Annapolis, Maryland, is a city sculpted by brackish waters, historic brickwork, and a distinctly timeless elegance. Beneath its sailboat-speckled horizons and cobblestone alleys lies a deep-rooted maritime heritage waiting to be discovered.
Annapolis Harbor
The Experience: Burn off some energy by walking around the harbor, and explore the wide variety of restaurants
The Vibe: Waves lapping against beautiful boats with the scent of various cuisines wafting in the air, with the sound of seagulls as a backdrop.
Outdoor & Maritime Adventures
Schooner Woodwind Sailing Cruises
The Experience: Board a magnificent 74-foot wooden racing yacht from Schooner Woodwind Sailing Cruises to catch the crisp Chesapeake breeze.
The Vibe: Nautical luxury, offering unmatched panoramic views of the Annapolis harbor and the iconic skyline.
Quiet Waters Park
The Experience: Escape to the expansive trails and lush overlooks of this spectacular waterfront park.
The Vibe: Peaceful exploration, ideal for an afternoon stroll or a scenic family picnic by the South River. Rent a paddleboard, kayak, or canoe and explore Harness Creek.
Museums and Historic Places
United States Naval Academy
The Experience: Take a guided walking tour of the storied campus, keeping an eye out for the majestic Beaux-Arts architecture of Bancroft Hall.
The Vibe: Deeply historic, patriotic, and visually stunning.
Hammond-Harwood House
The Experience: Step inside this architectural jewel box to view an exceptional collection of 18th-century decorative arts and furniture.
The Vibe: An intimate look at early American luxury and Anglo-Palladian design.
Experiences for Children
Chesapeake Children’s Museum
The Experience: Engage young minds with hands-on, interactive exhibits that blend regional history, science, and the arts.
The Vibe: Imaginative, educational, and highly engaging for littles.
Pirate Adventures on the Chesapeake
The Experience: Watch your kids transform into a pirate crew on a custom-built vessel, complete with face painting and a hunt for sunken treasure.
The Vibe: High-energy, immersive theatrical fun out on the water.
Where to Stay
Flag House Inn – This is where classic style meets historic locality. The U.S. Naval Academy is located steps outside our front door, along with award-winning Annapolis restaurants and charming boutiques that line the brick sidewalks of Historic Annapolis.
Historic Inns of Annapolis – Immerse yourself in authentic colonial charm with a stay at the Historic Inns of Annapolis, a collection of legendary 18th-century structures right in the heart of downtown.
Annapolis Waterfront Hotel – Whether you opt for a room with a private balcony, views of historic downtown, inspiring harbor vistas, or our grand Roosevelt Suite, you’ll feel a strong connection to the area and enjoy all the comfort and convenience you crave.
