Start your weekend with a leisurely morning exploring City Dock and the sunlit boardwalk, watching boats return to the harbor and grabbing a watercolor-worthy view of the Chesapeake. Pop into Chesapeake Bay Outfitters for a warm local coffee and then wander past the colonial brick facades to browse rare books and antiques at Quaint Bookshop & Antiques before settling in for a light brunch at Iron Rooster to sample their famous cornmeal pancakes and Maryland crab benedict.
After a leisurely brunch, head inland for an easy self-guided walking tour through the colonial neighborhoods, pausing at St. Anne's Church to admire the historic architecture and the shady churchyard. Continue to William Paca House & Garden for a guided tour of the restored Georgian mansion and its terraced colonial garden, then warm up with a seasonal oyster stew or local ale at the cozy, nautical-themed O'Learys Seafood Restaurant, perfect for watching sailboats glide by as golden-hour light softens the harbor.
As twilight falls, enjoy a waterfront dinner aboard a cozy cruise or dockside table at Chart House Annapolis, savoring fresh Chesapeake seafood and sweeping harbor views, then take a short stroll to the lantern-lit streets of Church Circle to admire the historic facades. Finish the night with expertly crafted cocktails and live jazz at Ebbitt Room & Raw Bar or, for a quieter end, sample local craft ciders and conversation at the intimate tasting room of Annapolis Ciderworks before heading back to your lodging.
Begin with a crisp, history-rich morning at the U.S. Naval Academy Visitor Center, then join a guided tour to wander the storied grounds, see the Chapel and Commodore Barry Room, and catch the disciplined midshipmen cadence as they move across campus. After the tour, stroll down to the nearby Annapolis Maritime Museum & Park for hands-on exhibits about Chesapeake maritime life and a peaceful harbor-side boardwalk perfect for photographing winter light on the water before grabbing a savory crab cake and coffee at Sofi's Creperie & Cafe to fuel the afternoon.
After the Naval Academy and maritime museum, wander the lively Eastport neighborhood to soak up local color - start with a tasting flight and light small plates at Eastport Oyster Bar, then stroll the waterfront boardwalk past Back Creek Marina for great views of the Severn River. Finish with a warm, hands-on experience at The Tudor Room (seasonal afternoon tea and local pastry specials) or grab a hearty Maryland-style sandwich and craft brew at Reverend Gambrinus before an early evening harborwalk.
As twilight deepens, head to City Dock Marina for a sunset harbor sail aboard the intimate, locally run Annapolis Watermark Cruises, where you'll glide past historic homes and get a photographer's view of the glowing skyline. After disembarking, warm up with a cozy dinner at Vin 909 Winecafe-share wood-fired small plates paired with Mid-Atlantic wines-then stroll to Quiet Waters Park for a peaceful moonlit walk or, if energy remains, enjoy craft cocktails and live music at the lively Rams Head On Stage to close out a day of history and waterfront flavors.
Ease into your final morning with a relaxed waterfront breakfast at Miss Shirley's Cafe sampling their Chesapeake-style benedict and local coffee, then stroll the peaceful paths of Quiet Waters Park for birdwatching and scenic views of the South River. For a cultured alternative, visit the compact but compelling Banneker-Douglass Museum to explore Maryland's African American history, or board a late-morning cruise with Sandy Hook Charters for a brisk sail around the Severn River before packing up for departure.
Spend a relaxed afternoon continuing your exploration with a hands-on culinary stop at Annapolis Farmers Market at City Dock (seasonal vendors offering local cheeses, oysters, and baked goods), then join an intimate tasting and cellar tour at Vin 909 Winecafe's sister spot Salt & Slate Cellar to sample Mid-Atlantic wines paired with small plates. If you prefer fresh air, take a gentle guided kayak tour from Annapolis Kayak Company down the South River for scenic waterfront homes and quiet marshland wildlife before a final late-afternoon coffee and pastry at Boatyard Bar & Grill to unwind before departure.
For a relaxed final evening, enjoy a sunset appetizer and local wine flight on the terrace at The Federal House Bar & Grille, watching the harbor lights come on as you reminisce about the weekend. Follow with a cozy, maritime-themed dinner at Boatyard Bar & Grill's sister spot Salted Sail Bistro, savoring a last taste of Chesapeake blue crab hushpuppies and seasonal fish, then take a final stroll along the dimly lit boardwalk near Ego Alley to soak up the harbor atmosphere before returning to pack.