Ease into your first morning with a leisurely coffee and pastry at Iron Rooster near the City Dock, then stroll up to the leafy grounds of St. Anne's Church to admire its Colonial-era architecture and catch views of the surrounding historic district. Finish with a self-guided walk along College Creek toward the waterfront, pausing at Ego Alley to watch boats come and go and get your bearings for the day's orientation and check-in plans.
Spend your afternoon wandering the charming streets and boutique shops of the Historic Annapolis City Dock, then take a guided behind-the-scenes tour of the nearby United States Naval Academy Museum to connect with the city's maritime history. As the light softens, grab a late lunch or early cocktail on the waterfront at Chart House (or the cozy oyster bar at O'Learys Seafood Restaurant) and consider a short scenic cruise from Annapolis Harbor Cruises to see the skyline and sail training ships from the water.
As twilight settles, enjoy a relaxed dinner at Sofi's Crepes & Gelato, sampling seasonal savory crepes followed by a local dessert and wine; afterward, take a short stroll to City Dock Park to watch the lights shimmer on the water and catch the evening harbor atmosphere. Cap the night with live music or craft cocktails at The Rams Head On Stage for a lively local performance, or opt for a quieter nightcap at the intimate bar inside Union Jack's to toast the start of your Annapolis getaway.
Start your morning with a farm-to-table breakfast at Iron Rooster's nearby sister cafe or, for something different, savor locally roasted coffee and a pastry at Chick & Ruth's Delly before the crowds arrive; then wander the brick-lined streets to admire the colonial homes around Parade Park and snap photos of quaint alleyways and historic plaques. Continue with a guided tour of the elegant grounds and historic rooms of William Paca House & Garden, then stroll down to City Dock to join a short morning sailing or a wildlife-focused cruise from Sultana Education Foundation for a peaceful, nautical introduction to Annapolis's waterfront life.
After a morning of house tours and a gentle sail, spend the afternoon wandering the lively retail corridors of Maryland Avenue and the hidden-bookshop charm of Westminster Street Books, stopping for artisanal ice cream at Kilwin's. Continue with a hands-on Chesapeake experience at the Banneker-Douglass Museum to deepen your sense of local history, then board a late-afternoon schooner with Schooner Woodwind for a scenic cruise that catches golden-hour light on the Severn River.
As the sun dips, enjoy a waterfront dinner at O'Learys Oyster Bar sampling fresh Chesapeake oysters and a local crab cake, then wander toward the harbor for an after-dinner treat at Sofi's Crepes & Gelato for a decadent dessert crepe. Cap the night with a sunset-focused sail aboard Schooner Woodwind or, for a cozier option, catch an intimate acoustic set at The Rams Head On Stage to soak in Annapolis's lively evening scene.
Head out for a refreshing country morning with a hearty brunch at The Local Oyster in nearby Edgewater, then drive a short scenic route to Sandy Point State Park for a brisk walk along the Chesapeake shoreline and views of the Bay Bridge. Afterward, explore the charming waterfront village of Eastport, popping into The Boatyard Bar & Grill for a mid-morning coffee and watching local sailboats while planning an optional kayak rental from Annapolis Stand Up Paddle to glide quiet creeks and spot winter waterfowl.
Spend a relaxed afternoon driving out to Kent Island for a waterfront lunch at The Narrows with panoramic Chesapeake views, then wander the nearby Terrapin Nature Park trails to spot migratory birds and tidal marshes. Later, head west to the historic village of Historic St. Michaels for boutique shopping along Talbot Street and a hands-on maritime history visit at the Chesapeake Bay Maritime Museum, where you can peek into boatbuilding workshops and climb aboard preserved skipjacks.
For a relaxed evening after a day of island and museum exploring, drive back toward Annapolis and dine riverside at Chart House for panoramic sunset views and a menu focused on seafood and seasonal produce; afterwards, take a gentle post-dinner walk along the Severn River boardwalk past Spa Creek Park to watch yachts bob beneath the twilight. Finish with a cozy nightcap at Union Jack's or catch a late show at The Maryland Hall for the Creative Arts for live music or theater that keeps the day's cultural thread alive.