The City by the Bay has been a source of inspiration to all variants of people since it came to the world’s attention in the mid 20th century. From the formation of the United Nations to the social liberalisation that led to the hippie-prompted Summer of Love in 1967, San Francisco has long been a place of liberal activism, attracting and continuing to magnetise an eclectic mixture of people. Now a popular lure for tourists, there’s a wealth of sights and activities to entertain and satisfy curious minds. From the Golden Gate Bridge to Alcatraz, Fisherman’s Wharf and the painted ladies, it’s evident why people continue to visit this boomtown, year in, year out.
If you’re hard pressed for time, I’ve devised (along with the help of Boston-based friends) a 24-hour itinerary that covers a large portion of the most prominent sights. Don’t forget to leave your inhibitions behind, bring a little of your freak and wear flowers in your hair while traipsing the streets and riding the trolley from Embarcadero to the Castro. You may never leave.
Morning – Artisans and Hangouts
Before fuelling the hunger fire, take an iconic ride on the Powell-Mason Cable Car up – and partway down – one of the city’s many steep streets. Starting at the turnaround on Market and Powell, you’ll travel facing the passing facades before getting off at stop 15370 (at the intersection of Mason and Vallejo).
Kickstart the rest of your day in boomtown by throwing down a powerful espresso – or suitable alternative – at Caffe Trieste, a North Beach institution that’s inspired bohemians since its establishment in the booming fifties. It’s the place where The Godfather was penned and it’s where Jack Kerouac gathered with other writers of the post-war Beat movement. Walk a few metres along the road to the likes of Al’s Attire, a homage to rockabilly apparel. Follow it up with a visit to the kitty-corner paired stores, 101 Music. There are gems to be found, more so in the basement: unsorted perennial records go for $5 a pop.
It’s here that a sliding door occurs: Coit Tower – with its unparalleled panoramic city views - is close, but in the opposite direction to the sights in the following few paragraphs. If you want to skip the next five attractions (from City Lights Bookstore to Wingtip), then visit Coit Tower after 101 Music, following which you should take the Greenwich steps from Montgomery Street of Telegraph Hill to Greenwich Street and turn right onto the Embarcadero, walking twenty-five minutes to the Ferry Building Marketplace.
Head to literary landmark City Lights, the Ferlinghetti bookstore famous for its Beatnik overtones, evident in anti-authoritarian political titles on the shelves. For a moment of intimacy, go to the third floor, pull out a copy of Howl and pause in the Poet’s Chair to ponder its significance.
Mid-Morning – History and Flavour
Pass through Jack Kerouac Alley and muse over poetic insignia and murals en route to Chinatown. It’s here, among the pagoda gables, that you’ll find Golden Gate Fortune Cookie Company, a one-room establishment that pumps out the famous treats. Write your own fortune and buy a jumbo cookie to satiate a growing pre-lunch appetite. For a sample of oriental-style dim sum, City View should be next. Steamed, baked and deep fried, there’s a dish available for every type of tastebud.
Burn off the cookie calories en route to Wingtip, “A 21st century interpretation of the classic social club.” A club-cum-store in an iconic Financial District building, clothing, accessory and grooming solutions are charmingly curated for modern men.
It’s time to see the bay and a historic piece of San Francisco waterfront iconography: the dramatic clock tower, attached to the Ferry Building Marketplace. Wander inside and mooch over communities of artisan food and observe a food revolution in progress. Select a bitesize comestible from a gourmet vendor and savour its organic flavours as you wander – or take a vintage streetcar (aka cable car/trolley) - along the Embarcadero to Pier 39.
Sea lions congregate on K-Dock, barking boisterously for the listening pleasure of attentive throngs of tourists. The migratory pinnipeds will continually wiggle their way into new positions as you meander from shop to shop, avoiding the temptation to pause at Bubba Gump Shrimp Co.
Lunchtime – Fantasies of Fodder
Let the aroma of Fisherman’s Wharf (a short stroll along Jefferson Street) entice you. Once the main port entry to the city, the buzz of modern activity is a contrast to the clamour originally created by the meeting of land and sea. Seafood, American and Italian options abound, so follow your nose and pull up a pew in the open air for lunch.
Another sliding door moment occurs here, with the option of going to the historic island of Alcatraz for the afternoon (with ferries departing every thirty minutes from Pier 33) rather than following the rest of this itinerary. The choice is yours, of course.
Afternoon – Rainbows and Panoramas
Board the vintage $2 F streetcar along Embarcadero and travel through history via Market Street to The Castro, the mother – or father - of the rainbow flag. Pass the Castro Theatre – closely observing showtimes – and pause at the intersection of 18th and Castro. It’s here where history was and is continually made, events, marches and protests held in the name of LGBTQI rights. Turn around, head due north along Castro Street - collecting a coconut macaroon from The Hot Cookie Bakery on the way – and walk in Janis Joplin’s vintage shoes for a while along Haight Street.
The painted ladies await, the iconic Victorian ‘Postcard Row’ featured in the long-running series’ Full and Fuller House. Take a snap, then walk to the corner of Divisadero and Geary Boulevard where you can take bus 38 to Lincoln Park. What better place than Lands End Lookout from which to capture the essence of San Francisco: over the rolling bay to the eternal rubicund glean of the Golden Gate Bridge. Take the trail further through the park and Sea Cliff neighbourhood to China Beach, in time for sunset.
Evening - Considered and Carefree
There are endless dinner options scattered through the city so, ask around, make some friends and follow your newly liberated heart.
