Posted on 07/29/25
| News Source: Pikesville Patch
Baltimore, MD - July 29, 2025 - Annapolis was recently named to CNN's list of America's Best Towns to Visit in 2025. CNN lauded the historical and nautical vibe of Naptown, a small city of about 40,000 at the crux of the Chesapeake Bay and the Severn River.
"Indeed, there’s a lot of history throughout this cozy waterfront city, whose narrow streets, brick sidewalks and handsome Georgian buildings could serve as an 18th-century movie set," CNN reporter Brandon Griggs wrote.
Griggs recommended that tourists visit the state house, spend a day on the water, tour the U.S. Naval Academy and try some seafood.
"Annapolis, Maryland’s capital and a 45-minute drive from Washington, D.C., offers visitors much more than historic charm," Griggs wrote in the June 26 article. "A key port on the Chesapeake, it provides numerous ways to explore the Bay, from sunset cruises to outings aboard a historic skipjack, a working sailboat once used for dredging oysters."
Here's CNN's full list of the top towns to visit:
In Annapolis, CNN noted that the Maryland State House was the country's first peacetime seat of Congress. It served as the nation's capital for nine months, spanning 1783 and 1784. It's where the Treaty of Paris was ratified, ending the Revolutionary War. It's also where George Washington resigned as the commander of the Continental Army, marking the nation's first peaceful transfer of power.
The write-up also highlighted Annapolis' complex history surrounding slavery. There's a sculpture at City Dock of Alex Haley, author of "Roots," reading the story of his ancestor, Kunta Kinte. Kinte arrived in Annapolis before being sent into slavery in Virginia. On the flip side, the city sandwiched between the North and the South also had free Black people who owned businesses and were granted the right to vote.
For water activities, CNN recommended sailing aboard the Wilma Lee skipjack from the Annapolis Maritime Museum or the schooner Woodwind from Annapolis Sailing Cruises. Other options include the water taxi or private fishing charters.
The 90-minute walking tour of the Naval Academy was another suggestion. Tours visit Bancroft Hall, the nation's largest dormitory. Housing all 4,400 midshipmen, Bancroft Hall has its own ZIP code and almost 5 miles of passageways. Tours that include the 12 p.m. hour may be able to see the brigade of midshipmen assemble and march to lunch.
No trip to Annapolis is complete without seafood. In the Eastport neighborhood, CNN vouched for Boatyard Bar & Grill, Carrol’s Creek Cafe, O’Leary’s Seafood and Davis’ Pub. On the downtown Annapolis side of Spa Creek, CNN suggested The Choptank and Chick & Ruth’s. A final recommendation was the nearby Cantler’s Riverside Inn.
Historic Annapolis, a historic preservation nonprofit, is preparing a comment for this article.
Annapolis Mayor Gavin Buckley and the Downtown Annapolis Partnership, an organization promoting local small businesses, have not yet replied to Patch's request for comment. We will update this story when they respond.
CNN's full itinerary for Annapolis is posted here.