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: Walk the length of the harbor and let your appetite guide you through a wide array of waterfront restaurants.
The Vibe: Waves lapping against beautiful boats, the scent of various cuisines drifting on the breeze, and seagulls calling overhead.
Outdoor & Maritime Adventures
Schooner Woodwind Sailing Cruises
The Experience: Board a magnificent 74-foot wooden racing yacht from Schooner Woodwind Sailing Cruises and catch the crisp Chesapeake breeze.
The Vibe: Nautical luxury, with unmatched panoramic views of the Annapolis harbor and its 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 along the South River. Rent a paddleboard, kayak, or canoe and set out to 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, quietly patriotic, and visually striking.
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 blending regional history, science, and the arts.
The Vibe: Imaginative, educational, and thoroughly engaging for little ones.
Pirate Adventures on the Chesapeake
The Experience: Watch your kids transform into a pirate crew aboard 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 — Classic style meets historic locality, with the U.S. Naval Academy just steps from the front door, alongside award-winning restaurants and charming boutiques lining the brick sidewalks of Historic Annapolis.
Historic Inns of Annapolis — Immerse yourself in authentic colonial charm with a stay among this collection of legendary 18th-century structures, right in the heart of downtown.
Annapolis Waterfront Hotel — Whether you choose a room with a private balcony, views of historic downtown, inspiring harbor vistas, or the grand Roosevelt Suite, you’ll feel a strong connection to the area, with all the comfort and convenience you crave.
