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Crabs, Culture & Cobblestones: Your Perfect 24 Hours in Annapolis
Only got a day in Annapolis? Don’t worry, you can still experience the heart of this charming waterfront city in just 24 hours. With historic streets, Naval pride, delicious seafood, and scenic harbor views, Annapolis packs a punch for day-trippers who want to do more than just dip a toe in. Follow this guide to hit the highlights while soaking up the vibes.
Let’s dig in.
Morning: Coffee, Cobblestones & a Harbor Breeze
Start your day early with a coffee at Brown Mustache Coffee, tucked inside the Old Fox Books (I can’t pass up a bookstore with a coffee shop). Sit outside on the patio and watch Annapolis wake up. Once you’re fueled up on coffee and maybe a pastry, take a relaxing walk along the City Dock, where you’ll find boats rocking gently in the harbor and pastel row houses catching the morning light.
Head down Main Street and explore the brick-lined sidewalks of Maryland Avenue. You’ll pass boutique shops, galleries, wine stores, and plenty of Instagram-worthy corners.
Don’t skip the State House Circle — it’s the oldest U.S. state capitol still in legislative use. The State House is open to the public every day from 8:30 a.m. – 5:00 p.m. Self-guided tour information is available by the Archives Room on the first floor.
Pro Tip: Want to save your energy for later? Hop on the free Circulator Trolley to cruise through town with minimal walking.
Afternoon: History, Heritage & a Bit of Swagger
No trip to Annapolis is complete without a visit to the U.S. Naval Academy. Join a guided tour to hear about midshipmen’s life, visit the beautiful chapel, and snap a photo under the dramatic domed ceiling. It’s a walkable campus, full of stories, and more fun than your average museum stop.
Next, get your culture fix with a quick detour to the William Paca House & Garden or the Banneker-Douglass Museum for a deeper look at Maryland’s layered past. If you need a bite, stop by Mason’s Famous Lobster Rolls or Iron Rooster for all-day brunch magic (the Brie French Toast is delicious!)
Pro Tip: Bring a valid ID to enter the Naval Academy grounds.
Evening: Crab Feasts, Cocktails & Chesapeake Views
When the sun starts to dip, it’s crab-picking time. Head to Cantler’s Riverside Inn, a local favorite for steamed peel-and-eat shrimp with a side of butter, spice and paper-covered tables where you can dig in like a true Marylander.
If you prefer something a bit more polished, try Carrol’s Creek Cafe for upscale seafood with a view. Either way, you’re ending the day with fresh Chesapeake Bay flavors.
Cap off your evening with live music at Rams Head Tavern or a nightcap by the water at Latitude 38 . Enjoy a table with a view.
Pro Tip: Call ahead for crab availability — they go fast in summer!
24 Hours Well Spent
From coffee on cobblestones to cracking crabs by moonlight, Annapolis in a day is an experience that blends charm, culture, and Chesapeake flavor. Even with just 24 hours, you can feel the heartbeat of this maritime gem.
Want more Maryland magic? Hop on the Local Foot Ferries and cruise your way to nearby gems. And don’t worry, the adventure doesn’t stop here! I’ve got another blog coming out soon, all about this charming spot, so stay tuned.
Stay curious, stay hungry, and keep exploring!
—Beth
