It’s no coincidence that some of the world’s most innovative tech companies (eg. Google, Apple, Uber and Airbnb) were conceived just a stone’s throw away from the bayside splendour of San Francisco. Thanks to nearby Silicon Valley’s wealth of tech millionaires, the Bay has earned its reputation for being the second most expensive city to live in (after New York, of course), but the city’s expansive, historically hippie tendencies lend the Golden Gate town an air of progression and eclecticism. And unlike other waterside cities (ahem, Sydney), San Francisco is relatively small and easy to navigate, thanks to a network of cable cars and grid-lined streets.

You’d be hard-pressed to find a more conveniently located stay in town. A San Francisco institution, it places you smack bang in the Theatre district, close to Chinatown, Nob Hill and Union Square (aka shopping nirvana). Be sure to take the elevator to the top floor, where the Cityscape Bar and Lounge offers the best 360-degree views of the city, cocktail in hand. Hilton San Francisco Union Square Hotel, 333 O’Farrell Street, San Francisco

Hilton’s local café is attached to the Union Square hotel, so naturally by 7am it’s usually overflowing with travellers tucking into the buffet breakfast. In the pm, however, it transforms into an intimate restaurant boasting gastropub favourites such as Brandt Beef Bavette steak, pork chops, Garganelli pasta Bolognese and shaved Brussells sprouts with candied bacon and blue cheese vinigarette (a highlight). It uses sustainably sourced produce where possible and carries a 50-plus wine menu also worth perusing. 333 O’Farrell Street, San Francisco, urbantavernsf.com

This cosy eatery offers a slice of Parisian cuisine in the heart of San Fran. With French bistro favourites like steak frites, escargot and confit on the menu, if you’re lucky, you might even score the full French hospitality experience with a table visit from the so-Parisian-its-funny restaurant manager Olivier. In addition to its cosy ambience, Café de la Press also carries an impressive number of international magazines on its newsstand. Surprising and charming. 352 Grant Avenue, San Francisco, cafedelapresse.com

Number 37 in The World’s 50 Best Restaurants list, Saison might have lofty credentials, but it leaves all the fancy footwork for the chefs in the kitchen. Touted as a casual dining space, they play rock music and there’s no dress code, leaving the rotating menu of 18 courses the real hero of this joint. Bring your shiniest credit card; this three-Michelin starred restaurant is both exclusive and heavy hitting on the purse strings. 178 Townsend Street, San Francisco, saisonsf.com

Short on time but want to see San Fran’s main attractions? As daggy as it may sound, a city tour can take the effort out of the sightseeing equation – particularly if you’re only in the area for a few nights. Be sure to hit up the beautiful Golden Gate Park, bohemian district Haight Ashbury (the former residence of Jimi Hendrix and Janis Joplin), seaside area Land’s End and, if you’re really into Instagram-worthy sights, the famous winding road at Lombard Street and the Painted Ladies (above) on Steiner Street. Crowded, but fun. Try: Tower Tours, towertours.com

Eerie and thought-provoking, a tour of the Bay’s famous island penitentiary is one way to kill a few hours while brushing up on the city’s history. Once the home of famously slippery prisoners such as Al Capone and James ‘Whitey’ Bulger (the subject of the 2015 film Black Mass), a walking audio tour of the prison details the many escape attempts and exploits of some America’s most notorious inmates. Well worth the ferry trip. Try: alcatrazcruises.com

Right in the heart of Golden Gate Park stands this science and natural history museum teeming with cool finds. From butterfly enclosures to a ground-floor aquarium and, weirdly, a lone albino alligator (*insert sad face*), an afternoon spent here is a bit like revisiting the wonder of your childhood – in the best way possible. Golden Gate Park, 55 Music Concourse Dr, San Francisco, calacademy.org

Directly opposite the California Academy of Science (a pretty park separates the two buildings) lies de Young – an immersive, contemporary art experience. With exhibitions like The Summer of Love Experience: Art, Fashion, and Rock & Roll on show for 2017, plus a permanent collection housing an impressive array of American artists (Diego Rivera, Georgia O’Keeffe, Edward Hopper, Mark Rothko, Willem de Kooning and more) from the 17th century to the present – it’s one way to dip your toe into some American cultural history. Don’t miss the observation platform – it boasts a panoramic view of the entire Bay Area. Golden Gate Park, 50 Hagiwara Tea Garden Drive, San Francisco, deyoung.famsf.org

Any fool with a credit card knows that American department stores are where it’s at. But Union Square has that and more. From Saks Fifth Avenue to Tiffany & Co., Apple, Victoria’s Secret, Macy’s and Uniqlo; the shopping precinct presents hours of potentially dangerous retail fun. Bonus: the square doubles as a giant ice skating rink in winter. Cool.

For a quick lesson in exactly how Americans scored their reputation for doing everything supersize – head on to Fisherman’s Wharf. As the name suggests, this series of waterfront locations has uninterrupted views of the bay… not to mention countless ways to exceed your daily calorie limit in one sitting. Stroll through the kitschy carnival attractions at Pier 39 and stop for a moment to watch (and listen) to the sea lions who like to sunbake on the deck.

This landmark is to San Fran what the Harbour Bridge is to Sydney – a clichéd, yet totally unmissable icon. Do your butt a favour and hire a bike at Fisherman’s Wharf and cycle the bridge. The uphill portions of the ride might be a killer thigh workout, but the view (from far away to ‘Now-I’m-on-the-bridge!’) makes up for your aching muscles. Trust me, I hate bike riding, but the photos were worth it. Once you’ve cycled the bridge, follow the road to the pretty suburb Sausalito, where you can catch the ferry back with your bike and end up right where you started. Don’t forget to jump on one of San Fran’s famous trams, too! Yeong Sassall travelled to San Francisco as a guest of Hilton Hotels & Resorts.