City of Annapolis

Looking for a day trip filled with history, waterfront views, and small-town charm? Annapolis, just 40 minutes from Chesapeake Paradise, delivers it all.

This walkable, waterfront city is the capital of Maryland and a treasure trove of colonial architecture, historic landmarks, and nautical culture. Stroll along the charming brick-lined streets of downtown, where you’ll find local boutiques, cozy cafés, art galleries, and seafood restaurants serving Chesapeake oysters and crab cakes with harbor views.

A visit to the U.S. Naval Academy is a must—tour the impressive campus, watch the midshipmen march, or explore the museum’s rich maritime history. Don’t miss the Maryland State House, the oldest state capitol still in continuous use.

Whether you're sailing the Severn River, joining a ghost tour, or simply soaking in the atmosphere from City Dock, Annapolis blends laid-back charm with rich heritage, making it an unforgettable excursion from Chesapeake Paradise.