Acqua al 2 Main Street

Romantic Tuscan restaurant offering pasta flights, steaks, and an extensive wine list (The only other location of this restaurant is 1 block from Maddy and Alec's apartment in Florence).

Sailor Oyster Bar West Street

Trendy raw bar with oysters, crudo, and small plates—served in a cozy, industrial-chic space.

Fox’s Den Main Street

Underground gastropub offering wood-fired pizza, craft cocktails, and a stylish setting.

Boatyard Bar & Grill Eastport

Local favorite for hearty seafood fare, raw bar, and a laid-back nautical vibe (The couple's favorite crabcake).

The Choptank Harbor

Lively waterfront crab house with steamed crabs, seafood classics, and a spacious outdoor deck.

Vida Taco Bar Main Street

Creative street-style tacos and margaritas in a fun, casual setting right on Main Street.

Vin 909 Winecafé Eastport

A charming farm-to-table pizza and wine bar just across Spa Creek in Eastport, known for its wood-fired artisan pizzas, seasonal fare, and excellent local wine list.

Iron Rooster Harbor

An all-day breakfast and brunch favorite, known for homemade pop-tarts, southern comfort food, and a welcoming, family-friendly vibe.

The Point Crab House & Grill Outside Downtown

A scenic waterfront spot located just outside downtown Annapolis in Arnold, MD. Known for its fresh Chesapeake seafood, laid-back vibe, and beautiful views of Mill Creek (Maddy's summer employer in high school and college).

Galway Bay Irish Restaurant & Pub Maryland Ave

A beloved downtown Annapolis Irish pub known for its award-winning whiskey list, traditional dishes like fish & chips and shepherd’s pie and genuine Irish hospitality.

Carrol’s Creek Cafe Eastport

Upscale waterfront dining with refined American seafood and great views of Spa Creek.

Harry Browne's Maryland Ave

A classic Annapolis restaurant known for its elegant American cuisine, Chesapeake flavors, and charming views of the Maryland State House.

The Goat Harbor

Modern Latin-American fusion spot with bold flavors and a colorful, upbeat vibe.

Middleton Tavern Harbor

Historic 1700s tavern serving Maryland seafood favorites like crab cakes and mussels.

Reynolds Tavern Main Street/ West Steet

Colonial-era tavern with traditional pub fare, afternoon tea, and beautiful outdoor seating.