Upscale in Orlando

Wine Bar George

• ★ 4.8
• Wine bar
• $$$
• Disney Springs and Lake Buena Vista

Wine Bar George at Disney Springs is master sommelier George Miliotes' room with 100-plus wines by the glass and bottle, plus Mediterranean small plates.

Prato

• ★ 4.7
• Italian
• $$$
• Winter Park

Prato on North Park Avenue in Winter Park is the wood-fired Italian restaurant with house pastas, hearth pizzas and a long Italian wine list.

Hanson's Shoe Repair

• ★ 4.7
• Cocktail bar
• $$$
• Downtown Orlando

Drink Pearl Diver, Painkiller and rotating tiki classics

Hanson's Shoe Repair on East Pine Street downtown is the rooftop tiki speakeasy with a daily Instagram password, behind a Prohibition-style storefront.

Santiago's Bodega

• ★ 4.7
• Wine bar
• $$$
• Mills 50

Santiago's Bodega on Virginia Drive in the Mills Park complex pours Spanish wines and sherry alongside small-plate tapas and house charcuterie boards.

The Rusty Spoon

• ★ 4.6
• New American
• $$$
• Downtown Orlando

The Rusty Spoon on West Church Street downtown is chef Kathleen Blake's farm-to-table American room, a multi-year James Beard semifinalist nominee.

Kabooki Sushi

• ★ 4.6
• Japanese Sushi
• $$$
• Mills 50

Kabooki Sushi on East Colonial Drive is chef Henry Moso's modern sushi room with an omakase counter, an a la carte list and a Sand Lake second location.

The Courtesy Bar

• ★ 4.6
• Cocktail bar
• $$$
• Winter Park

Drink Rotating seasonal cocktails, classics with a twist

The Courtesy on North Orange Avenue in Winter Park is the long-running cocktail bar from Orlando, relocated to Winter Park with the same craft program.

SoCo Restaurant

• ★ 4.5
• Southern American
• $$$
• Thornton Park

SoCo on East Central Boulevard in Thornton Park runs a modern Southern menu with shrimp and grits, fried chicken and a covered weekend brunch patio.

Antonio's La Fiamma

• ★ 4.5
• Italian
• $$$
• Winter Park

Antonio's La Fiamma on South Orlando Avenue in Maitland is the family Italian restaurant with house pastas and an upstairs enoteca wine bar.

Lil Indies

• ★ 4.5
• Cocktail bar
• $$$
• Mills 50

Drink Technical classic cocktails, low-ABV highballs

Lil Indies on North Mills Avenue is the cocktail-craft sister bar to Will's Pub, with a moody back-room program and a shortlisted Mills 50 indie crowd.

Ravello at Four Seasons

• ★ 4.5
• Wine bar
• $$$
• Disney Springs and Lake Buena Vista

Ravello at the Four Seasons Resort Orlando runs an Italian restaurant and bar with an Italian-leaning wine program, breakfast antipasti and pasta service.

The Osprey

• ★ 4.4
• New American
• $$$
• Baldwin Park

The Osprey Tavern on New Broad Street in Baldwin Park is the New Broad modern tavern with wood-fired meats, house pastas and a smart bar program.

Linda's La Cantina

• ★ 4.4
• Steakhouse
• $$$
• Mills 50

Linda's La Cantina on East Colonial Drive is the family-owned steakhouse since 1947, with hand-cut steaks, garlic bread and an old-school dining room.

Wally's Mills Avenue Liquors

• ★ 4.4
• Cocktail bar
• $$$
• Mills 50

Drink Cold beer, well drinks and shot specials

Wally's on Mills Avenue is the city's enduring dive bar, family-run since 1954 with vintage wallpaper and a Mills 50 corner-of-Colonial-Drive location.

Quantum Leap Winery

• ★ 4.4
• Wine bar
• $$$
• College Park

Quantum Leap Winery on Edgewater Drive in College Park is Orlando's only urban winery, with full on-site production, Florida-grown grapes and a tasting room.

The Strand

• ★ 4.3
• New American
• $$$
• Mills 50

The Strand on North Mills Avenue is the seasonal American room from Alda and Joe Rees, with a changing menu, an excellent burger and cocktails.

The Monroe

• ★ 4.3
• Cocktail bar
• $$$
• Downtown Orlando

Drink Classic and modern craft cocktails

The Monroe on South Eola Drive downtown runs a craft cocktail program out of a Lake Eola corner restaurant, with a long bar and a Sunday brunch crowd.

Will's Pub

• ★ 4.3
• Cocktail bar
• $$$
• Mills 50

Drink Cold cans, well drinks

Will's Pub on North Mills Avenue is the longstanding Mills 50 indie-music dive bar, with a nightly live band calendar and a checkered indie booking history.

Bosendorfer Lounge

• ★ 4.3
• Cocktail bar
• $$$
• Downtown Orlando

Drink Signature European cocktails and Champagne flights

Bosendorfer Lounge in the Grand Bohemian Hotel downtown is the second-floor jazz cocktail lounge with a Bosendorfer grand piano and European cocktails.

The Imperial Wine Bar

• ★ 4.3
• Wine bar
• $$$
• Downtown Orlando

The Imperial Wine Bar on North Orange Avenue in Ivanhoe Village is the wine bar inside Washburn Imports, a furniture showroom turned neighborhood favorite.

Stardust Lounge

• ★ 4.2
• Cocktail bar
• $$$
• Downtown Orlando

Drink Classic cocktails, vintage tiki, frozen drinks

Stardust Lounge on East Central Boulevard downtown is the retro Lake Eola cocktail lounge, with vintage drinks, velvet booths and a Tue-Sat calendar.

The Imperial at Washburn Imports

• ★ 4.2
• Cocktail bar
• $$$
• Downtown Orlando

Drink Boutique wines plus craft Florida beers

The Imperial on North Orange Avenue inside Washburn Imports furniture showroom is the late-night neighborhood wine and craft beer bar with charcuterie.

Mathers Social Gathering

• ★ 4.2
• Cocktail bar
• $$$
• Downtown Orlando

Drink Classic cocktails, prohibition-era reproductions

Mathers Social Gathering on South Magnolia Avenue is a third-floor downtown lounge inside the Mathers Building, with a velvet-banquette speakeasy aesthetic.

Ciao Italia

• ★ 4.1
• Italian
• $$$
• ICON Park and I-Drive

Ciao Italia on Westwood Boulevard in the Sand Lake dining strip is the family Italian restaurant with classic Italian-American dishes and a house wine list.

Canvas Restaurant and Market

• ★ 4.1
• New American
• $$$
• Lake Nona

Canvas Restaurant and Market on Sachs Avenue in Lake Nona is the lakefront American room with a covered patio, a wood-fired hearth and Sunday lake brunch.

House of Blues Orlando

• ★ 4.1
• Cocktail bar
• $$$
• Disney Springs and Lake Buena Vista

Drink Blues-bar classics, frozen hurricanes

House of Blues Orlando at Disney Springs runs a Southern American kitchen and live blues music venue, with the Sunday Gospel Brunch as the brand standard.

The Robinson Room

• ★ 4.1
• Cocktail bar
• $$$
• Downtown Orlando

Drink Classic cocktails, prohibition-era list

The Robinson Room on East Pine Street downtown is the cocktail lounge with a Prohibition-era list, leather booths and a late-night downtown crowd.

The Glass Knife

• ★ 4.1
• Wine bar
• $$$
• Winter Park

The Glass Knife on South Orlando Avenue in Winter Park is the patisserie and wine bar with Champagne flights, dessert pairings and a full dinner program.

The Boathouse

• ★ 4.0
• Seafood
• $$$
• Disney Springs and Lake Buena Vista

The Boathouse at Disney Springs is the dockside American seafood restaurant with raw bar, lobster rolls and Amphicar lake tours of the Disney Springs lake.

The Bull and Bush Pub

• ★ 4.0
• Cocktail bar
• $$$
• Thornton Park

Drink Pints of British ale, Guinness and house specials

The Bull and Bush Pub on East Robinson Street near Thornton Park is the British-style neighborhood pub with a fish and chips kitchen and weekend trivia.

Ole Red Orlando

• ★ 4.0
• Cocktail bar
• $$$
• ICON Park and I-Drive

Drink Country-style whiskey cocktails, frozen margaritas

Ole Red Orlando on International Drive at ICON Park is the Blake Shelton country bar and restaurant, with three stories, daily live music and barbecue.

Swirlery Wine Bar

• ★ 4.0
• Wine bar
• $$$
• Milk District

Swirlery on East Michigan Street in the Hourglass District is the self-serve enomatic wine bar with dozens of wines by the ounce, cheese boards and a patio.