Sailor Oyster Bar

RaR Brewing's Chessie's Wharf in Annapolis is your go-to spot for craft brews, tasty bites, and a vibrant outdoor patio that welcomes families and pups alike!

Located on bustling Main Street, Preserve offers a cozy spot where pickled and fermented delights shine in creative American dishes—perfect for date night or casual dining.

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.

Vida Taco Bar is a trendy spot in downtown Annapolis where you can enjoy vibrant, creative tacos and strong, refreshing margaritas in a lively atmosphere.

A cozy hybrid café in the Arts District, this spot serves up top-notch coffee, delectable pastries, and charming bites, perfect for any time of day.

This chic Italian hotspot serves up exquisite Tuscan dishes and delicious brick-oven pizzas, all in a warm, inviting atmosphere with top-notch service.

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.

Pip's is a low-key hot dog stand in downtown Annapolis, renowned for juicy cheesesteaks, outstanding chili dogs, and friendly service.

Vin 909 is a cozy Eastport gem serving creative farm-to-table American fare and outstanding pizzas, all paired with an impressive wine list.

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.