Charley's Steak House

The Restaurant

Charley's Steak House opened on West Cypress Street in 1974 and has been a Tampa institution ever since. The current building is a freestanding, wood-and-stone structure designed around its open-fire kitchen — diners can watch prime cuts being seared over a custom Argentinian-style citrus-wood grill from the main dining room. The restaurant has held a Wine Spectator Grand Award (the publication's highest tier) every year since 1985, one of only a handful of independent steakhouses in the country with that streak.

The cellar is the talking point. Roughly 2,400 references — heavy California Cabernet, a Bordeaux programme that includes vertical runs of First and Second Growths, a deep Italian section, and a serious Burgundy bench — make this one of the most ambitious wine lists in Florida. The wine team includes three Court of Master Sommeliers Certified Sommeliers and a full-time cellar master. Bottle markups at the top end are conventional steakhouse rates (2.5–3x retail), which makes the deeper cellar selections genuinely useful, not theatrical.

The cooking is steakhouse classical with no experimental flag-waving. Prime cuts are wet-aged 28 days, dry-aged cuts available on weekly rotation, and the over-fire technique gives a char that contemporary steakhouses with electric grills cannot match. The bone-in 22oz cowboy ribeye, the 16oz dry-aged New York strip, and the chateaubriand for two are the cellar pulls. Side dishes are large; the lobster mashed potatoes have been on the menu for two decades.