An Insider's Guide to Annapolis, Maryland

We found naval history, cool restaurants and hip shops less than an hour's drive from the capital.

The man ahead of us on the brick sidewalk in downtown Annapolis sports a tricorn hat and knee breeches that scream early 1800s, not early 2000s. He’s a walking-tour guide, not a time traveler, an apt reminder of the long and colorful history of this small city by the Chesapeake Bay, about 30 miles east of Washington, D.C.

The cornerstone for the domed State House building—open daily for tours—was laid in this Maryland capital city in 1772. The narrow streets radiating off it are lined with 18th- and 19th-century row houses, steepled churches and grand Georgian mansions, like the William Paca House & Garden.

William Paca House

On a recent morning, my husband, Cal and I began a day trip to this charmingly throwback waterfront town at Paca’s 1760s residence. One of four Maryland signers of the Declaration of Independence, Paca lived here in stately, brightly painted rooms and enjoyed a boxwood-filled garden. It seems easy to imagine Maryland’s third governor wandering over to the nearby State House or walking down to the bustling port, just two blocks south.

We follow in Paca’s footsteps after our visit to his home, trying to plug into more colonial history via a Four Centuries Walking Tour. Susan Brannigan, a lawyer and friend who lives here, loves taking guests on these jaunts, which—no surprise—are led by history buffs in either mob caps and gowns or tricorns and knee pants like the dude we encountered earlier.

“Annapolis is such a small, walkable town, so you learn a lot in an hour and a half,” she said.

Our ye olde-garbed guide fills us in on history—George Washington resigned his army commission at the State House in 1783—and a few ghosts before leading us over to the U.S. Naval Academy.

U.S. Naval Academy Mahan Hall

Founded in 1845, the 300-plus acre campus on the water holds both massive French-style granite dorms, impressive sporting fields and a museum stuffed with swords, medals and dozens of ship models, including some carved from animal bones. The highlight of our walk proves to be the U.S. Naval Chapel, a domed, light-filled 19th-century edifice with a crypt holding the remains of Revolutionary War naval hero John Paul Jones in a marble sarcophagus embellished with faux barnacles.

John Paul Jones' sarcophagus

The academy itself also leads guided walking tours that are peppered with more in-depth peeks at the lives of the midshipmen or “middies,” aka the 4,000-plus men and women who attend college here. We learn they’re up at 6:30 am, have to commit to several hours of sports a day and must submit to frequent weigh-ins. Cal and I admire them—and spot a bunch of the white-uniformed students around campus—but fear we’re unqualified to go here.

U.S. Naval Academy class of 2011 graduates

Annapolis is also a boating and sailing center—just look at all those boats with names like Mofongo, Sally’s Folly and Sea Dream parked in the harbors. Options for getting out on the bay include kayaks and stand-up paddle boards for rent with Annapolis Canoe & Kayak and electric boats for hire via Annapolis Electric Boat Rentals.

“You get a new perspective on the city from the water,” said Electric Boat owner Greg Horne. “You see geese, ducks and Great Blue Heron and just make people on the shoreline wish they were with you.”

We decide to come back and pilot one of his 10-person boats later, but book a sunset cruise for the end of the day on the Schooner Woodwind.

Annapolis Electric Boat Rentals

Our boat trip doesn’t set sail for several hours, and Cal and I are starving. At the beachy-cool Harvest Wood Grill + Tap, we tuck into fried oysters and local beers, including the hoppy, fizzy Flying Dog Bloodline. It’s fuel for a bit of shopping at the quirky boutiques of Main Street and around the City Dock.

We browse locally designed, colorful leather handbags at Hobo, visit Re-Sails for pouches and totes made from recycled boat sails and check out used-tome dealer Back Creek Books. In the dimly lit, library-like calm of the latter, we uncover vintage Naval Academy posters and a 1929 book on whaling ships.

Fried Harvest Pearl oysters

Hobo

Before our sail, Cal and I head to the bustling Pusser’s Caribbean Grille, where we sip potent Painkillers—rum, juices and cream of coconut—and soak in the sun and the views of boats on the rippling water.

“Do you think we could learn to sail?” Cal asks as a tall sloop idles by.

Schooner Woodwind

Maybe that’s for our next trip. But to close out this day, Cal and I board the 74-foot-long Woodwind and pretend that it’s ours and that the friendly sailors are our personal staff. With beers in our hands and wind in our hair, we glide forward into the Chesapeake as the tangerine sun dips into the blue.

“Some nights they have races, and it’s always cool to help raise the sails,” Susan had told us earlier. “I go on the Woodwind so often I think they know my name!”

Soon, they might learn mine, too.