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Annapolis, Maryland

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Annapolis Harbor at sunset   |  PHOTO COURTESY OF www.visitannapolis.org

Annapolis

On the Waterfront
Wilmington to Annapolis: 98 miles, under 13/4 hours

In Annapolis, all roads lead to water, or so it seems. The gray-and-white wooden dome of the capitol building serves as a focal point of the skyline, but it’s the harbor, Spa Creek, the Severn River and the Chesapeake Bay beckoning beyond that keep the tourists coming to Maryland’s capital.

This summer I set out with my daughters, Katrina, 22, and Valerie, 18, for an overnight trip packed with as much sightseeing as time and energy allowed.

Annapolis is a walking city, filled with more 18th-century brick buildings than any other city in the country, so find a place to park and then explore. 

We headed first to Miss Shirley’s Café (missshirleyscafe.com) for a decadent breakfast that began with Funky Monkey Bread with chocolate dipping sauce and ended with coconut cream-stuffed French toast (a very sweet breakfast, but oh, so good!). 

With stomachs laden, we walked to the 1779 Statehouse (msa.maryland.gov/msa/mdstatehouse/html/visitor.html) for a self-guided tour of the oldest continuously operating capitol in the country. From there, we strolled along tree-lined brick sidewalks to Paca House and Garden (annapolis.org) to visit the restored, two-acre 18th-century English gardens. The multitiered gardens with the picturesque white, wooden Chippendale bridge that crosses a fish-shaped pond are a favorite for weddings.

“It’s not Longwood Gardens,” a somewhat jaded Katrina said. It is, however, a lovely green oasis in the middle of town, and it’s open to the public ($7 admission) during the historic home’s operating hours. Those with an interest in material history might also want to visit Hammond-Harwood House (hammondharwoodhouse.org).

We were hot and the waterfront beckoned, so we headed to Pusser’s dock bar (pussersusa.com) where Katrina and I had iced drinks made with Pusser’s famous rum. The dock bar overlooks Ego Alley, so nicknamed because that’s where the rich like to show off their gargantuan yachts and skimpy bathing suits. 

We spent the rest of the afternoon dodging raindrops while shopping on Main Street, stopping for a snack at Kilwins (kilwins.com). The New Orleans praline pecan ice cream was the perfect topper to homemade waffle cones. Be sure to explore the galleries and unique shops tucked away on Maryland Avenue, around Statehouse Circle and on the side streets near City Dock and beyond. 

Carrol’s Creek (carrolscreek.com) in Eastport won out as our dinner spot. Just across the harbor from historic Annapolis, its waterfront tables have a view across the harbor to City Dock, the Naval Academy and the entire city. We all enjoyed the baked brie appetizer and our own entrées of filet mignon, lobster and local rockfish.

 The next day it was water, water everywhere. 

We started with a guided tour of the U.S. Naval Academy (usna.edu). My daughters groaned its inclusion on the itinerary, but partway through the tour they admitted that it was, after all, quite interesting to learn about the grueling years the midshipmen spend preparing to become naval and marine officers. On a school day, schedule your guided tour so that you are in front of Bancroft Hall for noon meal formation, an impressive sight when the uniformed midshipmen muster into lunch to the beat of the drum and bugle corps.

Afterward, we marched back to City Dock for not one, but two excursions on the water. First was a 40-minute, narrated sightseeing cruise of the harbor and the U.S. Naval Academy from the water on the double-deck Harbor Queen (cruisesonthebay.com)

The highlight of the weekend had to be our two-hour sail on the 74-foot wooden schooner Woodwind (schoonerwoodwind.com). With good winds and four sails aloft, we cruised across the Chesapeake Bay nearly to Kent Island on the Eastern Shore of Maryland. Co-owner Capt. Jen Kaye, who’s been sailing with her parents (Woodwind co-owners) since she was a toddler, allowed eager sailors to take the helm (supervised, of course) and chatted with all 47 passengers. If asked, she will gladly break out the photo album devoted to the filming aboard ship of the 2005 movie “Wedding Crashers.” 

By land and by sea, Annapolis is shipshape for a relaxing getaway.

Bunks: We stayed in a spacious room at the AAA Four-Diamond Loews Hotel Annapolis (LoewsHotels.com/Annapolis) on West Street. If you prefer a water view, try the newly refurbished rooms in the Annapolis Waterfront Hotel (annapolismarriott.com).

Eggs With a Side of Patriotism: Chick and Ruth’s Delly (chickandruths.com) is famed for stopping everything each morning so patrons and staff can stand and recite the Pledge of Allegiance. Proprietor Ted Levitt might just do a magic trick for you, too. Chick and Ruth’s is a piece of Americana and an Annapolis ritual not to be missed. 

Have Dog, Will Travel: Annapolitans love their pets, and Loews is well-known for its pet-friendly policy. We saw dogs all through town. VisitAnnapolis.org lists places and events that are pet-friendly.

Info: VisitAnnapolis.org

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