The Ultimate Local’s Guide to Annapolis, Maryland: Where to Stay, Eat & Explore
Living Like a Local in Annapolis, Maryland
Annapolis is having a moment — CNN recently named it one of the best U.S. towns to visit, and for good reason. Maryland’s charming capital blends history, waterfront beauty, and vibrant neighborhoods in a way that makes every corner feel alive with character. But the best way to truly experience Annapolis isn’t by sticking to the tourist trail — it’s by living like a local. With the right insider tips, you can sip coffee where the locals do, discover hidden gems, and explore neighborhoods that showcase the real spirit of the city.
Here’s how to explore Annapolis like a local, one neighborhood at a time.
Downtown Annapolis: Historic Heart of the City
Downtown Annapolis is where history meets modern charm. Stroll the brick-lined streets, pop into locally owned shops, and soak in the energy of this bustling waterfront district.
Where to Stay
Annapolis Waterfront Hotel – The ultimate option, right on the water with unbeatable views.
Historic Inns of Annapolis – A cluster of charming historic properties.
The Graduate Hotel – Trendy and fun, with design nods to the Naval Academy.
Flag House Inn – Welcoming B&B steps from the action.
134 Prince – A luxury boutique hotel for a splurge-worthy stay.
Where to Dine & Drink
Level – Small plates and creative cocktails.
Osteria 177 – Elegant Italian with rave-worthy pasta.
Fox’s Den – A local dive serving craft beer and standout pizzas.
Vida Taco Bar – Famous for margaritas and fresh tacos.
Pearl Restaurant – Stylish and modern with a seafood-forward menu.
Harry Browne’s – Upscale dining with a great view of the State House.
Middleton Tavern – Historic spot with oysters, a piano bar, and strong drinks.
Choptank – A lively rooftop bar with a relaxed vibe.
Where to Shop & Explore
The Market House – A lively food and shopping hub.
Cotton Company – A favorite for home goods and gifts.
The Lucky Knot – Nautical-inspired fashion.
Kim Hovell Gallery – Local art that captures the beauty of the Chesapeake.
Old Fox Books – A cozy bookstore with plenty of charm.
Maryland Avenue – A stroll here is a must for antique shops, boutiques, and historic atmosphere.
Where to Caffeinate & Indulge
Rise Up Coffee – Freshly roasted beans and a great local vibe.
The Red Bean Cafe – Perfect for both caffeine and dessert.
Brown Mustache Coffee – A hidden gem inside Old Fox Books.
Annapolis Ice Cream Company – Homemade ice cream made in-house.
Fun Extras
United States Naval Academy – Enter through the visitor gate and sign up for a guided tour. The guides are fantastic, and you’ll learn all about one of the country’s most distinguished military colleges.
Reynolds Tavern – Step back in time with high tea at the oldest tavern in town.
Summer Garden Theater – Outdoor performances under the stars.
William Paca House & Garden – A beautifully preserved 18th-century home with stunning gardens.
Hammond-Harwood House Museum – A gem of colonial architecture.
City Dock – Free summer concerts with waterfront views.
Eastport: Nautical Charm with a Local Vibe
Just across the bridge, Eastport feels like its own world — quirky, nautical, and full of local character. It’s the kind of place where you can eat incredible seafood in a casual setting and then watch the sunset from the shoreline.
Where to Dine & Drink
O’Leary’s – Intimate, upscale seafood that’s among the best in town.
Carrol’s Creek Café – Waterfront dining with stunning Spa Creek views.
Boatyard Bar & Grill – Legendary crab cakes in a lively setting.
Vin 909 – Wine, creative pizzas, and a cozy neighborhood vibe (go early!).
The Rum House – Island-inspired bites and cocktails. Get the oxtail stuffed pasta (I promise you will thank me later).
Blackwall Hitch – Rooftop views, fun décor, and regular live music.
Forward Brewing – A local brewery making inventive small-batch beers.
Where to Caffeinate & Indulge
Oscar’s Coffee – A pop-up shop with plenty of charm, named after a golden retriever.
Bakers & Co. – Weekend-only bakery with pastries worth the wait. Named “One of the finest little bakeries” by Food & Wine Magazine.
Fun Extras
J Port Annapolis – Rent a boat and see Annapolis from the water.
Eastport Backstreets – Stroll past quirky homes and maritime murals.
Sunset Views – Some of the best in town are from Eastport’s shoreline.
West Annapolis: Local Flavor Off the Beaten Path
Just beyond downtown, West Annapolis has a slower pace and a strong neighborhood feel. It’s full of hidden gems that many visitors never stumble upon.
Where to Dine & Drink
In Grano – A foodie favorite with an amazing wine list and creative cocktails.
Evelyn’s – Perfect for breakfast, brunch, or lunch.
Chessie’s Wharf – A brewery with excellent burgers and a laid-back riverside vibe.
Where to Caffeinate & Indulge
Bean Rush Coffee – Cozy and welcoming with great coffee.
Always Ice Cream – A fun, family-friendly stop for a sweet treat.
Fun Extras
Wardour Neighborhood – Wander or drive through this scenic riverfront community with some of the most beautiful homes in Annapolis.
Experiencing Annapolis Like a Local
What makes Annapolis truly special isn’t just the cobblestone streets or sparkling waterfront — it’s the way the city feels when you soak up the everyday magic that local’s cherish. This local’s guide highlights insider favorites, from tucked-away coffee shops to breezy sunset spots. And as you linger over brunch in West Annapolis, catch live music in Eastport, or tour the Naval Academy downtown, you’ll discover that Annapolis isn’t just a place to visit — it’s a place to belong, if only for a little while.