San Francisco feels like a Petri dish for new business plans. Half the internet billionaire geniuses seemed to have passed through it in the past decade; cars are plugged in, billboards laud the benefits of Bitcoin and locals join a waiting list to fly into space. There’s a thriving restaurant scene (even the airport is sourced with organic local food) and the city boasts a pair of the world’s great urban parks – Golden Gate and the Presidio – all packed into a thumb-shaped peninsula. Surrounded on three sides by water, San Francisco is a kind of island state; a steep-sloped, diverse and beautiful cityscape brimming with gourmet offerings. With the right footwear, it’s paradise.
Stop and smell the roses
07:00 Wake like a true San Franciscan and check the sky. Rains, wind and fog can invade without notice so dress in layers. Given the steep hills, it’s little surprise that alternative car-hire services Lyft and Uber were born here. When cable cars, Muni buses or BART subways aren’t an option, use the cars for short, inexpensive trips or arrange a custom two-hour rental (roughly $65). Reserve a table with a view at Cliff House for 9am and head for Twin Peaks via a ski-trail-like road that swirls you 300 metres above the city. Follow the signs from the car park to South Peak (Noe) for panoramic views. Next stop is Golden Gate Park via the Conservatory of Flowers, a glass-paned greenhouse designed like a fairytale fantasy home. Explore the manicured flowerbeds and imagine the sea of sand dunes that existed before architect Frederick Law Olmsted (who also designed Manhattan’s Central Park) created a labyrinth of romantic nooks and crannies. Drive the five kilometres down to Ocean Beach. When you see the four-storey Dutch Windmill, you’re about to hit the stiff wind coming off the beach. Turn right (north) on the Great Highway for your overdue breakfast stop.
Breakfast from on high
09:00 Cliff House is an old-school restaurant that won’t win awards for décor (those drapes!) but it offers extraordinary views and the food is excellent. Try its classic Eggs San Francisco, which includes the city’s signature sourdough bread with poached eggs and crab. Afterwards, walk up to Lands End Lookout, the visitor centre and trailhead for exploring the World War II batteries, shipwrecks and beachfront paths.
11:00 Order a car and take a 6.5-kilometre drive north through the Presidio, a former military base that became a park in 1994. The officers’ quarters now house not-for-profit organisations and the Presidio’s thickly wooded areas offer yet another escape from the bustle of the city. Continue down to the former airstrip known as Crissy Field, where – if you’re lucky – the fog will have lifted enough for a view of Alcatraz. If you need a caffeine boost, look for the Philz Coffee truck then stroll out to Fort Point, an army installation built in the 1850s to defend California’s goldfields from enemy attack. The brickwork is considered among the finest west of the Mississippi and if you study the Golden Gate closely you can see how the bridge arches up to accommodate this gem of a building. The fort has a great gift shop.
12:00 Walking across the Golden Gate Bridge is easier than it sounds. The wind can be blustery and on weekends it’s crowded but the 2.7-kilometre walk is worth the effort. On the north side, hike up a small hill to Hendrik Point, where you can rest while taking in San Francisco’s skyline, framed by the arches of the Golden Gate.
14:00 Few neighbourhoods have more sun than the Mission District, an area known for its rich Latino history, murals, nightlife and Tacolicious, hipster HQ for a Southern California-style taco. It’s a 20-minute drive (let the driver figure out the mad local traffic) and once there, order a margarita fresca, spiked with blood orange and cardamom, and owner Joe Hargrave’s speciality: a guajillo-braised-beef short-rib taco. Nearby is the oldest-surviving building in the city – Misión San Francisco de Asís. Don’t miss the 1830s-era cemetery, replanted with species of plants and trees native to the area. The guided tour provides a glimpse of life during the early Spanish conquest of California. Overall, it’s a half-hour stop at the mission for which the city is named.
Pride of place
16:00 Walk up 16th Street until you reach the corner of Castro Street and you have made it to the heart of San Francisco’s thriving gay and lesbian neighbourhood. Straight or gay, you’ll enjoy street life in The Castro. This area is a tribute to tolerance and a reminder of the struggle to achieve it. Pioneering gay politician Harvey Milk, who was assassinated in 1978, lived at 573 Castro Street. His home, complete with a mural, is now an informal shrine. For a more complete history of the district’s role in expanding civil rights, visit the GLBT History Museum at 4127 18th Street (closed on Tuesdays). There’s eclectic shopping in The Castro, including iconic goodies at Hot Cookie (407 Castro Street) and, half a block down the road, the world’s wackiest hardware and more at Cliff’s Variety (479 Castro Street). Architecture buffs will love the restored Victorian homes, with ridiculously elaborate paint jobs, which you can admire as you’re leaving the quirky neighbourhood on the vintage streetcar (F-line) that goes down Market Street.
Escape to Alcatraz
18:00 After spotting Alcatraz Island in the middle of the bay, you might be wondering: should I go? The answer is yes. But visiting one of the world’s most famous prisons can be as challenging as trying to escape. Tours are often sold out two months in advance. Reserve your spot well ahead and be sure to select the unique night excursion, which offers stunning views of San Francisco and a kitschy but still scary “lockdown”, where visitors are placed inside the cells.
Steak of epic proportions
21:00 From the ferry docks of Fisherman’s Wharf, go west to Epic Steak, a sleek steakhouse with views of the Bay Bridge, alit at night, and an extensive selection of quality cuts. Epic is a brilliant punctuation mark to the day.
Social (media) drinking
23:00 If you’re still going, drop in to Dirty Water, the spacious bar buried in the bowels of Twitter’s world headquarters. With 52 beers on tap and Twitter employees still kicking back after a hard day’s work, it’s a great place to chat to strangers and feel the dynamics of a city that continues to upend both the present and the future.