Vin 909 Winecafe'

This cozy Irish pub in historic Annapolis serves hearty Gaelic fare and boasts an impressive whiskey selection, all wrapped in a warm, inviting atmosphere.

Nestled in a historic bank on Capitol Hill, Acqua Al 2 offers an upscale Italian dining experience with homemade pastas and a lively speakeasy below.

The Choptank is a vibrant seafood haven where Maryland classics meet live music and breathtaking waterfront views, perfect for a memorable dining experience.

This cozy, seasonal seafood spot offers fresh catches from the bay at picnic tables outside, making it a perfect low-key eatery for a breezy evening.

Nestled on the waterfront, this vibrant Caribbean eatery offers fresh flavors, fun cocktails, and live music with stunning views in Annapolis.

Nestled in downtown Annapolis, this historic 1870s brick Governor's Mansion dazzles with stunning architecture and vibrant local charm.

Boatyard Bar & Grill is a bustling nautical gem in Annapolis, serving unbeatable crab cakes, fresh oysters, and a relaxed vibe perfect for seafood lovers.

Chick & Ruth's Delly is a lively, vintage diner in Annapolis, known for its massive crab cakes and quirky decor, serving all-day breakfast and hearty sandwiches amidst a warm, bustling atmosphere.

This stylish waterfront hotel boasts stunning views of Annapolis Harbor, modern rooms, and a tropical vibe, making it a prime spot for relaxation and exploration.

Nestled in downtown Annapolis, this cozy café offers a laid-back vibe with stellar coffee, hearty American bites, and live music to set the scene.