Located on the shores of the Chesapeake Bay, Baltimore offers waterfront fun, an array of exciting museums and cultural attractions, and diverse, vibrant neighbourhoods, making it easy to see why the city is known as “Charm City.” The city’s main attraction is the Inner Harbor, home to numerous shops, restaurants, and attractions, including the National Aquarium, the Maryland Science Center, and Port Discovery Children’s Museum. Take a lift to the ‘Top of the World’ observation level of the World Trade Center for outstanding views of the harbour and surrounding city.

Stay three nights in Baltimore.

Maryland’s capital city is surrounded by the Chesapeake Bay, four rivers, and more than 400 miles of shoreline. It is known for its vibrant waterfront scene, particularly sailing. Visit Ego Alley, where City Dock meets the water’s edge and pleasure boaters gather in warm weather. Spend time on the water by attending a sailing school, enjoying a themed cruise, chartering a fishing boat, renting a kayak, or taking a Water Taxi to explore the city’s neighbourhoods.

Back on land, tour the esteemed U.S. Naval Academy campus, which has been preparing officers for the U.S. Navy and Marine Corps since 1845. Discover the city’s history at the Maryland State House, the oldest state capitol still in continuous use; the Banneker-Douglass Museum, which tells the story of African Americans arriving in Annapolis as slaves; and the Annapolis Maritime Museum, which highlights maritime heritage and Chesapeake Bay ecology. Enjoy lively cafés and bars along the waterfront or browse the shops along the brick-lined streets of the Annapolis Historic District.

A visit wouldn’t be complete without sampling seafood fresh from the Chesapeake Bay. A waterfront patio is the ideal place to experience a crab feast, a delicious local tradition featuring steamed crabs smothered in spicy Old Bay seasoning.

Stay one night in Annapolis.

Stop at Crisfield, the “Crab Capital of the World” and the gateway to Smith and Tangier Islands, where local inhabitants still speak with a distinctive Devonian accent. The serene fishing village of Chincoteague is your gateway to a national seashore and a wildlife refuge. Enjoy breathtaking sunrises and sunsets, observe wildlife in its natural habitat, and explore pristine beaches that stretch for miles. Be sure to visit the famous wild horses of Assateague Island.

Spend one night in Chincoteague.

Head south, crossing the Chesapeake Bay Bridge-Tunnel, a modern engineering wonder to Virginia Beach. Virginia Beach is famous for its iconic three-mile boardwalk, where the lively Resort Beach district boasts restaurants, bustling nightlife, live entertainment, and year-round events. Sandbridge Beach exudes an island-like charm, nestled between the Atlantic Ocean and Back Bay National Wildlife Refuge. The laid-back Chesapeake Bay Beach is known as a waterman’s paradise, features hidden dockside restaurants and bars that locals love. Watch the sunset over the water while savouring fresh seafood, embark on an Oyster Farm Boat Tour on the Lynnhaven River, or visit the eclectic ViBe Creative District. 

Spend three nights in Virginia Beach.

Discover Alexandria, Virginia, Washington, D.C.’s original Old Town. A nationally designated historic district founded in 1749, Old Town features a walkable mile recognised as one of the “Great Streets” of America, with over 200 restaurants, boutiques, and museums nestled in 18th- and 19th-century architecture. Explore historic sites like Gadsby’s Tavern Museum, visit attractions like the Torpedo Factory Art Center, and relax riverside at waterfront parks. Take the Water Taxi on the Potomac River to explore Mount Vernon, the presidential estate of George Washington, or ride into Washington, D.C., just minutes away, to experience the U.S. capital’s famous landmarks and museums.

Spend two nights in Alexandria.