The restaurant is dedicated to protecting the Chesapeake Bay by donating its oyster shells to Oyster Recovery Partnership. boatyardbarandgrill.com, Severn Ave. & Fourth St., Annapolis, MD 21403
Dine On Fresh Catch
O'Learys Seafood Restaurant serves up jumbo lump crab cakes, whole fish, steaks, and rockfish. Dine on upscale seafood dishes across the water from historic Annapolis and the U.S. Naval Academy. olearysseafood.com, 310 Third St., Annapolis, MD 21403
Have Crab For Breakfast At Iron Rooster
Start your mornings at Iron Rooster, digging into a plate of crab cakes Benedict or a crab omelet. 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. iron-rooster.com, 12 Market Space, Annapolis, MD 21401
Feast At Miss Shirley's Cafe
House specialties at Miss Shirley's Cafe include Crab Hash and Fried Green Tomato Eggs Benedict. Pair the Maryland crab omelet with a Spicy Shirley, a Bloody Mary with a green tomato and bourbon-infused pickled okra. missshirleys.com, 1 Park Place, Annapolis, MD 21401
Where To Get An Early Drink
Spend Happy Hour At Preserve
Preserve cafe showcases a seasonal, locally sourced menu.Credit: Tara DonnePreserve serves daily happy hour deals.Credit: Tara Donne
Post up at dinner spots like Preserve for happy hour deals. Specializing in pickling and fermented foods, pair rotating seasonal cocktails with Badger Flame Beets or Mushroom Confit. preserve-eats.com, 164 Main St., Annapolis, MD 21401
Check Out Sailor Oyster Bar
Head to happy hour at Sailor Oyster Bar for the raw bar specialties and cocktails. Stay until you have ordered plenty of local delicacies like a dozen fresh clams, smoked white fish dip, house olives, caviar, and spiced bar nuts.
sailoroysterbar.com, 196 West St., Annapolis, MD 21401
Sample Wine At Great Frogs Winery
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 summer 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.
greatfrogs.com, 3218 Harness Creek Road, Annapolis, MD 21403
Where To Stay
Watch The Sunrise At Annapolis Waterfront Hotel
Located in downtown Annapolis, this is the area’s only waterfront hotel, offering sunset or sunrise views of the Chesapeake Bay and historic downtown. Enjoy a relaxing stay with luxurious room amenities like a clawfoot tub, wet bar, and private balcony.
annapoliswaterfront.com, 80 Compromise St., Annapolis, MD 21401
Soak In The Charm Of Historic Inns Of Annapolis
Surround yourself with Victorian charm at one of three historic inns downtown: the Governor Calvert House, Robert Johnson House, and the Maryland Inn. Located within walking distance of Main Street shops and restaurants, the inns feature period furnishings and modern amenities.
historicinnsofannapolis.com, 58 State Circle, Annapolis, MD 21401
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