Monica

Perched five floors above Oxford Street, Monica brings a dose of West Hollywood energy to Paddington. Sitting atop 25hours Hotel The Olympia, the rooftop bar combines sweeping views across the eastern suburbs and Sydney skyline with a drinks-first menu designed for long afternoons that drift into late nights.

The 200-seat venue is one of four hospitality concepts inside the landmark hotel, with culinary director Mitch Orr and drinks lead Roean Patawaran shaping an offering that leans heavily into share-style snacks, easy-drinking cocktails and a distinctly social atmosphere. Inside, tiled bars, striped awnings and lounge seating nod to classic California hotel culture, while the outdoor terrace delivers front-row seats to sunset over the city.

Orr's signature lightly devilled crab arrives with Jatz crackers, while soy-cured tuna, fried rice cakes, cold noodles dressed in ponzu and sesame, and dry-aged beef burgers round out the offering. Larger plates sit comfortably alongside snackable bites, making Monica suited to both a quick drink and a full afternoon session.

Naturally, however, cocktails are the headline act. Expect playful takes on classics, from spicy Picante Margaritas to fruit-forward daiquiris and a Mimosa service designed for groups. The wine list spans local and international producers, while beers remain approachable, with a mix of Sydney favourites and global staples.

A rotating roster of DJs brings the space to life throughout the week, turning Monica into one of Paddington's most animated rooftop destinations. Whether you're dropping in for golden hour drinks, a midweek catch-up or a weekend celebration, the appeal remains the same: good cocktails, open skies and a view that reminds you why Sydneysiders are so obsessed with rooftops.

Image credit: Steven Woodburn | Supplied