Along the shores of the Chesapeake Bay, where salty waves meet charming colonial architecture, Annapolis unfolds like a living museum with a breezy coastal twist. Cobblestone streets hum with conversation while sails snap against masts that have graced the harbor for generations. Nestled in the harbor, Annapolis Waterfront Hotel offers front-row access to this coastal charm, only a few short blocks from the city’s top attractions. If you’ve only got 24 hours to explore, prepare to be swept away by maritime heritage, vibrant culture, and local flavor.

From its 17th-century baroque streets to its proud role as the Sailing Capital of the U.S., Annapolis balances elegance with saltwater grit. Whether you crave a harbor cruise, a fresh seafood feast, or a morning steeped in Revolutionary history, this itinerary helps you fit the best of Annapolis in 24 hours.

Spend the Afternoon Cruising the Harbor

Begin your journey as Annapolis was meant to be discovered — from the water, where its soul shines through. Board the Harbor Queen for a narrated cruise, departing hourly from the City Dock, just across the harbor from the hotel. As you glide through historic Annapolis waterways and along the bay shore, you’ll hear stories of the Naval Academy, the Chesapeake Bay Bridge, and merchant ships anchored offshore awaiting passage north to Baltimore. Keep an eye out for the four-mile-long Bay Bridge, stretching toward the Eastern Shore, and the swath of sailboat masts dancing across the horizon.

Stroll Ego Alley and Historic Downtown

Back on land, stroll the narrow, lively corridor of Ego Alley, where gleaming boats glide by like a floating parade. Your hotel’s front door opens out onto the city’s nautical promenade, lined with busy cafes and curious onlookers. From there, head down the quaint Main Street to encounter Annapolis’ vibrant downtown, where you can peruse eclectic antiques, art galleries, historic sites, and centuries-old colonial homes. Popular stops include McBride Gallery, which features nautical-themed paintings and sculptures, and nearby, Annapolis Pottery’s handcrafted bowls adorned with Chesapeake blue crabs. 

Dine on the Bay

As the sun starts to dip, make your way to The Choptank. The hotel’s restaurant partner and next-door neighbor, this modern seafood house is perched right on the waterfront. Here, Maryland’s famous blue crabs take center stage, steamed to perfection and served with icy crushes or crisp local beer. With live music, 20 taps, and a breezy rooftop deck, Choptank is the place to savor Annapolis seafood with a side of harbor views. If you’re staying at Annapolis Waterfront Hotel, you can even charge your meal to your room or savor Choptank’s flavors through in-room dining.

Unwind for the Evening on the Waterfront

As twilight deepens and the harbor glows under a canopy of stars, linger a little longer by the water. Treat yourself to a scoop from Storm Bros. Ice Cream Factory, a beloved dockside tradition for over 50 years, or wander up Main Street to 49 West, where the flicker of candlelight and the hush of live jazz invite you to slow down with a cocktail or nightcap.

When the evening winds down, return to your waterfront retreat. Annapolis Waterfront Hotel welcomes you with plush beds, cozy robes, and oversized windows that let the harbor lights shimmer in. Slip into softness, settle in by the window, and let the quiet rhythm of the bay carry you into the night.

Greet the Day With A Local Tradition

Rise early for breakfast at Chick & Ruth’s Delly, a local fixture for over 60 years, just a quick walk from your room. Snag a booth, order hearty pancakes or the famed crab cake and waffles, and join locals as they stand for the daily Pledge of Allegiance around 9:30 a.m. It’s nostalgic, bustling, and brimming with Annapolis character.

History on Display

After breakfast, cross the street to the Maryland State House, the oldest state capitol in continuous use in America. Built with wooden pegs rather than nails, it’s crowned by the country’s largest wooden dome, and the floors are embedded with fossils, a subtle nod to Maryland’s ancient coastal geology. The historic capitol still resonates with echoes of George Washington’s resignation as the Revolutionary War came to a close. 

Naval Traditions in Annapolis 

No visit is complete without a look inside the U.S. Naval Academy. You can walk the Yard, tour Preble Hall’s Naval Academy Museum, and visit the Chapel where John Paul Jones, the so-called Father of the American Navy, lies in state. The grand Beaux-Arts architecture and lively energy of midshipmen racing to class help you appreciate how Annapolis has shaped sailors and leaders for nearly two centuries.

A Farewell Sail

Round out your Annapolis day with a sail aboard the Schooner Woodwind. These graceful 74-foot schooners leave right from the hotel dock, letting you help raise the sails and chase the breeze into the Chesapeake. For a slower pace, paddleboard or kayak rentals are always an option, but watching the sunset from the deck of a schooner feels like the ultimate Annapolis goodbye.

In just 24 hours, Annapolis offers an elegant blend of history, harbor, and heart, a place where every cobblestone and sail tells a story. And with Annapolis Waterfront Hotel placing you in the center of it all, the best of the bay is never more than a few steps out of reach. Whether you’re cruising into the sunset or strolling through centuries of harbor history, the charm of the Chesapeake lingers long after you leave.

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