This vintage wine bar/restaurant is a Sydney classic. Small but immensely atmospheric, it offers an Italian-influenced snacking-style menu that’s a perfect fit for the beautifully curated, mostly Italian, mostly natural wine list. It’s a venue that never goes out of fashion. Be sure to try the famed whipped bottaga and pretzel, and the pasta dishes are also excellent.
This extraordinary Italian restaurant has occupied a stately corner on Boundary St since 1987. Now in the hands of chef David Wright, who trained under the original maestro Armando Percuoco, it remains a fabled part of the fabric of Paddington, serving classic Italian food including its famed fettuccine al tartufovo — pasta with cream and parmesan topped with a fried truffle egg.
This traditional Italian restaurant has been a mainstay in Elizabeth St for more than a decade. Its secret? Locals love it. Generous, authentic food, caring service and genuine Italian warmth make Cipri a destination venue for a legion of loyal fans. Its sister cafe, Barbetta, right nearby is also a local’s favourite.
Civico 47 had big shoes to fill, stepping into the space occupied grandly by Lucio's restaurant for four decades. But the change has been embraced in Paddington, with the newcomer finding an audience attuned to its modern take on Italian food. Chef Matteo Zamboni tweaks Italian classics to bring his own dash to dishes such as beef carpaccio with rocket, macadamia, vincotto and Brussels sprouts. The stylish, understated room and leafy location are widely admired.
American chef Danielle Alvarez is no longer at the helm of this Oxford St favourite but her imprimatur remains in the DNA of this exceptional restaurant. Alvarez was all about seasonal good produce, done simply and well, served in this gloriously restored space. Things haven’t changed much since her departure, so expect soulful food and quality service in one of the suburb’s loveliest dining rooms.
Nestled into the rear rooms of the Paddo Inn — but entered via William St — Il Baretto was a longtime Surry Hills favourite before relocating to Paddington in 2020. The Italian menu is concise and packed with classics such as calamari fritti and veal meatballs, and locals can’t get enough.
Marcello Farioli hails from Modena in the Italian province of Emilia-Romagna and brings his region’s passion for fine food and wine to Paddington-Woollahra. Dine in the sweet front rooms or upstairs with their Jersey Rd aspect to enjoy authentic dishes that include Farioli’s signature handmade pastas offered with quality regional wines.
It looks modest from the outside, but journey into this organic-forward pizzeria to find a substantial outlet that runs the roomy length of this Oxford St terrace space. The pizzas are the drawcard here — all Neapolitan-style fluffy bases and quality ingredients — but the pasta dishes are also enticing. Love Supreme is a step up from the other pizzerias in the area.
Head up the stairs from the cult bottle-o P&V Wine + Liquor to find this engaging and well-priced French bistro. You could miss it from the street, but Porcine has developed a formidable reputation for chef Nicholas Hill’s pork-forward menu of dishes that include Berkshire chop with celeriac and tarragon mustard. It’s only open from Thursday to Sunday so book ahead.
This excellent Latin-American venue is a local’s favourite with a big reputation that’s well deserved. The menu is a unique blend of Latin American flavours from Mayan, Aztec, Spanish, Portuguese, Nikkei, Chifa and Colombian Afro Caribbean influences with an emphasis on bold, fresh flavours, driven by quality, seasonal produce, enhanced by cooking over wood and charcoal. Try dishes like tuna ceviche, spatchcock 'Ají de Gallina' and steak with merquén butter and pickled shiitake. The margaritas and other Latin-inspired cocktails are also brilliant.
Inhabiting a grand corner terrace that has been a restaurant site for 50 years, chef Phil Wood’s new restaurant dabbles in nostalgia through dishes such as snapper with a Keen’s curry vinaigrette, and peach Melba. Destined to be a neighbourhood favourite, it is a venue with a heart and soul.
Cheerful and unpretentious, this family restaurant offers quality pizza and pasta in a buzzy environment. Come with a group of friends or extended family and leave happy and sated with your soul full of Italian spirit. On warm nights, sit out front to enjoy the Five Ways passing parade.
This brick-lined bar, restaurant and bottle shop at the top of Oxford St offers great food and excellent drops. One of Sydney’s original wine bars, it has 700 wines by the bottle and 65 by the glass including rare, aged and old vintage wines. Pull up a stool for a quick tipple or settle in for rare and interesting wines to suit your tastes.
Originally opened as a café, Zafferano has found success since reinventing as a trattoria in 2022. The restaurant sources inspiration from Sicily and is named after a province where chef and co-owner Simone Crivello learned to cook. So find a seafood-heavy menu with dishes such as fish sautéed with tomatoes. On sunny weekends, tables are set up outside under umbrellas for an authentic Mediterranean-in-Paddo feel.