Graduate by Hilton Annapolis

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

Bakers & Co. is a charming family-run bakery in Eastport serving up irresistible pastries, fresh breads, and coffee, but be ready to line up on weekends!

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.

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.

Davis’s Pub, a cozy neighborhood gem since the 1920s, boasts irresistible crab cakes and charming vibes, making it a must-visit in Annapolis.

Dry 85 is a chic and cozy bourbon bar in downtown Annapolis, serving up a killer selection of over 100 whiskeys alongside inventive comfort food delights.

Nestled in Eastport, Forward Brewing is a cozy neighborhood spot serving artisanal beers and delicious bites, all in a laid-back, dog-friendly atmosphere.

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!

Elegant, Georgian-style inn offering 3 refined rooms & suites, plus a tearoom & an old-world pub.

Experience top-notch private sailing tours that offer expert insights into harnessing the wind and navigating the waves like a pro.