Steakhouse$$$$harbor-eastBook 1 to 2 weeks ahead
The Bygone tops the Four Seasons on the 29th floor, a 1920s-style room serving steaks and seafood with panoramic views over the Inner Harbor.
Order: A steak or seafood tower, with a window table at golden hour.
Tip: Ask for a window seat; the 29th-floor harbour view is the reason to come up.
American fine diningChef Cindy Wolf$$$$$129 and up by course countharbor-eastBook 2 to 4 weeks ahead
Charleston is Cindy Wolf's Harbor East flagship, a 2025 James Beard winner for its beverage program, where you build a Lowcountry menu course by course.
Order: Build the menu around the cornmeal-fried oysters and shrimp and grits.
Tip: It is the city's benchmark special-occasion room; the wine pairing draws on a vast cellar.
Seasonal AmericanChef Scott Bacon$$$$mount-vernonBook 2 weeks ahead
Magdalena inside the Ivy Hotel is chef Scott Bacon's seasonal American bistro, plating a changing canape board and Chesapeake plates in a stone mansion.
Order: Whatever lands on the changing canape board, then a seasonal main.
Tip: It sits inside the Relais and Chateaux Ivy Hotel; reserve for the courtyard in warm months.
ItalianChef Cindy Wolf$$$$harbor-eastBook 1 to 2 weeks ahead
Cinghiale in Harbor East is Tony Foreman and Cindy Wolf's northern Italian enoteca, pairing house-made pasta and magret of duck with a deep Italian list.
Order: A plate of house-made pasta and the magret of duck.
Tip: The osteria side takes walk-ins; the enoteca dining room is the full kitchen experience.
Italian steakhouseChef Julian Marucci$$$$harbor-eastBook 1 to 2 weeks ahead
Tagliata in Harbor East is Atlas Restaurant Group's Italian steakhouse, where chef Julian Marucci plates squid ink campanelle with blue crab and uni cream.
Order: The black squid ink campanelle with blue crab and uni cream.
Tip: The dim, clubby room books out on weekends; the bar takes walk-ins for pasta.
Steakhouse$$$$mount-vernonBook 1 to 2 weeks ahead
The Prime Rib in Mount Vernon is a 1940s-style supper club with leopard carpet and a piano, serving the city's benchmark prime rib in black tie.
Order: The prime rib, with the Greenberg potato skins.
Tip: Jackets are required for men; a pianist plays nightly in the lounge.